25 Incredible Weekend Getaways from Boston

There are so many exciting weekend getaways from Boston that deserve a spot on your bucket list.

Depending on how far you are willing to drive, there are many places in Massachusetts, Vermont, Maine, New Hampshire, Rhode Island, Connecticut, and New York that are perfect for short visits. 

Whether you’re looking to escape to the mountains or the seaside, visit historic towns, go museum hopping, or crave an assortment of experiences, pick from among these following towns, and discover the perfect weekend getaway for yourself.

BEST WEEKEND GETAWAYS FROM BOSTON
Massachusetts
Maine
New Hampshire
Vermont
Rhode Island
Connecticut
New York

Massachusetts (MA)

Sunset colors over a boardwalk leading to the beach in Plum Island near Newburyport Massachusetts
Sunset views at Plum Island, near Newburyport, MA

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Newburyport 

Drive time from Boston to Newburyport: 53 minutes

Located 35 miles north of Boston, Newburyport is a charming coastal town with several small restaurants, stores, breweries, and maritime history. 

Perhaps the two biggest attractions in the town are Parker River Wildlife Refuge which is home to over 300 species of resident and migratory birds, and Plum Island Beach, which is an 11-mile long white sand beach with breathtaking views of the Atlantic Ocean. 

The refuge is on Plum Island and also has beach access.

Once you enter Plum Island, you can pull over at one of the different parking lots along the route.

While you are here, you can also visit the Plum Island Lighthouse located at the northern end of the island.

Culture lovers will enjoy the collection of maritime art, model clipper ships, and displays from infamous shipwrecks at the Custom House Maritime Museum in Newburyport. 

Nature-lovers should visit Bartlett Mall, a scenic park great for ice-skating, sledding. In the summer, it plays host to a variety of community events.

The nearby Maudslay State Park combines history with the outdoors.

It features 19th-century gardens, walking trails, meadows, bridges, ponds, and stone arch bridges. In the winter, you might also be lucky enough to spot a bald eagle here.

A whale's tail in the water near Gloucester MA
Embark on a whale watching cruise from Gloucester, a fishing town in Massachusetts.

Gloucester

Drive time from Boston to Gloucester: 53 minutes

The seaside town of Gloucester makes for a solid weekend getaway from Boston, offering an exciting array of things to do.

Gloucester is about an hour away from downtown Boston. 

Did you know that you can see humpback whales off the coast of Cape Ann?

The North Atlantic coast is one of the top five whale sighting destinations in the world according to WWF!

Experience the beauty of this region, and increase your chances of spotting these incredible mammals on a whale watching tour from Gloucester.

If chasing lighthouses is on your agenda, head to the iconic Eastern Point Lighthouse or Dog Bar Lighthouse.

Beach hoppers can choose between Good Harbor Beach for white sand and fantastic waves and Wingaersheek Beach for its calm, crystal clear waters and soft sand.

You could also head for a sunset schooner cruise for a unique experience on the water. 

For a short hiking adventure, walk to Rafe’s Chasm for clifftop views.

Seafood lovers have good reason to rejoice in Gloucester. Many local fishmongers provide fresh lobsters, cod, or tuna. Further, oysters are a specialty in the area too. 

For an offbeat excursion, head to Hammond Castle Museum, located by the coast, to see an impressive collection of owner John Hays Hammond Jr.’s medieval artifacts. 

A photo of people on Old Silver Beach in Cape Cod Falmouth
Cape Cod is a hot favorite weekend getaway in Massachusetts

Falmouth, Cape Cod

Drive time from Boston to Falmouth: 1 hour 45 minutes

A popular summer getaway in Cape Cod, Falmouth is home to eight quaint villages and miles of beautiful coastline.

Falmouth is 80 miles south of Boston, though traffic to the town can be notorious during peak summer months. 

Begin your weekend in Cape with a visit to Old Silver Beach, located in North Falmouth.

Parking is available, though it is best to get here early as it is a well-known beach.

For a quieter beach, try heading to Wood Neck Beach. For sunsets, Chapoquoit Beach in West Falmouth is a great bet. 

In the afternoon, stroll through the vibrant Main Street, where you will find restaurants, bakeries, and souvenir shops.

For kids, there’s candlepin bowling, a candy store, and delicious ice cream too.

Another fun activity to pursue in Falmouth is biking down the 10-mile long Shining Sea Bikeway that stretches from Falmouth to the scenic Woods Hole town in the south.

Built on an old railroad line surrounded by flowers and trees, the route also crisscrosses through the Salt Pond Bird Sanctuary. 

A visit to Cape Cod is incomplete without seeing a lighthouse.

Visit the Nobska lighthouse at the far end of East Falmouth. In the summer, you can also take a tour of the tower.

Conclude your stay with a visit to Woods Hole, where there are restaurants, a free aquarium, and a Science Discovery Center. 

A photo of autumn colors by a lake in Stockbridge, MA
Stockbridge, Berkshires makes for an ideal romantic getaway in the fall.

Stockbridge, Berkshires

Drive time from Boston to Stockbridge Berkshires: 2 hours 20 minutes

Only a 2-hour drive away, the Berkshires region in Western Massachusetts is a favorite getaway for Bostonians.

While there are several lovely towns in Berkshires, Stockbridge, MA makes for an ideal weekend getaway since it is right off the Mass Pike.

It is a walking-friendly town that’s lively all year round. 

There’s much to do in this town, starting with the Norman Rockwell Museum, which includes original works of the distinguished American illustrator Norman Rockwell. 

Next, make your way to The Mount, a historic estate designed by Edith Wharton in 1902.

The property includes a 19th-century main house, Italian gardens, and stables. Season permitting, you could have lunch at their terrace cafe too. 

If you enjoy hikes, walk the beautiful and comfortable Mary V. Flynn trail to be surrounded by birch trees, pines, and cottonwoods.

For a more strenuous adventure opt for Laura’s Tower Trail for stunning views from a summit. 

In the spring, summer or fall, be sure to pop into either Berkshire Botanical Gardens or Naumkeag, another historical estate with expansive gardens and trails, to see flowers in bloom. 

While you’re in Stockbridge, book a stay or a meal at the boutique hotel Red Lion Inn. It is a landmark in the area and an excellent choice for a romantic weekend. 

Read More: 20+ Top Things to do in the Berkshires

Golden sand on Race Point Beach Cape Cod MA
Race Point Beach in Provincetown, MA

Provincetown

Drive time from Boston to Provincetown: 2 hours 25 minutes

Located at the northernmost tip of Cape Cod, P-town, or Provincetown is an all-around family-friendly travel destination.

Surrounded by forty miles of stunning beaches, a lively main street, a thriving arts scene, and notable lighthouses, there’s never a dull moment in this LGBTQ-friendly town.

You could either drive 2.5 hours to reach Provincetown from Boston or take a 90-minute ferry from the city.

Ferries to P-town are operational between spring to fall.

Start with a visit to Race Point Beach and Lighthouse.

For incredible sunset views, head to the Herring Cove Beach in the evening with a bottle of bubbly and a picnic hamper. 

Other breathtaking beaches to visit in the area are the Head of the Meadow Beach in nearby Truro and the Cahoon Hollow Beach and Marconi Beach in Wellfleet. 

The hundred-year-old Pilgrim Monument, commemorating the Mayflower Pilgrims, provides 360-degree views of the entire town.

There is an entry fee of $18/adults to climb atop this 252-foot monument.

The six-mile-long Cape Cod Provincelands bike trail is another scenic challenge that many bikers enjoy.

The trail passes through cranberry bogs, marshes, and exposed dunes. Both Race Point and Herring Cove beaches have access to the trail too. 

Commercial Street in downtown P-town is a hub for art galleries, cafes, restaurants, bars, and some interesting souvenir shops. 

Sweeping views of Atlantic Ocean from the Aquinnah Cliffs in Martha's Vineyard
Beautiful panoramic views from Aquinnah Cliffs in Martha’s Vineyard

Martha’s Vineyard

Travel time from Boston to Martha’s Vineyard: 2 hours 35 minutes

The wondrous island of Martha’s Vineyard is a tempting summer getaway for New Englanders, being only 45 minutes away from Woods Hole, MA by ferry.

The island is located south of Massachusetts and also has a small domestic airport.

One of the best things to do in Martha’s Vineyard is to visit the Aquinnah Cliffs for beautiful panoramic views. These multicolored cliffs formed by glaciers are a national landmark.

You won’t miss the famous Gay Head Lighthouse while you are here. You could also tour the lighthouse for $5 between May-September. 

If you’re a beach lover, head to Oak Bluffs Town Beach for calm waters, the Joseph A. Sylvia State Beach for swimming and sunbathing, or South Beach for surfing.

Short on time? Pick from one of these small group island tours to make the most out of your time in Martha’s Vineyard!

The 500-acre Cape Poge Wildlife Refuge on the adjacent island of Chappaquiddick is accessible via the 5 minutes long Chappy Ferry in Edgartown.

Here you can see an expansive shoreline and a historic lighthouse, and indulge in birdwatching and seaside explorations. 

Culture lovers will enjoy the colorful gingerbread houses and the Flying Horse Carousel in Oak Bluffs. The latter has original hand-crafted horses from 1875. 

Sunset lover? Make your way to the beach in the small fishing village of Menemsha. Grab some pizza along the way from the General Store in Chilmark. 

Martha’s Vineyard Gourmet Cafe & Bakery is a must-visit in Oak Bluffs for late-night donuts.

Aside from that, there are several stores, cafes, and restaurants in Oak Bluffs and Edgartown for those who enjoy retail therapy. 

The striped Sankaty Lighthouse in Nantucket
A hike on Sconset Bluff ends at the stunning Sankaty Lighthouse in Nantucket, MA

Nantucket

Travel time from Boston to Nantucket: 2 hour 45 minutes

Nantucket is a beautiful island off the southern coast of Massachusetts. It is a summer favorite for the who’s who in New England!

To get to the island, hop on an hour-long ferry from Hyannis in Cape Cod, MA. 

Cobblestoned streets, dune-backed beaches, postcard-worthy views, and stunning lighthouses will welcome you to Nantucket.

The island also has a small airport and is walking and bike-friendly.

Shuttle buses run throughout the island, making it convenient to explore the beaches without renting a car. 

If you visit in the summer and beaches are on your agenda, then you’re in luck!

For gentle surfside beaches head to Jetties Beach, Steps Beach, Children’s Beach, or Brant Point Beach, close to the Brant Point Lighthouse.

The beaches on the south shore like Cisco, Surfside, and Madequecham have stronger surf and cooler water.

Take a bus to Sconset on the southeastern edge of the island and stroll through Sconset Bluff for marvelous views of the coastline.

This 2-mile scenic public walkway behind lavish homes with picturesque gardens eventually leads to the striped Sankaty Lighthouse on Baxter Road. The walk begins in the town of Sconset.

To learn about Nantucket’s whaling history visit the island’s Whaling Museum.

The museum has a 46-foot sperm whale skeleton, an observation deck, and a candle factory. 

There are several boutiques, restaurants, souvenir shops, and cafes in and around Main Street in Nantucket.

To try local brews, head to Cisco Brewery.

For a fancy meal, reserve a table at Proprietors. Nantucket Resort Collection, in the island’s Old Town, is a fabulous boutique hotel to base yourself out of. 

Maine (ME)

fall foliage near Kennebunkport Maine
Beautiful fall foliage near Kennebunkport, Maine

Kennebunkport

Drive time from Boston to Kennebunkport ME: 1 hour 30 minutes

The delightful town of Kennebunkport is a beach lover’s paradise in the summer months.

It is one of the best places to visit in Maine!

It is also one of America’s favorite Christmas towns, and there are many ongoing activities, markets, and events held in the area throughout December. 

Fortune’s Rock Beach, Colony Beach, and Gooch’s Rock Beach are some of the most popular coastal beaches to visit in Kennebunkport.

Here, you can also satiate your hunger for adventure with stand-up paddle boarding, kayaking, or surfing. 

The Seashore Trolley Museum is an all-around fun place for kids and adults alike between May-December.

If you have a vintage car lover, head to the Maine Classic Car Museum. 

History lovers can take a self-guided walking tour through Kennebunk’s Museum in the Streets to look at 25 panels that include rare photographs, documents, and records of the town’s history.

If you enjoy fine dining, reserve a table at Earth at the Hidden Pond or Bandaloop. Both restaurants have a wholesome focus on locally sourced produce. 

The Kennebunkport Inn, which used to be a historic mansion, and the elegant Breakwater Inn & Spa are two notable hotels in the vicinity. 

A view of Portland lighthouse and fall colors in Maine
Visiting the Portland lighthouse is a must-do activity in Maine!

Portland 

Drive time from Boston to Portland ME: 1 hour 45 minutes

Portland, Maine, is the place to head to if you enjoy outdoor adventures, history, culinary, arts, and breweries!

Touted as Boston’s hip neighbor, Portland provides a leisurely break from the city. 

Before you make your way to downtown Portland, plan a visit to see Portland Head Light for postcard-worthy views of the Atlantic Ocean.

Another beautiful lighthouse to visit during sunset is the Victorian-style Bug Lighthouse located in southern Portland.

An engaging tour is an ideal way to get introduced to Portland and its culture! This 3-hour tour of Portland led by a local historian and guide is a great option for those who want to learn about the lesser known gems of the city!

For a slice of history, head to Portland’s West End neighborhood. Here, you can walk through streets with preserved Victorian homes with lush private gardens.

You could also take a tour at Victoria Mansion, which is open all year round. 

Portland’s Old Port district is the perfect blend of the past and present. It is a working waterfront dotted with restaurants, bars, and boutiques. 

It’s also the ideal spot to taste Maine inspired cuisine! This culinary walking tour of Old Port takes you to seven eateries and is a great way to kickstart your stay in the city.

Art lovers should make their way to the Portland Museum of Art to see their excellent collection of period and modern artworks. 

Portland Observatory is another must-visit landmark in the city. 

Culinary lovers have good reason to rejoice in Portland. From delicious donuts made from Maine potatoes, at the famed The Holy Donut, to seasonal brews from Allagash and Geary Brewing Co., pioneers from the craft beer boom – there’s much to savor!

Seafood lovers will find fresh lobsters galore, and the choices in fine dining, casual cuisine, and even ethnic eats are diverse! 

A panoramic view of the Atlantic Ocean and surrounding areas from Camden Hills State Park Maine
Plan a picnic at Mt. Battie in Camden Hills State Park, Maine

Camden

Drive time from Boston to Camden ME: 3 hours 20 minutes

Located in the heart of midcoast Maine, Camden is a picturesque seaside town where mountains meet the sea.

Camden’s biggest outdoor attraction is Camden Hills State Park. On sunny and clear days, it is possible to see Acadia National Park’s Cadillac Mountains from here.

While you’re in the park, hike the fairly easy 1.5-mile trail to Mt. Battie for expansive views of the Atlantic Ocean and surrounding islands. This is a great spot for a picnic too. 

Next, dip your feet in the water at Laite Memorial Beach or head to locally known Barrett’s Cove at Megunticook Lake for lesser crowds and spectacular views.

Alternatively, Camden Harbor is an ideal place to take a windjammer cruise or a lobstering cruise. Admire the rugged beauty of Maine’s coastline on a 2-hour windjammer sunset cruise! Camden also plays host to a Windjammer Festival over Labor Day. 

For gardens and interpretative trails, head to Merryspring Nature Center.

The dining scene in Camden and nearby Rockport has been making waves too.

Natalie’s for American fine dining, Long Grain for eclectic Asian food, Primo for farm to table, and Nina June Restaurant for Italian Mediterranean cuisine are worth checking out!

Sunflowers blooming against the landscape in Mohnegan Island Maine
Monhegan Island in Maine is an underrated weekend getaway from Boston

Monhegan Island

Travel time from Boston to Monhegan Island: 4 hours 30 minutes

Looking for a quiet weekend escape? The small island of Monhegan accessible only by a 60-minute boat from the coast of Maine may be just what you need. 

Park your car at Port Clyde, New Harbor, or Boothbay Harbor in central Maine, and take a ferry to Monhegan between spring and fall.

The island is said to be one of the first that was visited by Portuguese and Basque fishermen. Naturally, fishing, along with tourism are the island’s mainstays. 

Here, you can enjoy unmatched panoramic cliffside views of the surrounding Atlantic Ocean.

There are 9 miles of natural trails through forestlands, meadows, coves, and ledges. 

You can see harbor seals on the Duck Rocks near Pebble Beach. Birdwatchers will be delighted to see migratory birds too. 

For a small island, Monhegan has a bunch of options for dining and drinking.

Take your pick for a meal at Monhegan Fish House, Monhegan House Dining, The Barnacle, or The Novelty. Locally roasted coffee is available at Monhegan Coffee Roasters.

Shopping enthusiasts will be surprised to see a small gift store called The Black Duck, with its collection of eclectic goodies. 

The island also has a mini arts community whose works are displayed in the few art galleries in the town side of the island. 

There are a few inns, rentals, and guesthouses on the island. The Island Inn and Monhegan House are top choices. 

New Hampshire (NH)

Portsmouth Skyline on Piscataqua River
Portsmouth’s proximity makes it one of the popular weekend getaways from Boston

Portsmouth

Drive time from Boston to Portsmouth NH: 1 hour

The once historical seaport town of Portsmouth is today a vibrant New England city with restaurants, boutiques with a unique culture, and several outdoor activities. 

Being only an hour away from Boston, this walkable city is a great last-minute getaway. 

For a charming view of the Portsmouth Harbor Lighthouse, head to the Great Island Commons in New Castle.

The lighthouse looks particularly beautiful against the backdrop of the gorgeous Atlantic blue waters. There is a pavilion, picnic tables, and a playground too.

Strawberry Banke Museum, a 10-acre outdoor history museum, brings almost 300+ years of American history alive with its historic homes, gardens, costumed role players, and traditional crafts.

It’s a great choice for a family-friendly outing in Portsmouth. In the winter, the museum has an outdoor ice skating rink for skating enthusiasts. 

Hampton Beach, one of New England’s most visited beaches, is 20 minutes south of downtown Portsmouth.

The beach town has a variety of entertainment options for the entire family, including arcades, mini-golfing, and restaurants.

For a pleasant stroll in downtown Portsmouth, head to the waterfront Prescott Park.

Foodies will be delighted to find a variety of restaurants, breweries, and cafes in the city too. 

The Hotel Portsmouth is a solid choice for a stay in the heart of the town.

Lake Winnupesaukee in New Hampshire is another easy to reach weekend getaways from Boston
Get out on the water in Lake Winnipesaukee, New Hampshire

Lake Winnipesaukee

Drive time from Boston to Lake Winnipesaukee NH: 2 hours

New Hampshire has several lakes and one of the most well-known among them is Lake Winnepisaukee.

Surrounded by mountains and located at the foothills of the majestic White Mountains, the lake provides countless opportunities for activities and outdoor adventures.

For incredible views of the lake, jumpstart your visit with a hike to the top of Mount Major.

There are multiple intermediate trails to the top of the summit, but you would be rewarded with spectacular views of the lake and the surroundings. 

For a lighter, albeit equally picturesque experience, visit the Castle in the Clouds.

This 16 room mansion, open seasonally, offers tours of the estate and has several scenic trails for guests to wander around. From here, you can also catch wonderful views of Lake Winnepesaukee.

For a relaxing day by the waters in the summer, head to Ellacoya State Park or park yourself inside Wentworth State Park. 

No visit to Lake Winnipsaukee is complete without getting on a boat!

You could rent a boat or take a cruise too. Other popular activities in the area include fishing, snowmobiling, skiing, and iceboating.

If you’re visiting in the fall season, take a road trip around the lake from Meredith to Wolfeboro and Sanbornville. You could also extend your trip to Conway in the north. 

To explore Lake Winnipesaukee, it is ideal to base yourself out of the towns of Meredith, Laconia, Center Harbor, or Moultonborough.

Drone views of fall foliage in White Mountains, New Hampshire
New Hampshire makes for one of the best weekend trips from Boston, especially in autumn.

North Conway

Drive time from Boston to North Conway NH: 2 hours 35 minutes

Surrounded by the scenic White Mountains, North Conway, New Hampshire is the gateway to an array of outdoor recreational sights in the area. 

Start your trip by driving thirty minutes north to the top of the tallest peak in the North East, Mt. Washington.

This is an area with one of the most unpredictable and windiest weather conditions.

In the summer or fall, you could drive the Auto Road or take a Cog train to experience the beauty of peaks amidst colorful foliage.

In the winters, guided snow coach tours are offered for those looking for an unforgettable snowy adventure.

A must do activity, especially in summer and fall is a road trip through Kancamagus Highway, forty minutes west of North Conway.

This 35-mile scenic drive along New Hampshire’s Rt. 112 is a designated American Scenic Byway. Pack a picnic lunch as there are no restaurants or gas stations along the way.

Sabbady Falls, Rocky Gorge are some of the noteworthy stops along the way. 

For a journey back in time, experience a train ride on a restored vintage locomotive starting at the 1874 Victorian station in North Conway Village.

Train rides range from 1-5.5 hours and provide an exclusive view of the vivid landscape. 

Diana’s Bath, a gushing waterfall, is another year-round attraction in North Conway.

This 75-foot waterfall is a family favorite in the summers with several rocks, ledges, pools to explore. The .6 mile graveled path to the falls is flat and fairly accessible. 

Not too far away, Echo Lake State Park is a popular place for hiking, swimming, kayaking, picnicking, and rock climbing. 

Vermont (VT)

A red barn and fall colors over Jenne Farm near Woodstock Vermont
Fall colors across Jenne Farm in Woodstock, Vermont. The latter is a great weekend getaway in New England

Woodstock

Drive time from Boston to Woodstock VT: 2 hours 15 minutes

To escape to an idyllic small town village, head to Woodstock in northwest Vermont. 

Be sure to start your visit in the town center. Central and Elm Streets in particular have several family-owned boutiques. 

The newly created Ottauquechee River Trail starts from the town and provides travelers with beautiful views of Mt. Peg and Mt. Tom. 

Woodstock is a hub of farm to table.

There are many working farms, maple sugar houses, and cheesemakers in the area that offer tours, treats, and even accommodations in their working farms. 

For an authentic Vermont farm experience, head to Billings Museum & Farm in Woodstock.

The museum offers daily programs, activities, and events for all age groups. Kids will particularly enjoy the sunflower house and gardens.

While you’re here, don’t forget to sample their raw-milk cheddar cheese. 

Woodstock and its surrounding areas are dazzling in the fall.

If you enjoy backroads and quaint farms drive to Sleepy Hollow Farm in Pomfret or Jenne Farm in Reading to snap that perfect fall photograph. 

You are sure to also find several photo-worthy spots along the way to Pomfret, Barnard, and Bridgewater.

Some Instagram-worthy covered bridges include Taftsville, Middle Bridge. The Quechee Covered Bridge in Quechee is another much-loved spot. 

Woodstock’s 506 On The River Inn is a charming family friendly stay option in the area.

Gondolas surrounded by colorful trees in Stowe Vermont
Stowe, Vermont is one of the best fall weekend getaways in New England

Stowe

Drive time from Boston to Stowe VT: 3 hours

Surround yourself in picturesque scenery, a relaxed pace, and friendly faces in Stowe, a tourist favorite in the northern part of Vermont. 

Stowe is a town for all four seasons.

It is a popular ski town in the winters, a maple sugaring hot spot in the spring, a family-friendly destination in the summer, and a must-stop for leaf peepers in the fall. 

The nearby Mt. Mansfield, Vermont’s tallest peak, is best seen through a hike if you are visiting between April-October. 

From the town, take a leisurely 0.1 mile walk up to Sunset Rock for a panoramic view of historic Main Street and then head up to the Upper Overlook to see Mt. Mansfield on their west.

The 4.9 miles historic Long Trail to the summit is for the most adventurous!

If you prefer to skip the walking, drive up the Auto Toll Road to the summit or enjoy the scenic views atop Stowe’s Gondola SkyRide.

Stowe is a winter sports lover’s playground.

Pick from snowmobiling, sledding, skiing, skating, sleigh rides, snowshoeing, or wind down at one of the luxury wellness resorts in the area. 

Summer is when Stowe truly comes alive.

You could walk or bike through the Stowe Recreation Path, go for a dip at Waterbury Reservoir or Lake Elmore, or plan a picnic and see one of the many waterfalls in the area.

Stunning fall foliage awaits you if you choose to visit Stowe in late September or October.

Drive through backroads, hike a trail for a bird’s eye view of the colors, and lose yourself in the magic of autumn.

There are many covered bridges in the area that look beautiful surrounded by fall colors.

If you’re a craft beer connoisseur, a brewery tour could be right up your alley! The tour will take you to four breweries in the area, and you’ll also learn a lot about Stowe in the process!

While you’re in the town, walk around Main Street and enjoy the pleasant vibe. 

A photo of the Hildene Estate with gardens in the foreground
The Hildene Estate in Manchester, Vermont, is the summer home of the Lincoln family

Manchester

Drive time from Boston to Manchester VT: 3 hours 10 minutes

The quaint mountain town of Manchester, Vermont is home to stunning scenery and numerous outdoor adventures. 

For fascinating panoramic views, take an unforgettable drive up to the summit of Mount Equinox, the tallest peak in the Taconic Range.

This road is open from May 31-October 31.

There are several picnic areas on the route and you will see beautiful scenery all around. The tickets for a car and driver are $20, and $5 for every passenger, free for kids under 10.

The Hildene Estate, the summer home of the Lincoln family, is another popular attraction in Manchester.

At the estate, you can take a self-guided tour of the home, listen to the 1,000-pipe Aeolian organ and see the Formal Garden.

There are walking trails, a Hildene Farm goat dairy and cheese-making facility, and exhibits.

Entry costs $23/adults and $6 for 6-16-year-olds. 

If you’re a nature and art enthusiast, head to Southern Vermont Arts Center for incredible sculptures in an outdoor space.

The center has rotating exhibits and storytelling trails.

They also have a small restaurant, gift store, studio classrooms, outdoor classrooms, and large in-door performance building.

Stop by at Depot 62 for a delicious Turkish-Mediterranean feast. 

Shopaholics will be delighted to see outlet stores of several high-end brands, alongside boutique stores in the town. 

a view of Church Street in Burlington Vermont
Burlington, Vermont is an ideal fall weekend getaway in North East

Burlington

Drive time from Boston to Burlington VT: 3 hours 15 minutes

The lively town of Burlington is located in northern Vermont, on a hillside by the shores of Lake Champlain.

The town is known for its whimsical arts, crafts, and culture scene. 

Begin your visit to Burlington at Church Street Marketplace, which is thriving all year round.

Here you will find boutiques, art galleries, cafes, restaurants alongside branded stores.

Street performers, outdoor pop-ups, and vendors keep the venue buzzing too. 

For unmatched sunset views, take a sightseeing cruise on Lake Champlain with the Spirit of Ethan Allen Cruises.

Cruises are offered between May-October. Relax on the water, order from a dinner menu, and soak in the magical atmosphere. 

For a dose of art, head to Robert Hull Fleming Museum of Art.

The Museum features collections of 20,000+ pieces covering American, African, European, Ancient Egyptian, and Middle Eastern art, and work by Vermont artists.

In the summer, grab some bikes or a kayak and head over to Lake Champlain Islands.

These islands are connected to Burlington by causeways and bridges and make for a great day trip.

You could also relax on Waterfront Park or Battery Park in town. 

Not far away is Shelburne Farms, a working farm and nonprofit that offers programs on sustainability. It is a beautiful farm with outdoor trails, barns, a bakery, and gardens. 

Perhaps the best way to experience the vibe of Burlington is through a visit to its Farmer’s Market.

Held on Saturdays in the summer, it is the perfect way to sample local produce and pick up specialty crafts. 

Rhode Island (RI)

The Providence skyline in Rhode Island
Providence, Rhode Island is one of the most easy to reach getaways from Boston

Providence

Drive time from Boston to Providence RI: 58 minutes

An easy getaway from Boston, Providence is a family-friendly town offering an assortment of attractions for the weekend traveler. 

Start your stay by visiting the Rhode Island School of Design Museum.

Featuring a wide variety of 10,000+ art objects, the Museum is sure to impress any art lover.

Highlights include original artwork by Van Gogh, Picasso, and Monet. Entry to the museum is free on Thursday, Friday evenings, and Sundays. 

If you’re traveling with kids, plan a visit to the Roger Williams Park Zoo.

Here you can find an African elephant, a Masai giraffe, zebras, a red panda, a snow leopard, and many more animals in their natural setting. 

On a sunny day, make your way to the 427-acre Roger Williams Park for a picnic, a walk, or a bike ride. There is a carousel in the park as well.

Other attractions in the park include the Temple of Music, the Rose Garden & the Japanese Garden. 

Between May-October, the WaterFire festival, held several times during the week, is a huge draw for visitors.

This art phenomenon is held on a river, and there are several other festivities, street vendors, and food trucks nearby. Book a gondola ride on the river to make the most of the event. 

To support the local economy and buy local, head to the popular Providence Flea, for artisan and vintage products. 

The breakers mansion in Newport, Rhode Island
Take a cliff walk in Newport and admire mansions like The Breakers.

Newport

Drive time from Boston to Newport RI: 1 hour 25 minutes

For a classic coastal getaway from Boston, head to Newport, most known for its extraordinary mansions.

When it comes to things to do, there are several possibilities in this town, located on Aquidneck Island in Narragansett Bay.

Newport’s Gilded Age mansions are located on cliffs on the town’s shoreline.

Take a self-guided 3.5-mile walking tour to see these summer homes of America’s wealthiest as you admire the dramatic scenery around you.

You can also opt for a paid tour to see some of these gorgeous homes from inside.

The Breakers, Marble House, and The Rosecliff are among the most famous Newport mansions.

Love scenic road trips? The 10-mile Ocean Drive starting at historic Bellevue Avenue could be for you.

Stop at Brenton Point State Park midway on this drive to see spectacular views of the East Coast. This is the location where Narragansett Bay meets the Atlantic Ocean. 

Reserve a sunny day for the beach. Easton’s Beach and First Beach are among the most beautiful in the country. 

A visit to Fort Adams State Park is another must-do in Newport.

Located at Newport Harbor, this is the biggest Fort in America. While you could do a self-guided tour, a guided tour of the premises is a great way to experience history. Entry is $7/adults and $4/children. 

Downtown Newport is where all the action is!

You will find cobblestone paths between Bowen’s and Bannister’s Wharves and that’s where all the boutiques and restaurants are located.

Newport is also known for its vineyards and breweries.

Stairs leading down to the beach in Block Island, Rhode Island
Block Island, one of the lesser explored Boston weekend getaways, is home to unspoiled beaches

Block Island

Travel time from Boston to Block Island RI: 2 – 2.5 hours

Unspoiled white sand beaches and stunning natural beauty await you at Block Island.

The best way to get to Block Island is via a ferry from Narragansett town, Rhode Island. Ferries are also available from Newport. 

For a relaxing day of sun and sand, hit up one of the beautiful beaches on the island.

Crescent Beach and Baby Beach have calm waters, lifeguards, amenities and are popular for family picnics.

For outstanding cliffside scenery, visit Mohegan Bluffs and the beach below the cliffs. If you enjoy waves, head to Mansion Beach. 

No visit to Block Island is complete without a visit to one of its two historic lighthouses.

The South East Lighthouse is located on Mohegan Bluffs and a visit to this spot can be combined with a beach day. The Block Island North Lighthouse is located further north.

At the Block Island Nature Conservancy, you can access 25 miles of walking trails.

The trails provide a rare opportunity to witness migratory birds in the spring and fall, along with the island’s diverse scenery. There are also separate dedicated trails for biking. 

The Clay Head Nature Trail is another beautiful 2-mile hiking path that spirals through meadows and clay bluffs overlooking the ocean.

Culture and curio lovers will be delighted to find art galleries and gift shops on the island, offering unique souvenirs with a flavor of the island.

In the summer, plan your visit to include some time at the Block Island Summer Farmer’s Market!

Connecticut (CT)

Connecticut's red colored West Cornwall Covered Bridge surrounded by peak fall colors.
Go to Connecticut’s West Cornwall Covered Bridge for postcard worthy views in the fall.

Litchfield Hills

Drive time from Boston to Litchfield Hills CT: 2 hours 25 minutes

Surround yourself in rural landscapes, rolling hills, and charming towns in Litchfield Hills, Connecticut.

With brilliant connectivity to Boston and Manhattan, the area is ideal for taking a break from busy city life. 

If you enjoy hiking, you’re in luck.

A part of the Appalachian Trail runs through Litchfield County.

To see a scenic part of the Appalachian Trail, take the Bull’s Covered Bridge River Walk. The 4.5-mile loop features views of waterfalls and gorges on the Housatonic River. 

The nearby Macedonia Brook State Park has a network of trails for all levels of hikers.

Not too far away, Kent Falls State Park offers an easy waterfall hike too.

You could also opt to visit Mt. Tom State Park for a light hike to the top of a stone tower for impressive scenery.

New England is famous for its covered bridges and the 242 feet long West Cornwall Covered Bridge is one of Connecticut’s beautiful gems worthy of a visit. 

For a family-friendly adventure on the waters, head to Lake Waramaug and rent canoes.

The beautiful Housatonic River offers opportunities for rafting or kayaking too. 

The Litchfield Hills makes for a fantastic getaway in the fall and one of the best ways to experience the quiet countryside is by driving around the backroads in October-November.

The routes around Kent, New Preston, and Lake Waramaug are particularly dazzling. 

Antique lovers will enjoy a visit to Mill House Antiques in Woodbury. There is also a small upscale shopping district in New Preston. 

While in the region, don’t miss out on the supremely delicious ice cream from Arethusa Dairy available at their shop in Bantam.

You could also visit their dairy farm in Litchfield to stock up on yogurt, milk, and cheese.

A beluga whale in Mystic aquarium
The beluga whales attract many visitors to Mystic Aquarium each year.

Mystic

Drive time from Boston to Mystic CT: 1 hour 45 minutes

The waterside village of Mystic has something for every age group.

If you enjoy nature, museums, art, shopping, and a vibrant dining scene, this is the place for you.

Start your weekend with a visit to Mystic Seaport, Mystic’s riverfront museum, the country’s largest maritime museum.

In this indoor-outdoor museum, you can experience life in a 19th-century seafaring village, see the museum’s collection of preserved ships, explore exhibit halls, a vintage garden, a children’s museum, and even take a cruise on a historic boat. 

The Mystic Aquarium also draws a large number of visitors each year.

The aquarium is home to New England’s only beluga whales located close to the entrance. Inside, you can see 300+ species, including several jellyfishes, sharks, stingrays among others. 

Just across the street from the Aquarium is the Old Mystick Village, an outdoor venue in a village setting.

Here you can browse through stores and gourmet shops, or enjoy a cone from Mango’s Homemade Icecream shop while you people watch.

On a sunny day, head out for a coastal walking trail inside Bluff Point State Park located near Groton.

There’s an old carriage road leading to Bluff Point that also provides views of islands and New London Ledge Light.

Downtown Mystic is abuzz with shops, bakeries, and boutiques.

Don’t miss the seafood at Red 36 and stop by at Sift to indulge in French pastries.

In nearby Stonington, you will find breweries and vineyards too. 

A sign for Frank Pepe's pizza in New Haven
New Haven is known to have America’s best pizzas!

New Haven

Drive time from Boston to New Haven CT: 2 hours 15 minutes

New Haven is a historic town with a contemporary vibe.

Best known for having the most delicious pizzas in America and one of the topmost Ivy league universities in the country, it makes for a promising weekend vacation from Boston. 

The world-renowned Yale University is located in New Haven. Founded in 1701, the sprawling institute is spread across the town.

Take a self-guided tour of the campus to see mid-century brownstone buildings. Or, check in with the Yale Visitor Center for a schedule of free tours. The university is particularly beautiful in the fall. 

The Sterling Library, designed to resemble a gothic cathedral is a must-see at Yale.

Also be sure to make time for Yale’s Art Gallery, Peabody Museum of Natural History, the Center for British Art, and the Collection of Musical Instruments. 

The Beinecke Rare Book and Manuscript Library is devoted to rare books and has a copy of the Gutenberg Bible on permanent display. 

All that walking will hopefully build up your appetite.

Queue up, if you have to, for a table at one of the many Connecticut culinary institutions in Little Italy.

Plan a visit to Frank Pepe’s Pizzeria Napoletana best known for its delicious brick fire oven pizzas or Sally’s apizza for their crispy crusts. 

New Haven also has a thriving theatre scene.

You can catch one of the regular performances held at the Shubert Theater or the Long Wharf Theatre. 

The town’s Chapel Historic District is known for its shops, art galleries, museums and is an ideal neighborhood for a stroll. 

Here, you could stay at The Study, a sophisticated and relaxed boutique hotel, minutes away from the Yale University’s Arts Campus.

New York

Hudson river, a bridge and mountains around Hudson Valley
Hudson Valley is among the best weekend getaways for couples.

Hudson Valley

Drive time from Boston to Hudson Valley NY: 3 hours 20 minutes

If you’re looking for a retreat steeped in design, art, culture, that also offers outdoor adventures, farm-to-table meals, and wineries, look no further than Hudson Valley in New York state.

Kickstart your weekend with a visit to Opus 40 in Saugerties, a sprawling 50-acre environmental sculpture park built entirely by hand using traditional tools.

The park has sculptures, meadows, a gallery, a museum, and a sitting area.

For stunning 360-views of the Hudson River, visit The Walkway Over the Hudson, a 1.2-mile long accessible biker and pedestrian-friendly bridge that connects the towns of Poughkeepsie and Highland.

The bridge provides especially beautiful panoramic views during the fall.

In the summer or fall, grab a picnic basket and head to Storm King Art Center, an open-air museum with a large collection of contemporary sculptures.

A great way to explore this sprawling museum is by biking around!

For unmatched views of the countryside, drive through sections of the Shawangunk Mountains Scenic Byway to see stunning fall foliage.

With 18 state parks, a state forest, and several outdoor sites, there is no dearth of outdoor activities in Hudson Valley. The region also has a vibrant dining scene.

Kingston, New Paltz, Woodstock, and Saugerties are some of the popular towns in the area.

Yellow taxis, lights and hoardings in New York City
Looking for weekend trips from Boston without a car? New York City is a solid choice!

New York City

Drive time from Boston to New York City NY: 3 hours

The iconic city of New York makes for an exciting getaway from Boston. With its parks, museums, restaurants, and landmark buildings, it offers all elements you would need for an active city break. 

Begin your visit to this wondrous city with a visit to Central Park.

This 843-acre urban park located between the Upper East Side and Upper West Side of Manhattan is world-famous. 

In the spring, you can see cherry blossoms in bloom near Central Park’s Cherry Hill, Pilgrim Hill, and Shakespeare Garden.

Set against the backdrop of skyscrapers, Sheep Meadow is a lush spot for a picnic in the summer. I

ndulge in a horse carriage ride or rent a boat from Loeb Boathouse and go boating while enjoying views of Bethesda Terrace and Bow Bridge. Biking is another great way to explore this massive park. 

Families will enjoy visiting Umpire Rock, the Butterfly Conservatory, Heckscher Playground, the Central Park Zoo, and Natural History Museum. 

One of the best ways to experience the grandeur of the skyscrapers in New York City is through a visit to an observation deck.

Head over to the 86th-floor observatory of the Empire State Building for classic views of the city. 

For a unique perspective of New York City, visit Highline, a public park built on an elevated rail line.

Stroll through the pathway as you encounter gardens, art, performances, food stalls, and a distinctive view of the neighborhoods around.

If you’re a museum lover, you’re in for a treat. New York City has several interesting museums.

If you enjoy art, pick between the Museum of Modern Art, Metropolitan Museum of Art, or Whitney Museum of American Art. 

Architecture and culture lovers would enjoy photographing the Flatiron Building, and strolling through the New York Public Library. 

In the evening, head over to see the lights and glamor of Times Square.

Watching a Broadway show in the city is an ideal way to round up your visit. 

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