10 Fabulous Things to do in Lenox MA

Nestled between the towns of Pittsfield and Stockbridge, Lenox Massachusetts is a charming small town in the Berkshires. 

Besides being the summer home of the Boston Symphony Orchestra, the town has attracted several notable authors, artists, and industrialists, all of whom have left their impression on the surroundings.

Whether you’re visiting solo, with your family, or as a couple, there are several exciting things to do in Lenox MA. 

Here’s a handy list to help you get started. 

TABLE OF CONTENTS
Things to do in Lenox MA
Hotels in Lenox Massachusetts
Tanglewood Festival is one of the best things to do in Lenox MA - this is grounds of the festival venue during fall.
Watching a live concert at The Tanglewood Music Festival is one of the best things to do in Lenox MA. Photo: Shutterstock|Joseph Sohn

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Lenox MA Things to do

Enjoy an outdoor concert with a picnic at the Tanglewood Music Festival

Back in 1936, the Boston Symphony Orchestra gave its first outdoor performance at Holmwoods, in the Berkshires region.

The same year, they received a donation of Tanglewood, the Tappan family estate, with its buildings and 210 acres of lawns and meadows, which enabled them to start the Tanglewood Music Festival in 1937.

Today, the festival welcomes over 3,50,000 music lovers to its venue each summer. 

Aside from the Boston Symphony Orchestra, the Boston Pops and several classical, contemporary, and jazz artists perform at Tanglewood each year.

In the past, some of the big names who have performed at the festival include Janis Joplin, Whitney Houston, Bob Dylan, Beach Boys, and John Denver.

The Koussevitzky Shed and the Ozawa Concert Hall are two big concert spaces inside the Tanglewood estate.

The expansive outdoor lawns are backed by views of the Monument Mountain and Stockbridge Bowl, a lake in nearby Stockbridge.

Picnics are a key component of the Tanglewood experience. The festival also provides plenty of dining options across its campus. 

Take a look at the Tanglewood schedule and book your concert tickets for the summer. 

The Tanglewood lawns are also a great walking spot on a sunny day. Visitors are welcome to walk-in on non-concert days, free of charge. 

If you enjoy audio tours, listen to this narrated tour of the grounds during your visit. 

You could also choose an audio selection of BSO’s past performances to accompany your walks!

Views from the top of Lenox Mountain
Outstanding views from the top one of Lenox MA. Photo: Liza

See breathtaking vistas from the top of Lenox Mountain 

Wondering what to do in Lenox MA on a bright sunny day? Consider hiking the moderately challenging trail to the top of Lenox Mountain.

Here’s what’s in store if you do: Spectacular views of Mount Greylock to the north, the Taconic Range to the west, and the Catskills in the southwest!

There are two ways to ascend Lenox Mountain. 

You could either park your car at the Mass Audobon Pleasant Valley Sanctuary and proceed to walk up the 850-foot Trail of Ledges. 

This route can get pretty steep, and slippery, and should be only taken on the way up.  

To return, take the pleasant Overbrook loop, which follows the course of a stream. 

Or, park your vehicle at end of Osceola Rd and hike the unmaintained extension of the road. Turn left ascending to the Richmond Fire Tower at the top of Lenox Mountain.

The entire hike could take upwards of 3 hours. 

Lenox Mountain is also ideal for skiing, snowshoeing, and mountain biking. 

Sunlight and fall foliage against tall trees at Pleasant Valley Wildlife Sanctuary, Lenox MA
A hike inside Pleasant Valley Wildlife Sanctuary is amongst one of the top things to do near Lenox MA. Photo: Good Bites & Glass Pints

Indulge in hikes & birdwatching at Pleasant Valley Wildlife Sanctuary

Since 1929, the Pleasant Valley Wildlife Sanctuary has been providing a scenic family-friendly environment for nature exploration.

The sanctuary offers 7 miles of walking trails. Depending on your level of interest, you could choose to pursue one or all three trails!

If you’re interested in birding, opt for the 1.5-mile long Beaver Lodge Trails Loop. This easy trail can be completed in about an hour.

If you enjoy challenges, opt for the Ledges/Overbrook Loop with a vertical 850-foot ascent. The scenic vistas from the top of Lenox Mountain make this trail worth the while. 

On your return journey, take the Overbrook trail which follows a stream. 

The flat and easy All Persons Trail/Pike’s Pond Trail Loop is the lightest trail in Pleasant Valley. In less than a mile, you would reach a deck overlooking a beaver pond. 

While this trail is kid-friendly, it is currently closed due to a devastating storm that hit the Sanctuary in 2021. 

Staying in Western Massachusetts?
Read about these 20+ amazing things to do in the Berkshires region.

Tall trees and a hiking trail inside Kennedy Park Lenox
Whether you wish to hike, mountain bike, ski or go on a horseback ride – there’s something for you at Kennedy Park, Lenox MA. Photo: Dawn & John Whalley

Enjoy a day hike inside Kennedy Park

Located five minutes outside of the Lenox town center, Kennedy Park is a local favorite for all kinds of activities. 

The trails inside the park are not only hiker friendly, but they are also ideal for mountain biking, skiing and horseback riding. 

There are several trails inside Kennedy Park, and here is a handy map of all the trails along with the difficulty level included. 

You could start at the Arcadian Shop and grab a physical map too. 

The Kennedy Park short loop is a 7-mile pleasant trail. 

There’s also a 13-mile Kennedy Park medium loop and a 3-mile Burbank Trail from Olivia’s Overlook. 

Kennedy Park also has picnic benches, and the trails are dotted with beautiful foliage in the fall season. 

Views of mountains and Stockbridge Bowl from Olivia's Overlook in Lenox MA
Looking for one of the best things to do in Berkshires? Head to Olivia’s Overlook for a stunning viewpoint. Photo: Tim Grafft/MOTT

Soak in breathtaking views of Stockbridge Bowl from Olivia’s Overlook

If you’d like to see one of the most beautiful sights in all of Berkshires, head to Olivia’s Overlook, located in the 734-acre Yokun Ridge South reserve.

Though technically located in Stockbridge, Olivia’s Overlook is just three miles away from Lenox town center.  

You would be treated to spectacular views over Stockbridge Bowl, even if you visit the parking area. 

Olivia’s Overlook is located by the parking area, and is also the trailhead for the Charcoal Trail and the Brothers Trail. 

The reserve, including most of present day Berkshires, used to belong to the native Mohican people. 

In the Gilded Age, the area became a part of an estate owned by a financier whose daughter was named Olivia Hatch. 

Olivia’s Overlook and the Brothers Trail are named after Olivia and her brothers, who decided to donate the land for this protected area. 

The 1.6-mile Charcoal Trail is a flat-rounded loop that provides hikers with views of Monument Mountain, Richmond, and West Stockbridge.

The one-way, moderately challenging 0.9 mile Brother’s Trail is connected to the Charcoal Trail. 

Brother’s Trail connects the Charcoal Trail to the Old Baldhead road, which leads to Monks Pond. 

Directly across the road from Olivia’s Overlook is the starting point for the 3.2-mile long Old Burbank Trail. 

Because of its beauty, Olivia’s Overlook is a popular spot in the Berkshires, and parking during the busy summer season can be tricky.

If you’re visiting in the summer or fall, plan to visit the overlook early in the day!

Greenery and benches at Lilac Park in Lenox MA
Looking for a quiet green space to relax in Lenox MA? Head to Lilac Park! Photo: Good Bites & Glass Pints

Slow down and enjoy the charm of New England at Lilac Park

Located in the historic district of Lenox, Lilac Park is a 1.5-acre green space and a great lounging spot in the center of the town.

The park consists of picnic benches and a gazebo for bands to perform.

Numerous shrubs, plants and trees have been added to the park, courtesy of the Lenox Gardening Club.

The park is an ideal place to rest in the middle of the day. You could even carry a blanket and a picnic lunch and enjoy a meal outdoors during warm days. 

In the summers, Lilac Park plays host to a series of free concerts during the weekends. 

Love visiting New England towns? Check out these 11 things to do in Williamstown MA, another beautiful town in the Berkshires

The exquisite dining hall at Ventfort Hall, Lenox MA
Known for its woodworking and Jacobean style architecture, Ventfort Hall is a Gilded Age museum in Lenox MA. Photo By: David Ryan

Love architecture? Visit the Ventfort Hall & Gilded Age Museum

Described as “one of the most beautiful places in Lenox”, Ventfort Hall is a 19th Century Gilded Age mansion belonging to Sarah Morgan, the sister of the noted investment banker, J.P. Morgan.

Designed in Jacobean architectural style, the house consisted of 28 rooms and a total of 28,000 square feet of living space!

Ventfort Hall is especially known for its woodworking. Designed by Rotch & Tilden, it was among the seventy-five countryside “Berkshire Cottages” built in the Lenox / Stockbridge area. 

Today, portions of Ventfort Hall are under careful restoration and its first floor is completely open to the public. 

Through lectures, performances, events, and guided tours, the Museum is preserving stories of the fascinating Gilded Age alive. 

Barring Wednesdays, the museum is open on all days for self-guided tours, the best way to make the most of your visit is by joining a guided tour.

Tours cost $18/per adult. 

Audio tours are also accessible via smartphones in every room. 

Interested in seeing a few more historic homes and museums? Take a look at this round up of incredible museums in Berkshires!

Landscape view of The Mount and its formal gardens
Looking for things to do in Lenox MA in summer? A visit to The Mount might be your answer! Photo: Depositphoto|iriana88w

Meander through the lovely gardens at The Mount

Located down the road from Tanglewood in Lenox and the Norman Rockwell Museum in Stockbridge, the Mount is writer Edith Wharton’s home.

Wharton, the author of The Age of Innocence, Ethan Frome, and The House of Mirth, designed the home herself.

The house, inspired by French, Italian and English traditions, is a visual treat to the eyes. 

The estate consists of the main house, formal gardens, and stables. Today, the property also has a terrace cafe and a bookstore. 

While the gardens are free and open for visitors daily, tours of the main house begin in May. 

The Mount also hosts several exhibits and a variety of events each year. 

Visitors can also participate in “ghost tours” that are immensely popular. 

Entry to The Mount costs $20 for adults. Children under 18 go free.

See a live theatre act at Shakespeare & Company

Since its establishment in 1978, the Shakespeare & Company has been producing exceptional theatre performances, engaging an audience of over 40,000 each year.

Located on Kemble Street in Lenox, it is one of the largest Shakespeare festivals in the country.

Their dedication to telling compelling stories coupled with their unique approach to the works of William Shakespeare is not just inspiring but also refreshing!

Recently, the Company has built a brand new Spruce Theatre that elevates the outdoor live theatre viewing experience. 

Here is their seasonal line-up. Book tickets now!

Check out whimsical art pieces at Tom Fiorini Sculpture Yard

A permanent fixture in Lenox MA for the past thirty years, Tom Fiorini’s sculpture garden is for art and humor enthusiasts alike. 

Situated on Church St., Tom’s scuplture garden reflects his creativity and whimsy nature. 

His scupltures and art pieces are displayed in the open and are built of metal, wood, everyday items and even scrap. 

Tom’s art pieces have been purchased by travelers from Europe, Australia and residents of all fifty US states. 

If you enjoy admiring unique works of art, Tom Fiorini’s sculpture yard should be on your visit list!

Hotels in Lenox Massachusetts

Being home to Tanglewood makes Lenox MA a busy place in the summers. Needless to say, there are several stays in the region that cater to every kind of budget and family size. 

Whether you’re looking for luxury, comfort or convenience, these hotels in Lenox MA are located close to all major attractions and have been hosts to several satisfied guests. 

Luxury: Hampton Terrace Inn

This well maintained, historic property in the heart of the Berkshires began welcoming guests the same year as the Tanglewood was established! Hampton Terrace Inn is adorned with antique furniture, plush bedding and provides all kinds of modern day comforts that you could think of! They have a tennis court, an outdoor pool, and guests have particularly raved about their gourmet breakfast. 


Mid-Range: Apple Tree Inn

Originally built as a mansion on a hill in 1885, the Apple Tree Inn is known to have a warm atmosphere, friendly staff and comfortable rooms. Located very close to Tanglewood, and next to the Kripalu Center, the inn has a pool, a fabulous bar and restaurant, and stunning views. 


Budget: Howard Johnson by Wyndham Lenox

Located three miles from the town center, Howard Johnson by Wyndham Lenox offers clean, spacious rooms, an outdoor pool and a grab and go breakfast and picnic area. Guests have particularly liked the comfortable beds in the room and the central location of the hotel. 

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