Skip to content

Things To Do in Lenox MA For A Great Weekend Away!

Are you looking for fun things to do this weekend? If you are this is one of the most rewarding weekend destinations I have found. It’s a lovely town located on the northeast called Lenox Massachusetts.

Tucked away in the southwest section of the state, near the New York border and what you’ll find is that there are so many fun things to do in Lenox MA!

It combines a country setting with a rich cultural heritage full of outstanding historic houses to visit, delightful art and music festivals during the summer, and museums to feed the mind.

You can stay or dine in historic mansions, enjoy a wealth of outdoor activities, and shop in charming village main street surroundings. I have enjoyed visiting Lenox both in summer and winter. But in every season you’ll find it a perfect weekend trip or a base for a longer stay in the Berkshires region.

The Mount - Edith Wharton's Home - Lenox, Massachusetts

10 Fun Things to Do in Lenox Ma

I wondered how this small town had become so famous, and the setting for such luxury and culture. Back in the late 1800s, the wealthy from New York and Boston found the area’s natural attractions irresistible.  They joined like-minded friends in building what were then called “cottages”, large mansions to enjoy the summers away from the city.

This was during the so-called Gilded Age when there was extraordinary wealth earned from new industries such as the railroad and coal mining.

Here are ten great things to do when visiting Lenox:

1) Stay at a Gilded Age Mansion


View this post on Instagram


A post shared by John Waskiewicz (@john_waskiewicz)

When considering lodgings for your time in Lenox, you have the tantalizing prospect of choosing one of the Gilded Age mansions that have been turned into luxury hotels. I had the pleasure of staying at Cranwell Resort, which has now become the Wyndhurst Manor and Club, a historic mansion perched on a hilltop in Lenox.

Other spectacular former Gilded Age houses that offer accommodations and fine dining include:

* Blantyre, a Tudor-style mansion built in 1902,

* Canyon Ranch, which is a nutrition and wellness resort situated in the historic Bellefontaine mansion, and

* Wheatleigh, an Italianate-style country home built in the 1890s.

former gilded age mansion, now luxurious hotel in Lenox Ma

Recommended Reading:

2) Visit a Historic House Museum

I have always enjoyed the feeling of stepping back in time when touring a historic home. I like learning more about its occupants and how they lived. Among the best things to do in Lenox MA is visiting some of the Gilded Age mansions that are open as museums.

Being an avid reader, my top choice would be The Mount, the beautiful mansion and gardens built in 1902 by Pulitzer Prize-winning novelist Edith Wharton, who penned such books as The Age of Innocence and Ethan Frome.


View this post on Instagram


A post shared by Natalie Aldridge (@natalieealdridge)

Other historic houses to see are:

* Ventfort Hall Mansion, a red brick Jacobean-style mansion built-in 1893 for the sister of J.P.Morgan and housing The Museum of the Gilded Age.

* Naumkeag estate in Stockbridge was designed by famed New York architect Stanford White, and its gardens are a star area attraction. Don’t miss the Blue Steps, a series of pools bordered by stairs and birch trees!

* Chesterwood was the Stockbridge home of famed sculptor Daniel Chester French, who created the Minute Man statue and the Abraham Lincoln Memorial in Washington D.C.

* Arrowhead is the former home of author Herman Melville, who wrote his famous novel Moby Dick here. The house is located in nearby Pittsfield.


View this post on Instagram


A post shared by Desiree (@gothamsgildedage)

Recommended Reading:

3) Admire Art in Great Local Museums

There is such an amazing concentration of the greatest collections in Lenox and the surrounding Berkshire towns.

Nearby Stockbridge was the home of artist Norman Rockwell for the last 25 years of his life. The biggest collection of his work is at The Norman Rockwell Museum in Lenox, where you can learn about Rockwell’s art capturing the essence of Americana.

One of the most notable parts of the collection for me is his series of covers for the Saturday Evening Post. Rockwell used local residents as his models, and the portraits of small-town residents and life are priceless.

Other extraordinary art collections in the Berkshires area include:

Mass MOCA (Museum of Contemporary Art) in North Adams offers a fascinating collection of modern art in a sprawling complex of galleries in a former factory.

* Clark Art Institute in Williamstown has a fantastic collection of paintings, sculptures, and decorative arts worth a special visit for art lovers.

* Williams College Museum of Art emphasizes modern and contemporary art on the college’s campus in Williamstown.

* Freylinghuysen Morris House and Studio has a collection of American and European Cubist art on a 46-acre estate in the heart of Lenox. George Morris and Suzy Freylinghuysen were abstract American artists.  You can also see their own paintings and sculpture here.

4) Learn about Local History

When visiting Lenox MA, take the opportunity to learn more about its history by visiting some of its historic museums. Two of the most interesting for local history are:

* The Berkshire Museum has wide-ranging collections of art and history.

* The Berkshire Scenic Railway offers train buffs a close-up look at the historic train station and railroad cars plus even a short ride on the museum grounds!

An old steam locomotive steam train

Recommended Reading:

5) Attend a Festival

Summer is prime time for festivals, and these are some of the best I’d like to see:

* Tanglewood is the summer home of the Boston Symphony orchestra and has hosted the famous Tanglewood Music Festival during the summer since the 1930s. Have a picnic on the lawn while listening to great artists perform! A wide variety of musical acts take the stage at Tanglewood, so you’re sure to find something to suit your tastes.  Just book early as the summer season tickets book fast!

* Jacob’s Pillow is the dance equivalent to Tanglewood and brings dance troupes from all over the world held in nearby Becket MA. Here you will see an eclectic variety of international dancers performing in a beautiful Berkshires setting.

* Shakespeare and Company has been offering classic Shakespearian plays plus new offerings in Lenox since 1978.

* The Williamstown Theater Festival, another only-in-summer treat!

Here are some other excellent regional theater companies when considering things to do near Lenox MA:

* Barrington Stage Company in Pittsfield.

* Berkshire Theater Group offers theatrical performances with three stages in Stockbridge and Pittsfield.

* Mahaiwe Performing Arts Center in Great Barrington.

Other Things to do in Lenox MA

6) Enjoy the Outdoor Beauty

Among Lenox MA attractions, getting outdoors to enjoy the local beauty for walks or hikes is highly recommended! Here are some of the natural attractions to enjoy:

* The Pleasant Valley Wildlife Sanctuary offers over 1,000 acres of beautiful forest and meadow areas with seven miles of trails to explore. You may spot beavers building their dams along the river!

* Kennedy Park offers 15 miles of trails and is a great place for a picnic or to take in the Fall foliage! And the park is adjacent to the center of town, so it’s easy to add a hike to your activities.

* Berkshire Botanical Garden offers 24 acres of beautiful blooms in Stockbridge, with spring and summer the peak viewing seasons.

* Popular hiking destinations in the Berkshires would include Monument Mountain in Great Barrington, Mt. Greylock (the highest peak in Massachusetts) in Lanesborough between Adams and Pittsfield, and Bish Bash Falls in Mt. Washington near the New York state line.

7) Visit a Historic Site

Shaker village Hancock, Lenox Massachusetts

When considering things to do near Lenox, a visit to the historic Hancock Shaker Museum in Pittsfield would be a great choice. This fascinating collection of 20 historic buildings on 750 acres is a living history museum that describes the life religious community known as the Shakers.

This group came from England originally and was a communal society known for its crafts, music, and art, which you can see on display here. Don’t miss the famous round stone barn!

Recommended Reading:

8) Go Skiing or enjoy other Wintertime Outdoor Activities

There are several good skiing options for those who want to mix outdoor recreation with the charm of the village covered in snow and filled with decorations over the holiday season.


View this post on Instagram


A post shared by @goongear

There are several fun downhill ski destinations within a short drive from Lenox, including Jiminy Peak, Catamount, Bousquet Mountain, and Ski Butternut. Other wintertime snow sport options include sledding and tubing, ice skating, or even taking horseback rides on snowy trails!

9) Go Shopping and Dining

Lenox is a charming town with a downtown full of shops and restaurants. So part of your top things to do in Lenox Massachusetts will likely include taking time out to do some shopping. And of course, you’ll want to experience some of the best local dinings!

Browse the streets of the village for local crafts, antiques, and art in the galleries.  There’s even a local bookstore with its own wine bar. A whimsical stop would be to view the sculpture of longtime local resident Tom Fiorini.  His eclectic sculptural works are on display in his yard on Church St. across from the Scoop Ice Cream Shop.

The tempting Lenox restaurant scene will satisfy the palate for a broad range of cuisines. You might want to experience a more formal meal at The Gateways Inn and Restaurant, or at the Portico at the Wheatleigh estate, which has only eight tables.

I enjoy farm-to-table restaurants and one of the best in Lenox is Nudel at 37 Church Street. With a menu that changes nightly to focus on what’s in season, Nudel offers up creative cuisine.

What else might make your list for weekend dining? Wine and tapas are on order at Brava, and gastropub fare at Firefly.  You’ll find delicious Italian favorites at Frankie’s Ristorante Italiano and hearty breakfasts at Haven.

Or choose from Mediterranean-inspired selections at Alta, French favorites at Bistro Zinc, and chocolate decadences at Chocolate Springs Café.

10) Exercise your Mind and Body

Things to do in Lenox Ma, couple exercising in the countryside

Sometimes just having some downtime for relaxation is just what the doctor ordered while on vacation. With that in mind, here are some places to add to your Lenox Massachusetts things to-do list when exercise and peaceful contemplation top your wish list!

Canyon Ranch Resort is located in the historic Bellefontaine Mansion built-in 1897 as a summer home for a wealthy financier.  It is now home to the Canyon Ranch Health & Wellness Resort & Spa, which has a full program and wellness activities to take advantage of amidst bucolic surroundings.

Another place in Stockbridge to relax and enjoy the beautiful surroundings is by indulging in some yoga at the Kripalu Center for Yoga and Health.

As I learned, the list of things to do in Lenox MA is quite extensive.   You’ll probably be planning your next weekend getaway there on your way home! No matter the season, you’ll find enticing historic attractions.

Consider fall for outdoor scenery for hikes and leaf-peeping.  Winter brings snow-covered landscapes and skiing.  Summer is festival time, with amazing music and dance performances at Tanglewood and Jacob’s Pillow.

Recommended Reading:

If you are interested n the history of Lenox you will find these articles fascinating as you learn more about the Founding of Lenox and the Gilded Age when the fabulous estates were built and the personalities behind them.

This will help you dig into why Lenox has become a choice destination for wealthy northeastern families.  What was it about the Gilded Age that enabled the rich and powerful to build such lavish testaments to their riches?

And check out this video for a visual overview of some of the top sights in Lenox.


Additional Artistic, Historic, and Festival Centered Travel Ideas

If you’re a fan of the arts, festivals, and historic homes here are some additional vacation planning suggestions you may want to consider next.

California’s Maloof Foundation for Arts and Crafts in Alta Loma is a great artistic experience.

Heading north to Toronto, historic house enthusiasts will find the Casa Loma intriguing.

Festival fans may find the Minnesota version of Oktoberfest delightful with its food and music.  Or check out the major festivals in Thailand for the best times to visit that fascinating Asian nation.

And what art lover doesn’t dream of a trip to Italy?  To help bring those dreams to reality, here are some must-sees there to consider when planning a trip to this art-rich country.

Final Thoughts

So there you have it, some fun things to do in Lenox Ma, if you are looking for a great weekend away!

Now, it’s your turn, comment below and let us know have you been to Lenox Ma? What did you enjoy most about your trip? If not what are you looking forward to the most when you finally do visit!

Thank you for reading!