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Nestled in the heart of the Berkshires in Western Massachusetts, Lenox offers the perfect blend of natural beauty, cultural attractions, and a vibrant arts scene. Arguably one of the most famous towns in Berkshire County, its claim to fame is the Boston Symphony Orchestra’s Tanglewood concert series, and Canyon Ranch, one of the most well-known luxury spas in the US.
“Ah, so Lenox is a RICH rich town,” I thought as I prepared to visit. And honestly…that’s not too far from the truth.
Lenox is situated at the foothills of the Berkshire Mountains, surrounded by lush forests, rolling hills, and sparkling lakes. This scenic location makes Lenox an ideal destination for people who love the outdoors as much as they love the arts.
The town center is a pleasant place to explore on foot, with a number of shops, restaurants, and art galleries. The town also has a number of historic homes, including the Mount, which was the home of Edith Wharton.
At first glance, Lenox appears to cater to the rich. But don’t be fooled by the elite exterior; there is a lot to experience and enjoy. Whether it’s a relaxing weekend in the Berkshires or a quick day trip from elsewhere, Lenox is a destination that I think is very much worth visiting.
(Planning a trip to the Berkshires? Be sure to check out the Best Things to Do in the Berkshires and my guide to the Towns of the Berkshires.)
This post was published in January 2024 and was co-written by Adventurous Kate and Susan Stephens.
Table of Contents
The Best Things to do in Lenox, MA
Experience the Tanglewood Music Festival
The number one thing to do in Lenox, without a question, is to experience the Tanglewood Music Festival. Tanglewood is the summer home of the Boston Symphony Orchestra, and it is one of the most popular attractions in Lenox. The Tanglewood Music Festival takes place every summer, and it features a variety of classical, jazz, and popular music concerts.
The festival is spread across multiple venues on the Tanglewood grounds. The main venue is the Koussevitzky Music Shed, which hosts the Boston Symphony Orchestra’s summer concerts. There are also a number of smaller venues that host chamber music, jazz, and other types of performances.
I have friends who attend John Williams night at Tanglewood every year, featuring his most memorable film scores, from Star Wars to Jurassic Park to Home Alone. I need to attend that someday!
Tanglewood is a beautiful place to visit in the summer months, even if you don’t attend a concert. There are guided tours of the estate’s gardens and grounds, as well as lectures, workshops, and other educational programs.
You can purchase tickets to individual concerts, or you can buy a lawn pass book, which allows you to picnic on the lawn while you listen to the music. Student, military, and group rates are also available. You can see all details on visiting Tanglewood here.
Have a Spa Day at Canyon Ranch
Canyon Ranch in Lenox has long been known as one of the best spas in the United States. And with that come sky-high prices. Come stay for a weekend and leave feeling like a new human…just know that it will cost you a pretty penny.
However, a lot of people don’t know that Canyon Ranch also offers a far more affordable day spa option. For $350, you can enjoy a 50-minute facial or massage; access to the pools, saunas, and whirlpools; access to the beautiful grounds and restaurant; and fitness classes, among other things.
A spa day is the perfect interlude for your Berkshires adventure! My best girlfriends and I keep talking about booking this one weekend…
Visit Ventfort Hall
Ventfort Hall is a historic mansion that was built in 1893 by George and Sarah Morgan (sister of J.P. Morgan) as a summer home. A testament to the Gilded Age, the mansion is now a museum that is open to the public. Visitors can tour the mansion’s 28 rooms which are filled with opulent furnishings and art. The mansion also has a beautiful garden that is perfect for a stroll.
I loved touring Ventfort Hall, and I have to give a shout-out to the guides, who are so knowledgeable and passionate about this building, eager to share tidbits about the architectural quirks. Also, The Cider House Rules was filmed here!
Open year-round, daily guided tours are available. Admission to Ventfort Hall is $18 for adults, $17 for seniors and healthcare workers, $10 for students ages 18-23 with ID, $7 for ages 5-17, and free for children under 5.
Tour Edith Wharton’s The Mount
The Mount is the former home of the Pulitzer Prize-winning author Edith Wharton, and visiting here is easily one of the best things to do in Lenox MA. Wharton spent much of her prolific writing years here, and today it is among the most stunning historic homes in the region.
Her wonderful sense of style is still prevalent in the furnishings (the dining rooms are especially sumptuous and colorful). The Mount also has a beautiful garden that was designed by Wharton herself. My friends who grew up in the Berkshires would often come here to walk year-round.
One big reason Edith continues to be relevant today, more than 80 years after her death, is largely due to the authenticity of her writing. She was a keen observer of society and perhaps more importantly, what it means to be human.
The museum offers guided tours of the house and grounds, and it also hosts a variety of events, including lectures, concerts, and exhibitions. Admission to The Mount is $20 for adults, $18 for seniors, $13 for students with ID, $10 for the military, and free for children under 18. The grounds are free to visit.
Appreciate the Arts
Lenox is a small town full of artistic attractions that are right under your nose. Three of the most notable include the Tom Fiorini Sculpture Yard, Glendale Brook Studio, and Sohn Fine Arts.
The Tom Fiorini Sculpture Yard is an outdoor museum dedicated to his work. As a sculptor known for abstract metal creations, visitors can wander through the yard and admire the sculptures, which range from small tabletop pieces to monumental works that soar overhead. The yard is open to the public and is a great place to spend an hour or two exploring and taking in the beauty of his work.
Glendale Brook Studio features the work of Alex Kamaroff. Visitors are invited to tour the studio and observe his creative process. Kamaroff’s painting technique is described as “a messy kind of magic,” in which he uses only artist’s tape, acrylic paint, and a hair dryer. The result is a modern twist on the whimsical. The gallery is open seasonally, usually from March through October.
Sohn Fine Arts is a contemporary art gallery located in the heart of Lenox. The gallery represents a diverse group of emerging and established artists, showcasing a variety of media but focusing on contemporary photography. The gallery also hosts exhibitions and events throughout the year, providing a platform for artists to share their work with the public. Visitors can browse the gallery’s collection and find unique pieces to add to their own collection.
Gilded Age Museum
The Gilded Age Museum, housed within the opulent Ventfort Hall Mansion, transports visitors back to the grandeur and extravagance of the Gilded Age. Within its walls is a unique experience, allowing visitors to step into the shoes of the wealthy and immerse themselves in the extravagance of the era.
Admission here is included in visiting Ventfort Hall.
Berkshire Scenic Railway Museum
Contrasting with the opulence of the Gilded Age, the Berkshire Scenic Railway Museum showcases the region’s industrial heritage and the enduring power of transportation.
The museum’s highlight is the restored New Haven Depot which is on the National Register of Historic Places. Guided tours are available, and visitors can also board and experience the thrill of a train ride through the Hoosac Valley. (Wishing there were more trains in New England? Well…there you go!)
Admission to the Railway Museum is $15 for adults, $12 for seniors, and $5 for children ages 5-16. It is open seasonally from Memorial Day through Labor Day on Saturdays.
Stay in a Gilded Age Mansion
Lenox was a popular summer destination for wealthy Americans in the late 19th and early 20th centuries, and many of the town’s Gilded Age mansions are now open to the public as award-winning lodgings. Some of the most popular Gilded Age mansions in Lenox include Blantyre (reopening in late 2024), Wyndhurst Manor and Golf Club, Wheatleigh, and of course, Canyon Ranch.
These magnificent homes were built by wealthy industrialists and financiers back in the day and they offer a glimpse into the opulent lifestyle of that era. If you’re looking for a truly unique experience, consider staying in one of these opulent properties.
They offer a variety of amenities including luxurious guest rooms, fine dining, spa services, and stunning views of the Berkshires.
Catch a Performance at Shakespeare & Company
Shakespeare & Company is a renowned theater company based in Lenox. Immerse yourself in the summer performance season that brings to life the timeless works of Shakespeare, alongside a captivating array of classic and contemporary plays.
This professional theater company is well-known in the Berkshires and presents one of the most extensive actor training programs in the country. It is also home to an award-winning, nationally recognized theatre-in-education program.
The company offers a variety of educational programs, including workshops, classes, and summer camps. So whether you’re looking for a great night out or a fun educational experience, this is the place to go!
Visit the Lenox Library
Housed in a stately Greek Revival building, the Lenox Library is a relaxing place to learn about the town’s history and culture. Within its walls, visitors will find an impressive collection of historical documents, photographs, and artifacts that tell the story of Lenox from its early days as a farming community to its transformation into a popular tourist destination.
And just like any good library, you’ll find a healthy collection of over 100,000 books. The Lenox Library holds a special place in the intellectual, historical, and cultural landscape of the city. The library also offers a variety of programs and events, as well as lectures, concerts, and exhibitions.
Enjoy the Outdoors
Just minutes from the center of Lenox lies Kennedy Park, a serene oasis where the rustling of the trees adds their own soundtrack to woodland walks. Hikers will revel in 15 miles of groomed trails, including a short stroll to a scenic waterfall and a more challenging climb through hemlock and pine forests. Trail access is via Main Street next to Church on the Hill, as well as via Route 7.
Another escape is to a 1000-acre haven for wildlife and outdoor recreation called Pleasant Valley Wildlife Sanctuary. Take a peaceful walk through meadows and dense forests on miles of extensive trails while keeping an eye out for deer, foxes, and more. Avid birdwatchers should visit the sanctuary’s many wetlands, where they can catch sight of herons, egrets, and the occasional osprey. Admission to Pleasant Valley Wildlife Sanctuary is $5 for adults, $3 for seniors, and $3 for children age 2-12.
For a bit of fresh air in the heart of Lenox’s Historic District, Lilac Park is a fragrant sanctuary. It is home to over 1,000 lilac bushes that burst into vibrant bloom each spring. Take a stroll through the park’s peaceful gardens, stopping to admire the colorful blossoms and inhale their sweet aroma. When it’s time to stretch your legs, explore the network of walking trails that wind through the park’s wooded areas.
Parsons Marsh Reserve is located just a few miles west of Lenox. This reserve is a wonderful place to go for a hike, mountain biking, or just to appreciate the serenity and wildlife. There are many vernal pools that provide a perfect breeding ground for amphibians. The reserve’s extensive trail system takes hikers through marsh wetlands, where they can observe resident wildlife such as muskrats, painted turtles, and more.
If you’re looking for a more challenging hike, you can try a portion of the Appalachian Trail in Massachusetts, which passes just east of Lenox.
Go Cross-Country Skiing
The Berkshires are a year-round destination, and if you visit in the winter, Lenox is a great place to do some cross-country skiing! Here are some of the best places to go cross-country skiing in and around Lenox:
Located just a short drive from downtown Lenox, Kennedy Park offers 15 miles of groomed tree-lined trails for cross-country skiing. The trails wind through meadows and forests, offering beautiful views of the surrounding mountains. The ski terrain is mostly flat and smooth, but for those who want a bit more of a workout, challenging trails are nearby.
Canterbury is a local farm that offers several miles of groomed trails with various terrain; not for the beginning skier! Also, October Mountain State Forest is the largest state forest in Massachusetts, and here you’ll find over 16 miles of trails for cross-country skiing which are groomed regularly.
Hike Lenox Mountain
Lenox Mountain is a popular hiking destination that offers stunning views of the Berkshires. The mountain is located just a short drive from Lenox. There are a number of different trails that you can hike on Lenox Mountain, ranging from easy to difficult. Note that some are not clearly marked or maintained, as it lies on the ancestral land of the Mohican people.
For a nice hiking challenge, Lenox Mountain is a great place to go. Take the Trail of the Ledges and/or Overbrook Trail through northern a hemlock forest to Lenox’s highest peak. It is about three miles roundtrip and it offers stunning views of the surrounding area.
In the winter, the trails can be icy, and I recommend that only experienced winter hikers tackle this route.
Sip Wine in a Bookstore
Escape to The Bookstore and Get Lit Wine Bar, where literature and libations collide. Located in the heart of Lenox’s adorable downtown, this unique bookstore offers an experience that’s as rich and full-bodied as your favorite Cabernet.
Browse through a carefully curated selection of books, ranging from beloved classics to contemporary bestsellers, and discover hidden treasures that await on every shelf. The knowledgeable staff is passionate about both books and wine and is always on hand to assist you in finding the perfect read. Pair it with an exquisite glass of vino from their extensive collection and you are set for the afternoon.
What sets The Bookstore and Get Lit Wine Bar apart is its commitment to fostering a sense of community. Regular author events, book clubs, and themed gatherings provide opportunities for connection and discussion.
Try Forest Bathing
This is a unique experience! Where the trees stand tall and the air is thick with the scent of pine, lies something special: a two-hour, guided forest bathing session that will transport you to a realm of mindfulness and a deep connection with nature.
Slow down, breathe deeply, and let the forest embrace you. Immerse yourself in the symphony of sounds, the tapestry of textures, and the intoxicating aromas that surround you.
With each step, you’ll be guided on a journey of self-discovery. Engage in short, contemplative walks, and pause to explore the wonders of nature through guided invitations. Discover the hidden secrets of the forest and forge a profound bond with the ancient trees. No equipment or special skills are required, just an open heart and a willingness to surrender to the beauty of the forest.
Attend a Festival in Lenox
Yes, Tanglewood is the big summer festival in Lenox. We all know that one! But what about the other festivals Lenox has to offer?
If you’re visiting in early June, check out the Rhubarb Festival. This festival celebrates the vegetable in every form — oh, and there are plenty of strawberry rhubarb pies on hand. And cakes. And cookies. I’m sorry, what were we saying?
And if you happen to visit in the fall, the Lenox Apple Squeeze is a good one, with a beer tent for adults, activities for kids, and musical performances; and The Fall Festival of Shakespeare brings some of the best Shakespearean talents and enthusiasts to the Berkshires for once-in-a-lifetime performances.
Visit other towns in the Berkshires
There are lots of towns in the Berkshires worth visiting while you base in Lenox. Here are a few of my favorites:
Stockbridge
Situated just a stone’s throw south of Lenox, Stockbridge offers a quaint charm that’s perfect for history enthusiasts. Stroll through the Berkshire Botanical Garden for a moment of tranquility, then visit Chesterwood, the former home of sculptor Daniel Chester French, creator of the Lincoln Memorial.
The Norman Rockwell Museum is here as well and well worth a visit. Don’t miss the bustling Main Street lined with eclectic cafes, shops, and the Red Lion Inn.
See more in my guide to Stockbridge here.
Great Barrington
Just 13 miles south of Lenox, Great Barrington beckons with its eclectic mix of culture. Take a walk along the Housatonic River Walk, then head to the walkable downtown to peruse the many cool shops.
One nice aspect of Great Barrington is its urban feel situated near Monument Mountain; just right for an energetic hike and views over the landscape.
North Adams
A former mill town turned artistic enclave, North Adams is nestled 30 miles north of Lenox. Explore the world-renowned Massachusetts Museum of Contemporary Art for a one-of-a-kind art experience, or relax in Natural Bridge State Park, home to the only natural white marble arch in North America!
North Adams embodies a great story of a town that has revitalized itself with its art and culture. I can’t wait to see where it will be 10 years from now.
Williamstown
Next door to North Adams, Williamstown is a college town where history, culture, and art collide. Admire the impressive architecture of the Clark Institute, with one of the best collections of Impressionist art on the planet (seriously, it’s up there with Paris and New York).
For a theatrical treat, the Williamstown Theatre Festival showcases captivating performances in the summer. Its tiny downtown offers a good share of shops and restaurants, many catering to the college crowd.
How Much Time to Spend in Lenox
While you can technically squeeze in the highlights of Lenox in a single day, I think two days would give you a lot more time to see the town’s highlights. Maybe even a third day if you’re spending a day at Canyon Ranch!
If you’re planning on pampering yourself with spa treatments or attending several performances, definitely allocate more time to indulge in the town’s relaxing atmosphere and partake in its many cultural offerings.
How to Get to Lenox
To truly experience the Berkshires, I strongly suggest renting a car. While there are cabs and extremely limited public transportation options, having your own set of wheels will give you the freedom to explore the region at your own pace.
There is no Uber service in Lenox. The closest airport is in Albany, about an hour’s drive away, but if you’re flying in from Boston (the nearest major international airport), you can hop on a bus from Boston year-round.
Amtrak has a station in Pittsfield, Mass., not too far from Lenox. And Amtrak’s seasonal Berkshire Flyer runs from New York to Pittsfield. You can rent a car in Pittsfield if you’d like, but I recommend doing so in advance, as it’s a small rental without a huge selection.
Where to Stay in Lenox
For maximum walkability, I recommend opting for a hotel in downtown Lenox. Unless you have a special Gilded Age mansion in mind, which is its own kind of stay!
Top-Rated Luxury Hotel in Lenox: The Cornell Inn — This stunning lilac Victorian bed and breakfast combines historic charm with modern amenities. The recently renovated rooms are a feast for the eyes, featuring bold statement pieces and luxurious touches.
Top-Rated Mid-Range Hotel in Lenox: Seven Hills Inn — This inn has a much more resort-like feel, with cozy living rooms, an inviting fire pit, an outdoor chess set, and a refreshing pool. It’s an incredible value for money, especially during the off-season.
Top-Rated Budget Hotel in Lenox: Quality Inn (Lee) — There aren’t any budget hotels in Lenox, so I recommend you take a look in the town of Lee, about a 15-minute drive from Lenox. While it may not be the most aesthetically pleasing, this small inn offers clean, comfortable rooms at a budget-friendly price.
Best Time to Visit Lenox, Massachusetts
The Berkshires are a year-round destination, each season offering its unique charm. However, if you’re keen on theater, music, and other events, summer is the ideal time to visit. If your heart flutters at the sight of vibrant fall foliage, plan your trip for early to mid-October, when the leaves are at their peak.
I enjoyed my springtime visit to the Berkshires, with lots of flowers and delightful partly cloudy skies (though honestly, Massachusetts can be quite hit or miss in the spring months with lots of gray days). Winter is very quiet, and not all the attractions will be open,
Is Lenox worth it?
Of course Lenox is worth it — and if you time your visit for Tanglewood, even better! Even so, I think you can get away with simply having Lenox be one day out of a longer Berkshires itinerary. There are so many wonderful things to do here.
I hope you have the best time on your trip to Lenox!
More on the Berkshires:
- 33 Best Things to Do in the Berkshires, MA
- Best Towns in the Berkshires, MA
- 12 Fun Things to Do in Stockbridge, MA
More on Massachusetts:
- Where to Stay in Boston: Hotels, Neighborhoods & More!
- 40+ Fun Things To Do In Boston At Night
- Best Time to Visit Boston
- What NOT to Do in Boston
- The Best Museums in Boston
- 25 Historic, Spooky Things To Do in Salem, MA
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- 24 Cool Things To Do in Cambridge, MA
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- 22 Fabulous Things to Do in Provincetown, MA
- Which Of The 6 Martha’s Vineyard Towns Is Best For You?
- A Guide to Oak Bluffs, MA — Home of the Gingerbread Houses
- A Guide to Edgartown, MA — Prettiest Martha’s Vineyard Town
- A Guide to Vineyard Haven, MA — Authentic Town on Martha’s Vineyard
Have you been to Lenox? Have any tips to share?