I’ve Lived on the East Coast My Whole Life—and I Think This Charming Small Town Is the Best Place to See Fall Foliage

In the heart of the Berkshires, Lenox, Massachusetts, manages to feel both low-key and culturally rich.

Its biggest claim to fame is Tanglewood, the Boston Symphony Orchestra’s summer home, which draws audiences for a wide range of performances, from classical concerts to popular guest artists. Theater lovers, though, often head to Shakespeare & Company, a long-running festival with a busy calendar of plays, while readers and history buffs make time for The Mount, Edith Wharton’s former estate. All of this, of course, becomes even more magical in the fall, when the town is bathed in hues of gold, crimson, and ochre.

Lenox has also become a destination for wellness getaways, thanks to two well-known retreats: Canyon Ranch and Miraval Berkshires. Both properties—recognized for their spas in Travel + Leisure’s 2025 World’s Best Awards—have adults-only, all-inclusive programs that blend fitness, mindfulness, nutrition, and spa treatments. They’re popular spots for East Coast travelers looking to reset.

Outdoor activity options also abound in the area. Here, you can hike nearby trails, boat on quiet lakes, or simply take in the scenery on a drive through the hills. But if you’re more interested in seeing what’s downtown, there are plenty of boutique shops, local restaurants, and a mix of cozy inns and polished hotels. Regardless, whether you’ve come for the music, a restorative retreat, or fresh mountain air, this little town makes it easy to slow down and be present.

Here’s what you need to know before planning a trip to Lenox, Massachusetts.

Best Hotels & Resorts

Miraval Berkshires

According to Berkshires-based Fora travel advisor Janine Yu, this 121-room, adults-only, all-inclusive property has an “impressive program of classes, activities, and workshops,” including beekeeping, equine therapy, and aerial yoga. Between activities, guests can indulge in farm-to-table fare or unwind in the 29,000-square-foot Asian-inspired spa, which was voted one of the best in the country in the country in T+L’s 2025 World’s Best Awards. “A stay here will help you pause, reflect, and explore interests you may not have known you had, all in a luxurious and bucolic setting,” says Yu.  

Canyon Ranch Lenox 

The 126-key Canyon Ranch Lenox stands out for its World’s Best Awards-winning spa and fitness center, which spans some 100,000 square feet. Here, guests can partake in over 150 wellness offerings ranging from yoga and meditation to high-intensity workout classes and nutrition workshops. Beyond the spa, guests are encouraged to get outside and explore the stunning surroundings via guided hikes, biking, kayaking, snowshoeing, and cross-country skiing, depending on the season. 

Stonover Farm

A favorite of Yu’s, this luxury inn feels like it’s been plucked straight out of a design magazine, with curated antiques, contemporary furnishings, and artful details. The 130-year-old farmhouse-turned-bed-and-breakfast has five accommodations—three suites, a cottage, and a converted schoolhouse. The 10-acre grounds are just as picturesque as the interiors, with lush trees, expansive lawns, and a spring-fed duck pond. Amenities include complimentary breakfast—best enjoyed in the outdoor courtyard—an intimate bar, and a cozy library.

The Cornell Inn

The Cornell Inn is set across three historic buildings—one dates back to 1777—and has 28 individually decorated, antique-filled rooms. Some are outfitted with fireplaces, kitchenettes, or private patios, while others showcase cozy sitting areas and charming period details. Mornings begin with a complimentary gourmet breakfast. After, guests can stroll the landscaped grounds or settle into an Adirondack chair on the wraparound porch.

33 Main

The brainchild of home furnishings entrepreneur and Lenox resident Annie Selke, 33 Main feels like a home catalog come to life, with chic textiles and vibrant design accents. Each of the eight guest rooms is distinctively designed to showcase Selke’s signature aesthetic—think bold patterned wallpaper, crisp linens, and one-of-a-kind upholstered headboards that double as statement pieces. Rooms also feature Hästens mattresses for a supremely restful night’s sleep. The amenities are just as thoughtful: complimentary daily breakfast, fresh-baked goods, and a nightly cocktail hour in the front parlor, which makes the inn feel as convivial as it is stylish.

Best Things to Do 

The Mount

The Mount, the 1902-era former home of Pulitzer Prize–winning author Edith Wharton, is a historic house museum and cultural center that gives visitors a glimpse into her world through restored rooms and rotating exhibits. Lu especially recommends exploring the grounds, which are as captivating as the house itself, with elegant formal gardens and wooded trails for scenic strolls.

Ventfort Hall Gilded Age Mansion & Museum

Built in 1893 for Sarah Morgan, the sister of financier J.P. Morgan, Ventfort Hall Gilded Age Mansion & Museum once stood among Lenox’s grand “summer cottages.” Today, visitors can wander through its soaring great hall, wood-paneled library, and ornate dining room. Rotating exhibits, lectures, and theatrical performances help bring the storied house and its history to life.

Tanglewood

Tanglewood shines brightest in the summertime, when the Boston Symphony Orchestra takes up residence, making it well worth a visit, says Lu. But the calendar doesn’t end there: the beloved Berkshires venue also hosts lectures, chamber music, and special concerts into the fall, drawing culture-seekers year-round. However, the grounds are stunning in every season, with sweeping lawns, shaded groves, and views of the Berkshire Hills.

Elm Court

Designed in 1885 as a summer retreat for Emily T. Vanderbilt and her husband, William D. Sloane, Elm Court is the largest shingle-style home in the United States. It’s also one of the few remaining historically significant Gilded Age mansions in the Northeast, including the aforementioned Ventfort Hall. The 89-acre estate also has grounds planned by Frederick Law Olmsted, the landscape architect behind New York City’s Central Park and the U.S. Capitol.

Mass Audubon’s Pleasant Valley Wildlife Sanctuary

Spanning more than 1,000 acres, Mass Audubon’s Pleasant Valley Wildlife Sanctuary is an excellent destination for hikers and birders of all ages and experience levels. The sanctuary’s vast network of trails winds through forests, meadows, and wetlands, as well as up the slopes of Lenox Mountain. Along the way, visitors may spot signs of the sanctuary’s most visible resident, the beaver, from impressive dams to cleverly constructed dens and lodges, as well as birds such as the snow goose, lapland longspur, and chimney swift.

Best Shopping

What A Gift

For home décor and housewarming gifts of every kind (and we won’t tell if you’re shopping for yourself) make a beeline for What A Gift. Tucked in the heart of downtown, this shop is nothing short of charming with its selection of candles, fragrances, throw pillows, and even cards and gratitude journals.

Home On Main

Home on Main has a curated selection of (you guessed it) home goods. The stylish storefront is filled with a slew of thoughtfully chosen pieces designed to bring comfort and character into your space. Expect everything from designer rugs and plush linens to handcrafted bamboo bowls and local artwork. You’ll also find trinkets perfect for gifting, such as fragrances, candles, scarves, and robes.

Casablanca

For designer duds, don’t miss Casablanca, which is stocked with luxe pieces from brands like Max Mara, Robert Graham, Missoni, and more. Both men and women will find a range of fashion-forward options here, with a wide selection of clothing—think button-down shirts, dresses, and sweaters—alongside accessories like belts and scarves.

Shooz

A sister store to Casablanca, Shooz is conveniently located right down the street and is filled with fun shoes. Alongside fashion-forward footwear, you’ll also find bags from designers like MZ Wallace, plus a selection of chic casual clothing.

The Bookstore and Get Lit Wine Bar

This cozy independent bookstore has been a Lenox staple for over 40 years. Expect a well-curated mix of fiction and nonfiction for adults, plus a standout selection of cookbooks and children’s titles. After browsing the shelves, settle in at its aptly named wine bar, Get Lit, where good reads meet good pours.

Best Restaurants 

Frankie’s Ristorante

Frankie’s Ristorante channels the charm of an old-school Italian, red-sauce joint, with dimly lit interiors and a hearty menu of classics. Open exclusively for dinner, it draws both travelers and locals for specialties like eggplant parm, spaghetti carbonara, and fried calamari. The drinks list spans wine and beer, and includes colorful cocktails such as the Purple Rain, a gin-based libation, while desserts range from tiramisu and cannoli to creamy gelato. For plant-based diners, there’s even a separate vegan menu.

Alta Restaurant & Wine Bar

For “a refined, Mediterranean-inspired dinner,” Yu recommends snagging a table at Alta Restaurant & Wine Bar downtown. This dinner-only spot showcases local, organic ingredients across a menu that ranges from herb-roasted cod and quinoa salads to beer-braised pork and foie gras terrine. The wine list is equally impressive, with selections from around the world. If the weather allows, dining al fresco is a treat; otherwise, the cozy, intimate dining room sets the scene indoors, while the lively bar has a more laid-back atmosphere.

Shots Cafe

This local-loved haunt is a personal favorite for its fresh-baked pastries, savory quiches, and creative coffee concoctions, like the mint chocolate chip lattes. Beyond breakfast, it serves some of the best quesadillas, salads, and sandwiches in town, and even has beer and wine for those lingering into the afternoon.

Bistro Zinc 

Step inside Bistro Zinc and you’ll feel like you just entered a chic Parisian brasserie, complete with a zinc-topped bar and dining rooms with mosaic floors. Indulge in staples like French onion soup, moules-frites, and beef bourguignon, paired with classic cocktails such as a French 75 or a pear martini. Alternatively, you can order a glass from the curated wine list that features France and beyond.

Antimony Brewing

“Antimony Brewing is a fun craft brewery with an eclectic menu,” says Lu. For something adventurous, she recommends ordering one of the burgers made from game meats, such as elk or bison, although there are also familiar options like wagyu or lamb. In addition to an array of handhelds, expect plenty of elevated pub fare, including cheese curds and wings, poutine, and giant pretzels served with cheese and honey mustard. Rounding out the experience, the brewery frequently hosts live music, making it a lively hangout spot.

Best Time to Visit

While Lenox, Massachusetts, shines in all four seasons, the town truly shines in the fall, when the maples, oaks, and birches in the area turn fiery colors. There are also a number of autumn festivals that travelers can take part in, including the Lenox Apple Squeeze (a celebration of all things to do with apples) and the Naumkeag Pumpkin Show, which takes place in nearby Stockbridge, Massachusetts, about a 10-minute drive away.

Summer is also another popular time to visit, when crowds flock to Tanglewood’s sprawling grounds for al fresco picnics on the lawn that pair perfectly with evening performances of the Boston Symphony Orchestra under the stars. Summer also ushers in Shakespeare & Company‘s lively plays, adding a dose of drama (pun intended) to the season.

How to Get There

Lenox is within easy driving distance of major cities, such as New York City (about 145 miles away) and Boston (130 miles). If you’d rather fly, Albany International Airport (ALB) in New York and Bradley International Airport (BDL) near Hartford, Connecticut, are both around an hour away from Lenox by car. Pittsfield Municipal Airport (PSF) in nearby Pittsfield, Massachusetts, is just six miles from Lenox, but there are limited flights.

Trains are another option, with Amtrak offering seasonal weekend service on the Berkshire Flyer from New York City to Pittsfield from June to September, but regardless of how you arrive, having a car makes it much easier to explore Lenox and the region’s eclectic towns at your own pace.

How to Get Around

Downtown Lenox itself is charming, compact, and entirely walkable, with tree-lined streets, boutique shops, cafés, and galleries that are easily accessible on foot. However, if you’d like to explore the broader area, having a car is a great option. There’s also the Berkshire Regional Transit Authority, which connects Lenox to nearby towns like Pittsfield, Stockbridge, and Great Barrington. While routes are limited and there’s no Sunday service, it’s currently free to ride through 2026—a budget-friendly way to hop between cultural stops and small-town main streets without worrying about parking.