Why we love The Berkshires
• The charming towns of Lenox and Stockbridge.
• Fall foliage like you’ve never seen it.
• Wellness and art and farmstands.
When many people think of the Berkshires—a lush region that hugs the western border of Massachusetts—they think of opulent mansions and refined cultural festivals. Sure, there’s all that, but here at The WeekEnder we’re also in love with the farmstands, the country inns, the rustic-chic restaurants, the wellness spas, and some of the best leaf peeping in the country, if not the world.
We’ve explored other parts of The Berkshires in past issues, including cool North Country and the hip town of Great Barrington. This weekend, join as we escape to the heart of the Berkshires—the towns of Lenox and Stockbridge—to experience fall in all its glory.
 Sarah Eustis (L), Vic Cappadona (C), Mary and Ben Daire (R)
Sarah Eustis’s family has deep roots in this area: Her grandparents bought Stockbridge’s iconic Red Lion Inn in 1968. Sarah moved away for a bit but was drawn back by the area’s charms and now runs the family business, Main Street Hospitality, which has grown to include a number of boutique hotels across New England. “What I love is that there’s an artistic, intellectual, bohemian energy in these hills balanced with generations of old families who’ve been coming here since the turn of the century and have brought a lot of resources and energy,” she says.
This part of the Berkshires is also known for its wellness heritage, which goes back to the 1960s with the founding of the yoga retreat, Kripalu, and has continued with spas like Canyon Ranch and Miraval, which just opened this summer. “The Berkshires is such a renowned destination for wellness—the perfect quiet escape from Boston and New York City,” says general manager Vic Cappadona. “It’s a place where people can reconnect with themselves and their natural surroundings.”
This area also has a thriving artisanal culinary scene, which husband-wife team Ben and Mary Daire celebrate at Dare Bottle Shop & Provisions in Lenox. The new shop showcases the craftsmanship of the Berkshires—from organic wines and craft beers to small food producers and makers—as well as finds from around the globe. The couple honed their food-and-wine chops in France, but decided to settle down here. “Lenox is such a great village and what brings it to the next level is the caliber of the restaurants and the music scene and the art,” says Mary. “It’s also a pedestrian playground where you can slow down and connect.”
Who doesn’t want to slow down for the weekend? Let’s head for the hills.
-Laura Begley Bloom, New York's Senior WeekEnder Writer
Map of the area
1. Bartlett’s Orchard
2. Pleasant Valley Wildlife Sanctuary
3. Olivia’s Overlook
4. Parsons Marsh Reserve
5. Dare Bottleshop & Provisions
6. Wheatleigh
7. Miraval Berkshires
8. The Mount
9. High Lawn Farm
10. Norman Rockwell Museum
11. Naumkeag
12. The Red Lion Inn
Where to stay
 The Red Lion Inn
From tranquil inns to spas with luxe treatments, the hotel options are endless in Lenox and Stockbridge.
For history buffs: The Red Lion Inn in Stockbridge - This historic landmark property is a town centerpiece with rooms spread across several buildings, from the white colonial main inn to the Maple Glen house (a great choice for guests looking for a more modern country experience). The Lion’s Den—a former speakeasy—just reopened as a swank cocktail bar.
For sweethearts: Seven Hills Inn in Lenox - A farmhouse originally built in the 1700s by early Massachusetts colonists has been transformed into an inn surrounded by 27 acres of gardens. Request a suite with an in-room fireplace in the Carriage House or the Manor House.
For luxury lovers: Wheatleigh in Lenox - This extravagant country-house hotel with Tiffany windows and other lavish details was designed to look like a palazzo in Florence.
For foodies: The Whitlock in Lenox - Originally built in 1771 by a farmer who turned his two-room farmhouse into an inn for stagecoach travelers, the property has taken that heritage to the next level with Ophelia’s, a farm-to-table restaurant that features herbs and garnishes from local purveyors.
 Wheatleigh (L), Miraval Berkshires (R)
For socializing with the locals: Apple Tree Inn in Lenox - A favorite for drinks, dinner, and a lively music scene. “Antonio, the bartender, makes delicious drinks—I recommend his African Flower—and sets a warm and welcoming vibe that makes it easy to relax,” says Rich Montone, director of development at the Berkshire Natural Resources Council.
For design enthusiasts: Cornell Inn in Lenox - A trio of 18th- and 19th-century houses have undergone a massive facelift courtesy of The Kaleidoscope Project, a nonprofit dedicated to highlighting diversity in interior design. The organization brought in 23 BIPOC designers and numerous home brands to refresh the 28 rooms
For shoppers: 33 Main in Lenox - With interiors by Annie Selke, a well-known design guru, this chic inn delivers the experience of a B&B with the modern amenities of a luxury hotel. Annie’s boutique, right across the street, sells amenities from the inn.
For Instagrammers: Miraval Berkshires in Lenox - Set on 380 acres designed by Central Park landscape architect Frederick Law Olmsted, Miraval dazzles with acclaimed designer Clodagh’s transformation of an 1894 mansion. Miraval is all about life in balance, so in addition to top-notch health programming, you can indulge with experiences like cocktail classes and oyster-shucking lessons.
For health nuts: Canyon Ranch Lenox - This world-class wellness resort is set in the historic Bellefontaine mansion, which was once home to aristocrats during the gilded age. The building houses a health and healing center, in addition to extensive spa programming, daily fitness classes, and lectures in well-being.
For yogis: Kripalu in Lenox - North America’s largest yoga retreat center is a crunchy spot for wellness seekers in search of everything from energy healing to Kripalu’s signature R&R (retreat + renewal) program that combines Ayurvedic wisdom and guided outdoor experiences.
Where to eat
The quality of the restaurants in Lenox and Stockbridge is stellar, but a tip from Rich Montone, director of development at the Berkshire Natural Resources Council: “Lenox and Stockbridge are popular, so if you try to walk into a restaurant at 7 p.m. on a Saturday night without a reservation, you’ll be out of luck.”
Best breakfasts
 Haven
Haven in Lenox - Healthy bites to start the day with ingredients sourced from nearby organic farmers, as well as environmentally conscious distributors.
Patisserie Lenox in Lenox - French pastries that are the next best thing to being in France.
Lenox Coffee in Lenox - “A long-standing tradition for locally brewed coffee,” says Mary Daire.
Lunchtime
 The Olde Heritage Tavern (L), Shots Cafe (R)
The Olde Heritage Tavern in Lenox - There’s usually a line out the door at this neighborhood hotspot; come at lunch to avoid the crowds and don’t miss the pulled pork, a fan favorite.
Shots Cafe in Lenox - This area has a proliferation of European-style cafes: This is the place to go for ham-and-gruyere croissant sandwiches and more.
The Lost Lamb in Stockbridge - A Le Cordon Bleu-trained chef opened this French-style pâtisserie known for its baguette sandwiches.
Loeb's Foodtown in Lenox - “The local secret,” says Mary. “It’s a great stop for picnic supplies like sandwiches and potato salad.”
Casual bites
 Frankie's Ristorante Italiano
Brava in Lenox - A Wine Spectator Award-winning bar with a menu of globally inspired tapas, from smoky patatas bravas to Boom Boom Shrimp with sweet Thai chili sauce.
Frankie’s Ristorante Italiano in Lenox - A red checkered spot owned by Mary Daire’s sister, with chicken piccata just like your Italian mama used to make.
Pizzeria Boema in Lenox - Frankie’s sister restaurant. “The kind of authentic pizza experience that you’d get in Naples, with a Neapolitan-style oven,” says Mary.
Date night
 Bistro Zinc (L), Alta Restaurant & Wine Bar (R)
Bistro Zinc in Lenox - A sleek neighborhood bistro that does all the classics just right (moules frites, Boeuf Bourguignon) and doubles as an art gallery.
Alta Restaurant & Wine Bar in Lenox - Farm-to-table dining with a Mediterranean twist (quinoa salad with mint vinaigrette, seared duck breast with salty caramel sauce) and 24 wines by the glass.
Firefly in Lenox - “A beautiful horseshoe bar in the center of the room, outstanding craft cocktails and thoughtfully prepared, locally sourced food in a setting that often features live music later in the evening on the weekends,” says Rich.
Sweets
 Sweet Dreams
Sweet Dreams in Lenox - Dozens of flavors of organic ice cream made with fresh ingredients from local producers, plus treats baked right onsite.
What to do
Leaf peeping
 Parsons Marsh Reserve
The Berkshire Natural Resources Council is dedicated to helping preserve this region’s natural beauty and also has a handy app with trail maps. We got Rich Montone, director of development, to share a few great locations for fall foliage—though the truth is that you’re likely to spot the changing colors everywhere. “The access to the outdoors is remarkable here,” says Rich. “So truly, it doesn’t matter where you go in autumn—wherever you are, you’ll find some beauty.”
Parsons Marsh Reserve in Lenox - “An easy place to see spectacular fall foliage. It is a hard pack trail and boardwalk that was designed specifically for people who want to use strollers or wheelchairs.”
Olivia’s Overlook in West Stockbridge - “There are several outlooks along this trail, but even the parking lot is an amazing place to have a picnic and snap a photo of the reds and golds and oranges and yellows.”
Kennedy Park in Lenox - “A popular place right in town where you can get outside and take in the autumn colors.”
Pleasant Valley Wildlife Sanctuary in Lenox - “A Mass Audubon site with a wide range of trails.
Historic homes
 The Mount
In the late 1800s, some of America’s wealthiest families built massive estates in the Berkshires—and lucky for us, many are now open to the public.
The Mount in Lenox - This literary hub is the former home of Edith Wharton (author of The Age of Innocence). There are a number of house tours—including one from the POV of her servants and a popular ghost walk—plus author lectures, theater performances, jazz evenings, and outdoor sculpture exhibits.
Ventfort Hall in Lenox - A Jacobean Revival-style mansion built in 1893 for the sister of J. P. Morgan is now home to the Museum of the Gilded Age, where you can learn all about the life, industry, and society of that time.
Naumkeag in Stockbridge - This McKim, Mead & White-designed summer retreat has elegant gardens, a rare Berkshire cottage, and a not-to-be-missed fall pumpkin festival.
Chesterwood in Stockbridge - The summer home of sculptor Daniel Chester French (who designed the statue of Abraham Lincoln in Washington, D.C.’s Lincoln Memorial) is a must-visit for fans of 20th century art.
Frelinghuysen Morris House in Lenox - The former home of abstract artists George L.K. Morris and Suzy Frelinghuysen has been transformed into a museum where you can see their collection of modernist furniture and art from Fernand Leger to Picasso.
Arts and culture
 Norman Rockwell Museum (L), TurnPark Art Space (R)
Lenox and Stockbridge are home to a rich arts scene that spans the gamut. Performances, paintings, sculpture—whatever you’re looking for, you’ll find it here.
Norman Rockwell Museum in Stockbridge - Iconic artist Norman Rockwell moved to Stockbridge later in life. This museum houses the world’s largest collection of his drawings and paintings.
Berkshire Botanical Garden in Stockbridge - One of New England’s oldest public gardens has 15 acres filled with thousands of exquisite varieties.
TurnPark Art Space in West Stockbridge - At this seven-acre outdoor sculpture garden, you can catch live music, contemporary theater, nature workshops, film screenings, and more. Pro-tip: It’s also a great place for a picnic.
Shakespeare & Company in Lenox - Storytelling at its finest. While it’s primarily a summer attraction, there are still a few shows through the fall.
Tanglewood in Lenox - The Boston Symphony Orchestra’s performances are done for the season, but put Tanglewood on your radar for a summer visit.
Farms
 Hilltop Orchards
From vegetable to fruit to dairy farms, the offerings in the Berkshires are vast. These are our top spots for fall.
Bartlett’s Orchard in Richmond - Pick-your-own apples, cider, produce, and more. “The best cider donuts on the planet,” says Mary Daire.
Hilltop Orchards in Richmond - Hayrides, live music, full-moon walks, and award-winning bottles from the onsite Furnace Brook Winery.
High Lawn Farm in Lee - Pet the cows, sample the world’s best eggnog, and don’t miss the amazing ice cream. “The luckiest cows on the planet are pastured there,” says Mary. “For a sweet treat, it’s the place to go for the most local-to-the source ice cream that you could hope for.”
Shopping
 Dare Bottleshop and Provisions (L), Sohn Fine Art (R)
This is an exciting shopping destination, thanks to retailers who value craftsmanship and individuality. Here’s a sampling.
Dare Bottleshop and Provisions in Lenox - This cutting-edge wine, beer, and food retailer is about to celebrate its one-year anniversary. Look for a new line of dinner and party accessories. What is co-owner Mary Daire is excited about right now? “I’m loving our full-bodied roses that are juicy and perfect to pair with fall food,” she says.
The Bookstore in Lenox - Part bookstore, part literary salon, and part gathering place at the (hilariously named) Get Lit Wine Bar.
Sohn Fine Art in Lenox - A photographer started this gallery that specializes in contemporary photography and art, if you want to bring a piece of the Berkshires home with you.
Heirlooms Jewelry in Stockbridge - A family-owned boutique with antique and estate jewelry from close to home and around the globe.
Casablanca in Lenox - Contemporary fashions with a unique point of view.
Getting there
It’s about two-and-a-half hours from Midtown Manhattan to Lenox. For more info on the Berkshires, check out berkshires.org.
Pit stop
Calling all foodies: Rubiner’s Cheesemongers & Grocers, in nearby Great Barrington, serves up more than 125 different kinds of cheese.
Listen
Hello Bookstore - Streaming on Apple and Amazon Prime, this documentary tells the story of The Bookstore owner Matthew Tannenbaum, who has been called “the Living Legend of Lenox.” |
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