How to Spend a Weekend in the Berkshires
Art museums, boutique wineries, cideries and cozy inns await in the Berkshires.
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Rolling hills, fiery foliage and winding country roads make the Berkshires one of New England’s most charming weekend escapes. Just a two-and-a-half-hour drive from Boston and three from New York City, the region (encompassing parts of western Massachusetts and northern Connecticut) has long been a favorite escape for urbanites eager to swap honking horns and crowded sidewalks for crisp mountain air and rolling hills. The locale's small towns each offer distinct personalities: Williamstown with its world-class art museums, North Adams with its industrial edge and MASS MoCA, Lenox with its boutique-lined streets and Tanglewood concerts, and Stockbridge with its postcard-worthy Main Street, immortalized in Norman Rockwell's Stockbridge Main Street at Christmas.
The Berkshires is a true year-round vacation destination, but fall just may be its finest hour. Hillsides burn with reds and golds, orchards brim with apples ready for picking, and cultural programming is in full swing. Festivals and community events, from the Lenox Apple Squeeze to the FreshGrass Festival, only add to the region’s seasonal charm.
A long weekend in the Berkshires offers something for everyone: a morning hike up Mount Greylock, where fiery foliage stretches across five states; an afternoon apple-picking and cider-tasting at a local orchard and an evening in Lenox, whether that means lingering over a farm-to-table dinner with local wine or catching off-season programming at Tanglewood. Read on for the best places to stay, eat and explore on a Berkshires getaway.
How to Plan a Weekend Getaway to the Berkshires: The Ultimate Travel Guide
Where to Stay
Canyon Ranch Lenox
- 165 Kemble St, Lenox, MA 01240
Housed on a historic 120-acre estate, Canyon Ranch Lenox is an all-inclusive wellness retreat that shines especially bright in autumn, when the landscape transforms into a blaze of reds, oranges and golds. Guests can fill their days with scenic hikes, forest bathing, cycling or yoga under the changing leaves before unwinding at the spa, a 100,000-square-foot sanctuary with seemingly endless treatments, a fitness center, an indoor pool and hydrotherapy experiences. The programming is equally impressive, with classes ranging from Pilates and barre to meditation and breathwork. Between activities, guests dine on gourmet, chef-crafted meals featuring seasonal ingredients (think chicken farro salad with crisp Granny Smith apples, burgers with house-made potato rolls, omelets with fresh-picked vegetables and artisan-baked breads), or retreat to one of the 126 rooms.
This fall also brings something new to the getaway: outdoor treatment tents where guests can book Reiki, reflexology and other therapies as they bask in the brisk mountain breeze. A handful of themed retreats, like the Berkshires Fall Foliage Escape, make the case for planning a visit before the last leaves fall.
Red Lion Inn
- 30 Main St, Stockbridge, MA 01262
Dating back to 1773, the Red Lion Inn is one of the Berkshires' most storied landmarks. With its white clapboard exterior and expansive rocking chair-lined porch, the inn anchors the small town of Stockbridge like something out of a Norman Rockwell painting. (Fittingly, his former studio, part of the Norman Rockwell Museum, is just down the street.) Inside, the inn leans into its colonial-era character. Expect narrow hallways creaking beneath wide-plank floors and walls adorned with patterned wallpaper, oil paintings and antique clocks. The same aesthetic extends to the 108 rooms and suites, most of which are attired with patterned wallpaper, four-poster beds and floral drapery.
Beyond the porch, a flora-filled courtyard serves as another central gathering spot for sipping coffees or cocktails. The main dining room serves classic regional fare (don't miss the New England clam chowder) in an elegant, chandelier-filled setting outfitted with lavish red drapery and printed wallpaper. The casual downstairs tavern, reminiscent of an old English pub, offers ice-cold brews, hearty sandwiches and salads. Tucked even deeper below street level, the aptly named Lion's Den speakeasy serves handcrafted cocktails and bar bites like charcuterie and smashburgers, and regularly hosts live music acts.
Tourists
- 915 State Rd, North Adams, MA 01247
In North Adams, just down the road from the galleries of Mass MoCA, sits Tourists, a 1960s motor lodge reimagined as an arty boutique retreat. Its design strikes a balance between rustic and hip, with cedar-clad exteriors and interiors—including 46 guest rooms and common spaces—that balance natural wood and warm textiles with vintage accents and pared-back furnishings. At the heart of the property, the main lounge glows around a roaring fireplace, flanked by vintage rugs, low-slung chairs and sofas layered with wool blankets. The riverfront getaway extends into an 80-acre forest campus dotted with sculptural installations and tranquil nooks, all linked by a striking suspension bridge. Housemade breakfast staples, such as brown-butter waffles, smoked salmon-topped bagels and gochujang cheddar scones, fuel days of museum-hopping or leaf-peeping.
Miraval Berkshires
- 55 Lee Rd, Lenox, MA 01240
Set on 380 acres in Lenox, Miraval Berkshires takes a more free-spirited approach to wellness than its neighbor, Canyon Ranch. The programming here blends curiosity and adventure. For example, mornings might begin with aerial yoga or ziplining through the trees, while afternoons could feature beekeeping workshops, equine therapy or a reflective walk through the meditation labyrinth. When the weather cooperates, the outdoor pool becomes a sparkling centerpiece, framed by flowers and towering trees. Like the rest of the resort, the 121 guest rooms and cottages evoke a sense of serenity with clean lines, soothing tones, natural woods and oversized windows that let in loads of natural light.
The true star of the show is the Asian-inspired Life in Balance Spa, where treatments range from Ayurveda and Reiki to Thai massage and energy work. That global influence carries into the kitchen as well, with menus featuring saffron-lemon risotto, wild-mushroom rice bowls finished with local kimchi, and lion's mane tacos.
What to Do
Tanglewood
- 297 West St, Lenox, MA 01240
Best known as the summer home of the Boston Symphony Orchestra, Tanglewood draws music lovers from across the country. Summer is the busiest season, with big-name concerts and picnics spread across the lawn. In the fall, the atmosphere shifts. While the crowds have thinned, the programming continues, with concerts, recitals and guest lectures keeping the calendar full. Even without an event, the grounds are worth visiting for their wide-open fields and scenic walking paths.
The Mount
- 2 Plunkett St, Lenox, MA 01240
The Mount, Edith Wharton's former estate in Lenox, is a National Historic Landmark and a vivid reflection of the writer's imagination, from its stately interiors to its sweeping terraces. Wharton designed the house and gardens herself in 1902, calling it her "first real home." Today, the estate is best described as part museum, part outdoor escape. Visitors can step back in time with a guided tour through grand drawing rooms, roam through the lush, European-inspired gardens or wander along wooded trails that open onto breathtaking hillside views. Additionally, in nearby Pittsfield, literary lovers mustn't miss Arrowhead—the home-turned-museum where Herman Melville penned Moby Dick.
Lakeview Orchard
- 94 Old Cheshire Rd, Lanesborough, MA 01237
Perched in the rolling hills of Lanesborough, Lakeview Orchard offers a farm-to-table experience. Visitors can pick their own fruit—cherries in early July, raspberries and currants by mid-summer, blueberries through August, and apples once September arrives. Apple season marks the start of fresh cider, pressed on-site from the orchard's own harvest. Beyond the fields, the bakery keeps visitors well-fed with scratch-made treats, including fan favorites like still-warm cider donuts plus a seasonal selection of fruit pies, turnovers, scones and whoopie pies.
Hilltop Orchards
- 508 Canaan Rd, Richmond, MA 01254
Hilltop Orchards is part cidery, part winery and part outdoor playground. You can sip your way through a flight of Johnny Mash ciders, from classic New England styles to unexpected flavors like coconut lime. Book a tour to see the process up close, from apples pressed on the old-fashioned rack-and-cloth to cider aging slowly in oak barrels. Alternatively, savor one of the dozen-plus artisanal wines made right on-site.
The orchard isn't just about drinking, though. Trails designed by John Morton loop through the property, winding past rows of apple trees and into the woods. Hike them in spring, summer and fall or snowshoe them in winter. Back at the farm, sit back and relax in an Adirondack chair with your drink of choice—best enjoyed with a hot apple cider donut.
Mass MoCA
- 1040 Mass MoCA Way, North Adams, MA 01247
Housed in a converted mill complex in North Adams, the Massachusetts Museum of Contemporary Art spans roughly 250,000 square feet across a constellation of brick buildings—an ideal setting for some of the most ambitious (and largest) contemporary art in the United States. An entire building is devoted to the Sol LeWitt wall-drawing retrospective, which covers nearly one acre of interior wall space. The museum also has large-scale installations by artists like James Turrell, including immersive light environments. Beyond the galleries, the experience extends into performing arts, with concerts, experimental theater, film screenings and even an annual bluegrass festival unfolding across its industrial courtyards and venues.
Mount Greylock State Reservation
- 30 Rockwell Rd, Lanesborough, MA 01237
At 3,491 feet, Mount Greylock stands as Massachusetts' highest peak and one of the Berkshires' most beloved landmarks. On a clear day, the summit rewards you with sweeping views across five states: Massachusetts, New York, Connecticut, Vermont and New Hampshire. Trails here run the gamut from leisurely woodland strolls to steep, rocky climbs that may leave your legs sore, though the views are more than worth it. Come autumn, the ridgelines blaze with fiery reds and golds, making Mount Greylock one of New England's most spectacular spots for leaf-peeping.
Where to Eat and Drink
Berkshire Mountain Distillers
- 356 S Main St, Sheffield, MA 01257
Equal parts educational and convivial, Berkshire Mountain Distillers in Sheffield creates small-batch, award-winning spirits, from gin and bourbon to one-off experimental blends. Sample a tasting flight or settle in with a seasonal cocktail in the tasting room. If you're curious about the craft, self-guided tours offer a behind-the-scenes look at the distilling process. When you're done, it's worth sticking around to explore the campus and wander the grounds, sip cocktails beneath the covered pavilion or cozy up by the fire pit.
Casita
- 1111 Mass MoCA Way, North Adams, MA 01247
Just steps from the MASS MoCA galleries, Casita is the kind of spot you wander into for a quick bite and somehow lose track of time. The menu is filled with playful riffs on Mexican staples, spotlighting ingredients sourced from local farmers, cider makers and fishermen. Mushroom empanadas arrive draped in pistachio mole, while street corn shows up in the form of pillowy gnocchi. Libations are mezcal-forward, with smoky cocktails that pair as easily with a plate of tacos as with a lingering conversation. There's also a thoughtful lineup of natural wines and local beers. The vibe is relaxed but buzzy; a place where museum-hoppers and North Adams regulars trade stories across the same table, margaritas in hand.
Shots Cafe
- 27 Housatonic St, Lenox, MA 01240
In the heart of historic downtown Lenox, Shots Café is a go-to for a laid-back breakfast or lunch. With its central location and cozy, welcoming vibe, it's the kind of place you'll duck into more than once during a Berkshires stay. The menu covers the essentials (egg sandwiches, savory salads, hearty paninis), but the real draw is the pastry case. Expect a rotating selection of treats, including flaky croissants, chocolate éclairs and muffins coupled with savory selections like fresh-baked, veggie-loaded quiches, best enjoyed with a cappuccino or latte.
Dairy Cone
- 197 Tyler St, Pittsfield, MA 01201
Sometimes it's the simplest spots that hit the sweetest note. Dairy Cone is a no-frills, family-run ice cream joint that has been slinging out frozen treats for decades, and it's easy to see why. Go classic with vanilla or chocolate soft serve, or savor local favorites like black raspberry and coffee. The rainbow swirl (pictured) is tough to pass up, and it's every bit as tasty as it is photogenic. Rounding out the menu are treats like fruity Dole Whip, frozen yogurt, over-the-top sundaes and extra-thick milkshakes.
Balderdash Cellars
- 81 State Rd, Richmond, MA 01254
The family-owned Balderdash Cellars is as much a neighborhood hangout as it is a working winery. Guests gather on the lakefront lawn to sip wine, linger over conversation, and take in the views, especially in the fall, when the trees surrounding the lake burst into vibrant colors. Adirondack chairs and picnic tables dot the grass, and with no reservations required or accepted, the whole place carries a relaxed, come-as-you-are vibe. Live music and food trucks often round out the scene, giving it more of a backyard feel than a formal tasting room. The wines (whites, rosés and reds) have cheeky names, such as the "Truth Serum" chardonnay and "Liquid Courage" cabernet sauvignon.
Frankie's
- 80 Main St, Lenox, MA 01240
This cozy Italian eatery in downtown Lenox leans into classic Italian-American comfort, from the red-and-white-checkered tablecloths and dim lighting to the warm, attentive service. The menu is loaded with old-school favorites like chicken parm, seafood fra diavolo and lasagna, all made with a Berkshires twist thanks to locally sourced ingredients. The drink list includes wine, beer and creative cocktails like the aptly named "Under the Tuscan Sun" (tequila with lime, grapefruit bitters, cilantro simple syrup, and a Tajín rim). A full vegan menu ensures everyone at the table is covered.
