Your Curated Berkshires Guide
Live the Berkshires
Like a Local
Handpicked by our team — the finest tables, hidden trails, living rooms of culture, and everything that makes this corner of Massachusetts extraordinary.
As Seen In
What the World's Best Travel Writers Say
The Berkshires have earned a devoted following among the world's most discerning travel editors — from the New York Times to Condé Nast Traveler, W, Elle, and New York magazine.
W Magazine · September 2025
"The thing that amazes me about the Berkshires is the sense of community, even with people I'm meeting for the first time."
W Magazine assembled a panel of taste-making Berkshires residents — including Gourmet editor Ruth Reichl, Tory Burch's Art Director, and Eileen Fisher's head designer — for its insider guide. Their verdict: the Berkshires do chic on their own terms. Great Barrington is singled out as not to be missed; the cultural scene "heavy-hitting" and the landscape "breathtaking."
Read the full guide at W Magazine →The New York Times · 2024
"Visiting the Berkshires feels like being let in on a secret."
The Times described the region as a "rural paradise" in the midst of a "21st-century heyday," driven by farm-to-table restaurants, a mission-driven brewery scene, and the enduring pull of MASS MoCA and Tanglewood.
Read the full article at NYT →Condé Nast Traveler
"Lenox hailed as one of the 8 best weekend getaways in Massachusetts."
CNT has repeatedly recognised the Berkshires — Lenox in particular — as one of the finest weekend escapes in the Northeast, citing the region's exceptional blend of world-class arts, farm-fresh dining, and natural beauty.
Read the full guide at CN Traveler →Travel + Leisure
"Discover foliage, farm-to-table dinners, and world-class museums in the Berkshires."
T+L placed the Berkshires on multiple best-of lists including the 50 Best Places to Travel and 21 Best Places to See Fall Foliage — emphasising the rare combination of outdoor splendour with a city-calibre arts and dining scene.
Read the full feature at T+L →Elle Magazine · 2024
A Berkshires that goes far beyond leaf peeping — a destination with genuine year-round cultural depth.
Elle positioned the Berkshires as a sophisticated destination for discerning travellers — exploring the thriving restaurant scene, gallery culture, and the pleasure of driving winding back roads between villages.
Read the full review at Elle →New York Magazine · The Strategist
The complete Berkshires itinerary — from the best hikes to the restaurants you actually need a reservation for.
NY Mag's Strategist built a full Berkshires itinerary for the savvy New Yorker — specific restaurants, particular hikes, the right towns to base in, and the cultural institutions that genuinely justify their reputation.
Read the full itinerary at NY Mag →Telegram & Gazette · July 2025
Lee, Massachusetts — a hidden gem at the heart of the Berkshires.
A spotlight on Lee, MA — our home town — highlighted its exceptional position as a gateway to the best of the Southern Berkshires, with Laurel Lake, Ice Glen, and some of the region's most talked-about restaurants all within reach.
Read the full feature →Our Top Picks
Dinner Worth Dressing For
Concierge Note: The Berkshires dining scene rivals any major city. These six tables represent our absolute best — book well in advance for weekends, especially during Tanglewood season (June–September). Counter seats at Cello and the bar at Cafe Adam are always worth asking about.
Lenox · 37 Church St
Cello
Intimate, chef-driven New American with just 29 seats. The menu shifts daily around local farms and foraging — don't miss the legendary cornbread with maple butter.
Great Barrington · Jenifer House Commons
Cafe Adam
Award-winning Wine Spectator cellar, raw oysters, New England seafood, and house-smoked salmon. Chef-owner Adam Zieminski has been drawing pilgrims to Great Barrington since 2006.
Lee · Center St
The Station GastroPub
Our neighbourhood gem — elevated gastropub fare in a warm, welcoming setting right in Lee. Craft beers, artisan cocktails, and a menu that never talks down to you.
Lenox · Main St
Pizzeria Boema
Neapolitan-style wood-fired pizza with that perfect charred, chewy crust. The mortadella with stracciatella and pistachio is the stuff of Berkshires legend.
Lee · 150 Main St
Cafe Triskele
A quietly beloved local spot with a soulful, ingredient-forward menu. Intimate atmosphere and a kitchen that cares deeply about what's on the plate.
Lazy Mornings
Brunch & Morning Tables
Concierge Note: Brunch in the Berkshires is its own art form. Haven in Lenox is perfect before a Tanglewood matinee. No Comply is the Great Barrington cool-kid favourite. The Starving Artist Café has live music on weekends. Joe's Diner — inspiration for Norman Rockwell's "The Runaway" — is a local favourite for inexpensive classics.
Lee · Main St
Rose's Restaurant
The neighbourhood breakfast institution in Lee. Unpretentious, generous portions, and the kind of warmth that makes you linger over a second cup.
Lee · Housatonic St
Agave's
Mexican-inspired brunch with fresh guacamole, colourful plates, and house-made everything. Margaritas before noon? In the Berkshires, absolutely.
Lee · Center St
Starving Artist Cafe
Curated art on the walls, live music on weekends, and an excellent selection of savoury and sweet crepes. A favourite of the local arts crowd.
Lenox · 8 Franklin St
Haven Café & Bakery
Handcrafted organic ingredients, outstanding baked goods, and a menu that rewards healthy choices. The smoked salmon scramble is not to be missed. Take-away available.
Great Barrington · 258 Stockbridge Rd
No Comply Foods
The Great Barrington cool-kid favourite — exquisite combinations of flavours and textures, most dishes under $20. Inventive, plant-forward brunch that converts even devoted carnivores.
Lee · 85 Center St
Joe's Diner
The very diner that inspired Norman Rockwell's iconic 1958 painting "The Runaway." Eggs, toast, and bottomless coffee, served with a slice of Berkshires nostalgia.
"Every season in the Berkshires is the best one."
Fall foliage blazes across the hills, winter settles into cosy quiet, spring floods the valleys with green, summer fills every stage and concert lawn. This guide works year-round.
After Dark
Best Cocktail Bars
Concierge Note: Dulu is our most exciting new bar — housed in the renovated Doctor Sax House in Lenox. Station GastroPub is your local, five minutes away. Cafe Adam's bar is exceptional for a pre-dinner aperitivo.
Lenox · 35 Walker St (Doctor Sax House)
Dulu
The most exciting bar to open in the Berkshires in years. Set in the beautifully restored historic Doctor Sax House — farm-to-table cocktails, brunch, dinner, and late-night menus.
Lee · Center St
The Station GastroPub
Your neighbourhood bar, five minutes from Pleasant St. Creative seasonal drinks, excellent craft beer, and a welcome that makes you feel like a regular from night one.
Great Barrington · Jenifer House Commons
Cafe Adam — Bar & Lounge
Artisan cocktails, a 500-selection award-winning wine list, and lounge seating overlooking the wine cellar. Come early for a pre-dinner aperitivo.
Arts, Nature & Culture
Berkshires Essentials
🎭 Performing Arts
Music
Tanglewood
The summer home of the Boston Symphony Orchestra — perhaps the most beautiful outdoor music venue in America.
15 min from Pleasant St · Lenox · June–September
Dance
Jacob's Pillow
One of America's most celebrated dance festivals — ten weeks of world-class contemporary and classical dance. Many free outdoor performances.
20 min from Pleasant St · Becket · June–August
Theatre
Shakespeare & Company
World-class productions of Shakespeare and new works in an intimate theatre in the heart of Lenox.
10 min from Pleasant St · Lenox · June–October
Contemporary Arts
MASS MoCA
One of the world's largest contemporary art museums, housed in an extraordinary repurposed factory complex in North Adams.
35 min from Pleasant St · North Adams
🌿 Nature & Outdoors
Hiking
Monument Mountain
The iconic Berkshires hike — rewarded with panoramic views of the Housatonic Valley. Where Herman Melville and Nathaniel Hawthorne first met.
12 min from Pleasant St · Great Barrington
Swimming
Laurel Lake
A pristine natural lake just minutes from Lee — perfect for morning swims, kayaking, and lazy summer afternoons.
5 min from Pleasant St · Lee
Hiking
Ice Glen & Laura's Tower
A magical local trail through a glacial gorge that stays cold year-round — unique in New England. Climbs to a fire tower with sweeping views.
3 min from Pleasant St · Stockbridge Rd, Lee
Cycling
Ashuwillticook Rail Trail
An eleven-mile paved trail along a scenic reservoir and wetlands — flat, family-friendly, and extraordinarily beautiful in any season.
25 min from Pleasant St · Cheshire to Adams
🏛️ Museums & Culture
Museum
Norman Rockwell Museum
The world's most complete collection of Norman Rockwell's original works — far more emotionally powerful in person than any reproduction suggests.
12 min from Pleasant St · Stockbridge
Historic House
The Mount — Edith Wharton Estate
The extraordinary estate that Edith Wharton designed and built in 1902. Guided tours of the house and celebrated walled gardens.
15 min from Pleasant St · Lenox
Shopping & Markets
Great Barrington Village
Independent bookshops, galleries, artisan food shops, and Rubiner's Cheesemongers — a legendary destination in its own right.
15 min from Pleasant St · Great Barrington
Outdoor Sculpture
Turn Park Art Space
An extraordinary outdoor sculpture park in West Stockbridge. Large-scale works by international artists installed throughout beautifully landscaped grounds. Free to explore.
10 min from Pleasant St · West Stockbridge
Move & Sweat
Fitness & Wellness
Yoga Studio · All Levels
Yoga Lee Studio
Lee's own yoga studio — Vinyasa, Yin, candlelight yoga, barre, and Pi-Yo. Drop-in classes available. Classes fill fast on weekends — book ahead.
2 min · 62 Main St, Lee · yogaleestudio.com
Pool · Gym · Classes
Berkshire South Community Centre
25-yard lap pool, full fitness centre, Zumba, boxing, cycling classes — all included with a day pass (~$10). The Southern Berkshires' premier fitness facility.
15 min · 15 Crissey Rd, Great Barrington · berkshiresouth.org
Free Public Courts
Tennis — Lee & Stockbridge
Free public tennis courts at Lee Athletic Field (5 min) and Stockbridge Town Park (12 min). First-come, first-served. Perfect for a morning match before brunch.
5–12 min from Pleasant St · Free public access
Luxury Wellness · Day Pass
Canyon Ranch
The gold standard of American wellness resorts — 120,000 sq ft of spa, fitness, and gourmet healthy dining on 120 Berkshires acres. Day passes available; reserve in advance.
10 min · 165 Kemble St, Lenox · canyonranch.com
Yoga & Wellness Institute
Kripalu Center
One of America's most beloved yoga and wellness centres, set in a stunning former monastery above Stockbridge Bowl. Drop-in yoga and spa access available.
15 min · Stockbridge · kripalu.org
Mindfulness Resort · Day Visitor
Miraval Berkshires
Mindfulness programming, equine experiences, spa treatments, and exceptional food. Day-visitor access available on select dates.
30 min · Lenox · miravalresorts.com
Live & Local
The Music Scene
Concierge Note: Beyond Tanglewood, the Berkshires has a thriving intimate live music scene. These are the rooms where you'll find locals dancing on a Friday night — no ticket required in most cases, just show up.
Live Music Venue
The Foundry
West Stockbridge's beloved music room — folk, Americana, jazz, and rock. The kind of place that becomes your favourite the moment you walk in.
8 min from Pleasant St · West Stockbridge
Historic Inn Bar · Live Music
The Lion's Den — Red Lion Inn
The legendary basement bar of the Red Lion Inn — live music most nights in an intimate space that has been a Berkshires institution for decades. No cover, no pretension.
12 min from Pleasant St · Stockbridge
Gastropub · Live Music
Firefly Gastropub
A warm, golden-lit gastropub with a full bar and live music programme — a Berkshires speakeasy feel. Check their calendar for weekly performances.
10 min · 71 Church St, Lenox · fireflylenox.com
Café · Weekend Live Music
Starving Artist Cafe
Rotating local art and live music on weekends — singer-songwriters, folk, jazz. An intimate setting where the music feels like it was played just for your table.
2 min from Pleasant St · Lee · Weekends
This Week & Beyond
What's On in the Berkshires
Current highlights from Berkshires Week, the region's essential cultural calendar. Always confirm directly with venues.
Now On
Berkshires Farm Table Cookbook Talk
Authors Elisa Spungen Bildner and Robert Bildner in conversation about recipes, farm stories, and the agricultural life of the region.
MASS MoCA · North Adams
Details at Berkshires Week →Staged Reading
Nella Larsen's "Passing" — Live Reading
Actor Sandra Seoane-Serí brings Nella Larsen's 1929 Harlem Renaissance novel to life, with scholarly historical context.
Norman Rockwell Museum · Stockbridge
Details at Berkshires Week →Always On
Tanglewood — Summer Concert Season
The BSO's summer home. Lawn seats, wine, and the BSO under the stars. Book well in advance for weekend performances.
Tanglewood · Lenox · June–September
Tanglewood Tickets →Summer Festival
Jacob's Pillow Dance Festival
Ten weeks of world-class dance — the longest-running international dance festival in America. Many free Inside/Out performances.
Jacob's Pillow · Becket · June–August
Jacob's Pillow →Year-Round
Shakespeare & Company
Bold productions of Shakespeare alongside new plays. Outdoor summer performances on the grounds of The Mount.
Shakespeare & Co · Lenox
Productions & Tickets →Year-Round
Full Calendar at Berkshires Week
The essential guide to everything happening across the Berkshires — updated weekly with events, reviews, and recommendations.
berkshiresweek.com
Visit Berkshires Week →