Our Favourite
Places & Things
A curated guide to dining, culture, and the outdoors — written with love for this region, and updated regularly. Confirm details directly with venues as things change.
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.
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. Counter seats overlook the open kitchen.
Cafe Adam
Award-winning Wine Spectator cellar, raw oysters, New England seafood, and house-smoked salmon. Chef Adam Zieminski has been drawing pilgrims since 2006. Outdoor porch dining in season.
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.
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. Rustic barn seating out back.
Cafe Triskele
A quietly beloved local spot with a soulful, ingredient-forward menu. Intimate atmosphere and a kitchen that cares deeply. Our go-to for a relaxed evening, steps from Pleasant St.
Brunch & Morning Tables
Concierge Note: Brunch in the Berkshires is its own art form. Lee alone has three exceptional spots within a short drive. Haven in Lenox is perfect before a Tanglewood matinee. No Comply is the Great Barrington cool-kid favourite. Joe's Diner in Lee — inspiration for Norman Rockwell's iconic painting "The Runaway" — is a local institution for inexpensive classics.
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. A true local anchor.
Agave's
Mexican-inspired brunch with fresh guacamole, colourful plates, and house-made everything. A lively spot that wakes up your palate. Margaritas before noon? In the Berkshires, absolutely.
Starving Artist Cafe
Rotating art on the walls, live music on weekends, and an excellent selection of savoury and sweet crepes. A favourite of the local arts crowd — serious coffee, inventive food.
Haven Café & Bakery
Handcrafted organic ingredients and outstanding baked goods. The smoked salmon scramble and breakfast banh mi are not to be missed. Take-away available — perfect before a Tanglewood matinee.
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.
Joe's Diner
Famous as the inspiration for Norman Rockwell's iconic painting "The Runaway." Inexpensive, unpretentious, and beloved — eggs, toast, and a piece of living American history.
Cocktails & Good Company
Concierge Note: The Station GastroPub in Lee is our very own neighbourhood bar — steps from the house, warm, and reliably excellent. For something more destination-worthy, the bar at Cafe Adam has a 500-bottle wine programme and one of the most civilised atmospheres in the Southern Berkshires.
The Station GastroPub
Our neighbourhood bar — artisan cocktails, excellent craft beers, and the kind of place where you stay for one more even when you swore you wouldn't. Also excellent for dinner.
Cafe Adam — Bar & Lounge
The full Cafe Adam bar is exceptional — artisan cocktails, a 500-selection award-winning wine list, and lounge seating overlooking the wine cellar. An ideal pre-dinner aperitivo spot.
Firefly Gastropub
A warm, golden-lit gastropub with a full bar, live music programme, and a cool aesthetic that feels like a Berkshires speakeasy. A Lenox institution for nearly two decades.
The Lion's Den
The legendary basement bar of the Red Lion Inn — live music most nights in an intimate, convivial space. A Berkshires institution for decades. No cover, no pretension, total magic.
Berkshires Essentials
🎭 Performing Arts
Tanglewood
The summer home of the Boston Symphony Orchestra — perhaps the most beautiful outdoor music venue in America. From BSO weekends to intimate chamber concerts in the Shed.
15 min from Pleasant St · Lenox · June–Sep
Jacob's Pillow
One of America's most celebrated dance festivals — ten weeks of world-class contemporary and classical dance. Many free outdoor performances on the Inside/Out stage.
20 min from Pleasant St · Becket · June–Aug
Shakespeare & Company
World-class productions of Shakespeare and new works, performed in intimate settings in the heart of Lenox. Outdoor and indoor performances throughout the season.
10 min from Pleasant St · Lenox · June–Oct
MASS MoCA
One of the world's largest contemporary art museums, housed in a repurposed factory complex. Immersive installations, live performances, and rotating exhibitions that stop you mid-step.
35 min from Pleasant St · North Adams
🌿 Nature & Outdoors
Monument Mountain
The iconic Berkshires hike — a two-hour ascent rewarded with panoramic views of the Housatonic Valley. Where Herman Melville and Nathaniel Hawthorne first met. Moderately challenging.
12 min from Pleasant St · Great Barrington
Laurel Lake
A pristine natural lake minutes from Lee — perfect for morning swims, kayaking, and the kind of lazy summer afternoon that gets remembered for years. Town beach with easy access.
5 min from Pleasant St · Lee
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 of the Housatonic. A true local secret.
3 min from Pleasant St · Stockbridge Rd, Lee
Ashuwillticook Rail Trail
An eleven-mile paved trail along a scenic reservoir and wetlands — flat, family-friendly, and extraordinarily beautiful in any season. Bike rentals available in Pittsfield.
25 min from Pleasant St · Cheshire to Adams
🏛️ Museums & Culture
Norman Rockwell Museum
The world's most complete collection of Rockwell's original works — far more emotionally powerful in person than any reproduction suggests. Regularly hosts literary and cultural events.
12 min from Pleasant St · Stockbridge
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. Shakespeare & Company stages productions on the grounds in summer.
15 min from Pleasant St · Lenox
Kripalu Center
One of North America's leading centres for yoga, wellness, and mindful living — set in a breathtaking hilltop campus overlooking Stockbridge Bowl. Day programs available to non-guests.
15 min from Pleasant St · Stockbridge · kripalu.org
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. Check with each venue for schedules as they change weekly.
The Foundry
West Stockbridge's beloved music room — small, warm, loyal crowd, consistently great bookings across 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
The Lion's Den — Red Lion Inn
The legendary basement bar of the Red Lion Inn in Stockbridge — live music most nights in an intimate, convivial space. Beloved by locals and visitors. No cover, no pretension.
12 min from Pleasant St · Stockbridge · redlioninn.com
Starving Artist Cafe
Walls hung with rotating local art; weekends bring live music. 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
Firefly Gastropub
One of Lenox's most beloved rooms for nearly two decades — a warm, golden-lit gastropub with a live music programme. Feels like a Berkshires speakeasy. Check their calendar for weekly performances.
10 min from Pleasant St · 71 Church St, Lenox · fireflylenox.com
What's On in the Berkshires
Current highlights from across the region. Schedules change — always confirm directly with venues before you go.
Berkshires Farm Table Cookbook Talk
Authors Elisa Spungen Bildner and Robert Bildner in conversation — recipes, farm stories, and the agricultural life of the region.
MASS MoCA · North Adams Details at Berkshires Week →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 →Tanglewood — Summer Concert Season
The BSO's summer home — one of the great joys of the American cultural calendar. Lawn seats, wine, and the BSO under the stars.
Tanglewood · Lenox · June–September Tanglewood Tickets →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 →Shakespeare & Company
Bold productions of Shakespeare alongside new plays, by one of America's great theatre companies. Outdoor summer performances at The Mount.
Shakespeare & Co · Lenox Productions & Tickets →Revolution in America — What Does It Mean?
A PBS documentary excerpt precedes discussion with State Senator Paul Mark. Open questions about revolution and what it means to be revolutionary now.
Becket Athenaeum · Becket Details at Berkshires Week →The Berkshires in the Press
The region has earned consistent acclaim from the world's most discerning travel publications. This is why guests come — and why they return.
Condé Nast Traveler
"The Berkshires is having a serious cultural moment — and the dining scene is leading the charge."
CN Traveler placed the Berkshires on its prestigious Best Places to Go list, citing the region's rare combination of world-class arts institutions, extraordinary dining, and natural beauty — an increasingly sophisticated destination for discerning travellers.
Read the full guide at CN Traveler →Travel + Leisure
"Foliage, farm-to-table dinners, and world-class museums — the Berkshires defies easy categorisation."
Travel + Leisure has placed the Berkshires on multiple best-of lists, including the 50 Best Places to Travel and 21 Best Places to See Fall Foliage. The outdoor splendour combined with an arts and dining scene that holds its own against any major city.
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 with year-round appeal. The piece explored the restaurant scene, gallery culture, and the pleasure of driving the 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 — known for obsessively researched, no-filler recommendations — built a full Berkshires itinerary: specific restaurants, particular hikes, the right towns to base in, and 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 the village's exceptional position as gateway to the best of the Southern Berkshires. Laurel Lake, Ice Glen, and some of the region's most talked-about restaurants all within minutes.
Read the full feature →