THE BERKSHIRES
Closest
Walk down the mountain
Southfield Store → cafe & community spot
Open early for coffee, lunch til 4, brunch Sundays, dinner Wednesday through Saturday. Best espresso in South County, pulled on a La Marzocco Strada. Chef Gustavo Perez running a locally sourced kitchen — eat in, takeout, or family style.
Old Inn on the Green → dinner & taproom
Sister to the Southfield Store. Owner and Executive Chef Peter Platt runs a candle-lit dining room and a small taproom in an inn that's served the area for 260 years. Ask for Jesse at the bar.
Gedney Kitchen → grill & wine
Wood-fired Argentinian grill and field-stone oven, locally sourced and seasonal. A somm-curated list of small-production wines from around the world. Walk it off through their gardens and out into the meadows.
A short drive
Six minutes by car
Great Barrington
Twenty minutes north
Cafe Adam → dinner
Our favorite. Nearly all ingredients sourced locally — from bakers, mongers, butchers, growers, fromagers. Equally great at the bar or a table, and they can take a big group without compromising the menu.
GB Eats → breakfast / lunch
Casual spot on Main Street. Order a side of waffles with nearly anything. Adults, kids, you won't leave hungry.
Roberto's → pizza
His flagship in Sheffield. Roberto's a first-generation Mexican-American who hustled hard and put his heart into the place. One bite and you'll see why we love his pies.
Aroma Bar & Grill → Indian takeout
The Chahal family. An impressive variety of authentic, spiced-to-order regional plates. We think it's best in the Berkshires.
Lucy's Rendezvous → darts & a crew
Down an alley, door not well-marked — part of the field trip. Room for the whole party, plus darts.
Modern Milk Bar → ice cream
Family-owned. 20+ homemade flavors made right there. Grab pints to bring back, or tell us in advance and we'll have them waiting in your freezer.
The Woodland → dinner
Fantastic bar for a cocktail and dinner. Expansive menu, sushi to steak au poivre — if a dish is on it, it's because it's excellent. The sushi is the best in a 50-mile radius.
The White Hart → cozy bar
Wood-burning fireplace, quiet tables in corners, six-seat tap room bar — a properly romantic spot with upscale comfort food.
Deano's Pizza → old school slice
Old school slice if you're driving by. Their "About Deano" page on the site is worth the click.
Grassland Dessert Cafe → ice cream
Old-school parlor vibes in a freshly renovated house. Great coffee drinks too.
Connecticut
Twenty minutes southwest
New York
[wayfinding TBD]
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