THE BERKSHIRES
New Marlborough summer pink sky sunset over the Whiting River valley — no filter.
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 and the vibes at his bar next door.
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 & drink
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 to thirty minutes southwest
New York
Forty minutes west
Zinnia's Dinette → fish fry & tinned fish
The one place we'd send you this far for. A New England fish fry on a long stretch of country road in Craryville, headed toward Hudson. Amy Lawton grew up in Rhode Island and the menu shows it — fish and chips, steamed mussels, a cup of clam strips, crunchy fries with house slaw and dill sauce, plus outstanding fried chicken and a couple of salads so there's something for everyone. One wall is tinned fish, hundreds of varieties from around the world, and Lawton is often behind the counter opening one for someone to try.