Best road-trip restaurants in Massachusetts

$$$ · Boston Marathon

Subterranean Harvard Square hit for inventive shared plates.

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Named Boston Magazine's Best New Restaurant of 2026, occupying the former Craigie on Main space in Central Square.

$$$ · Pennsylvania Dutch & Berkshires

Farmer-restaurateur's rustic spot serving elevated American cuisine and herb-garnished cocktails built around ingredients from its own farm.

$$$ · Mohawk Trail

A Greenfield dinner upgrade for the Mohawk Trail corridor when the day deserves a slower meal than a roadside snack.

$$$ · Pennsylvania Dutch & Berkshires

Chef-driven 28-seat dining room in the former Nudel space, built on local ingredients and a seasonally inspired farm-to-fork menu.

$$$ · Mohawk Trail

A Shelburne Falls dinner pick that gives the Mohawk Trail a polished stop near the Bridge of Flowers.

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Refined Union Square New American with a seasonal menu and lauded wine and cocktail program in an understated space.

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Andrew Brady and Sara Markey's farm-driven Union Square restaurant built on hyper-seasonal produce and a natural wine list.

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Ambitious Union Square spot pairing counter-service breakfast with prix-fixe dinners rooted in French and New American technique.

$$$ · Pennsylvania Dutch & Berkshires

Tiny intimate bistro tucked in the Mews serving seasonal New American plates, a longtime Stockbridge fine-dining favorite.

$$$ · Mohawk Trail

A Connecticut River valley dinner stop that gives the Mohawk Trail corridor a more polished option near the eastern approach.