The Travelers’ Field Guide toMassachusetts
Discover Massachusetts’s Hidden Gems and Unique Attractions
Massachusetts is layered with history, but it’s also full of surprises. Wander cobblestone streets in seaside towns, hike wooded trails in the Berkshires, catch a ferry to the islands, or stumble upon quirky roadside stops that feel worlds away from Boston. From Revolutionary landmarks and world-class museums to quiet beaches and small-town diners, the Bay State mixes the classic with the unexpected at every turn.
UPDATED SEPTEMBER 2025
Places to Eat and Drink In Massachusetts
Massachusetts serves up a mix of tradition and innovation on the table. From clam shacks and lobster rolls by the shore to cozy taverns, farm-to-table cafés, and inventive city restaurants, food here feels both familiar and fresh. Add in cranberry bogs, cider mills, craft breweries, and wineries tucked into rolling hills, and you’ll find plenty of flavors worth the trip. Whether you’re grabbing a snack after a hike or planning a night out in Boston, the Bay State has you covered. Want more? Start with MassGrown for farm-fresh finds, follow the Massachusetts Wine & Cheese Trail, or check Visit Massachusetts for food and drink guides.
Family-Friendly Favorites
Casual spots that make dining easy for everyone—pizzerias with big tables, diners serving breakfast all day, and seafood joints with menus kids and adults can both enjoy.
Roadside Classics
Fried clam shacks, neon-lit diners, and cider stands that feel straight out of New England nostalgia. Simple, satisfying, and always worth the stop.
Date-Worthy & Romantic
Share a meal by candlelight in Boston, enjoy a harbor sunset on the Cape, or linger over wine and seasonal dishes in a historic inn.
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Red Lion Inn – Stockbridge, MA
A historic Berkshire inn where generations have gathered, rested, and celebrated. From its wide front porch to its many tucked-away rooms, it remains a place where time feels layered, not preserved.
Wineries & Breweries
Breweries, cideries, and vineyards are scattered across the state, many with patios, tasting flights, and weekend music. A perfect excuse to slow down.
Sweet Spots
Ice cream counters, small-town bakeries, and donut shops—plus regional icons like Boston cream pie and cranberry sweets.