A working vineyard hiding in plain sight in East Falmouth, Cape Cod Winery produces estate wines with real local character — from crisp whites to a beloved Cranberry Wine. A must-visit for foodies and couples looking to uncork something special on the Cape.

Tree House Brewing's legendary hazy IPAs have arrived on the Upper Cape, and the Sandwich taproom lives up to every bit of the hype. Grab a Julius, load up on four-packs, and settle in — this is a craft beer pilgrimage worth making.

Named after a Wampanoag word for wandering, Naukabout Beer Company is Mashpee's laid-back craft brewery pouring standout IPAs and seasonals in a taproom that feels like the Cape at its most relaxed. Live music, outdoor seating, and rotating taps make it a must-stop.

A genuine Italian-American trattoria hiding in the gorgeous, undervisited village of Cotuit — housemade pasta, slow-cooked sauces, and the kind of warmth that makes you feel like a regular on your first visit.

Trevi brings warm, polished Italian-American cooking to Mashpee Commons, with handmade pastas, classic entrées, and a wine list that makes date night easy. One of the Upper Cape's most reliable spots for a proper sit-down dinner.

Sandwich Taverna brings genuine neighborhood warmth to Cape Cod's oldest town — craft beers, comfort food done right, and a vibe that makes locals and visitors feel equally at home.

Asti Mashpee brings genuine Italian-American warmth to Mashpee Commons, with house-made pastas, a thoughtful wine list, and a room that earns its date-night reputation. A mid-Cape staple that punches well above its strip-shopping-center surroundings.

Lo Scafo brings genuine Italian warmth to Cape Cod's oldest town, with house-made pastas, locally sourced seafood, and a romantic dining room that makes any night feel like a special occasion. Sandwich's best-kept secret for a proper sit-down Italian meal.

A legendary waterfront institution at Cataumet's Kingman Marine, the Chart Room serves classic New England seafood and cold drinks from a deck perched right over the marina. Arrive by car or tie up your boat — either way, the lobster bisque is non-negotiable.

Right off the Sagamore Bridge, The Lobster Trap delivers everything Cape Cod seafood promises — buttery lobster rolls, thick chowder, and whole lobsters fresh from the tank. A classic, no-frills gem that earns its reputation with every bite.