Best Restaurants in Osterville, MA

Waterfront Seafood & Bar

A beloved Osterville waterfront institution on West Bay, the Chart Room is the go-to spot for fresh seafood, cold drinks, and stunning harbor views. The deck is one of the best places on Cape Cod to watch the boats come in while enjoying a lobster roll or raw bar platter.

Casual Seafood

A beloved Osterville landmark since 1938, Wimpy's is the quintessential Cape Cod seafood shack. Famous for its fried clams, fish & chips, and lobster rolls, it's the kind of place that defines summer on the Cape. Casual, friendly, and consistently excellent.

Upscale Casual

A beloved Osterville dining staple, Five Bays Bistro delivers creative American bistro fare in a warm, welcoming atmosphere. Known for its inventive seasonal menu, excellent wine list, and consistently outstanding service — a true village gem.

Fresh & Fast Casual

A popular Osterville spot serving fresh, made-to-order salads, wraps, and bowls. CRISP is the go-to for a light, healthy meal using quality local ingredients — perfect for a quick lunch or a casual dinner after a day on the water.

Artisan Chocolate & Sweets

Osterville's beloved artisan chocolate shop, Gone Chocolate crafts exquisite handmade chocolates, truffles, and confections using premium ingredients. A must-stop for anyone with a sweet tooth — and the perfect place to pick up a gift that captures the spirit of Cape Cod.

Artisan Bakery & Café

A beloved Osterville bakery and café serving beautifully crafted pastries, breads, and light fare. AMIE Bakery is the perfect morning stop for a flaky croissant, fresh coffee, and a taste of village life on Cape Cod.