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Things To Do

Welcome to Osterville!

“Baby Beach” (Wianno Avenue)

Wianno Avenue, Osterville, MA 02655

At the very end of Wianno Avenue sits a small sandy shoreline fondly known to locals as “Baby Beach.” This neighborhood spot is quiet, shallow, and easy to manage with little ones, making it especially popular with young families. While not as large or developed as other beaches, it offers a charming, tucked-away place to dip your toes in the water and take in the harbor views.

Craigville Beach

966 Craigville Beach Road, Barnstable, MA 02632

One of the more popular beaches on Cape Cod, Craigville Beach features a massive parking lot, full facilities and activities to keep everyone in the family entertained for the day. The warm, calm waters are great for swimming and the soft sand is perfect for long walks along the shore. There are a few restaurants across the street for an easy bite to eat.

Main Street

Main Street, Osterville, MA

Osterville proper is wonderfully walkable. Main Street, the heart of the village, is lined with locally owned shops, a hardware store, delectable bakery, and hometown eateries like Wimpy’s Seafood Café. You can stroll from the library to Armstrong-Kelley Park, past the post office, and down to the marina without ever needing your car.

Mashpee Commons

22 Steeple Street, Mashpee, MA 02649

Mashpee Commons is a shopping and living community comprised of over 100 businesses and 77 residential units. Our neighborhood features unique dining and cafés, local shops and boutiques, fresh markets, fitness studios, beauty services, national favorites and entertainment for the whole family. The Commons is conveniently located at the rotary that connects routes 28 and 151 and has become a renowned shopping destination at the heart of Mashpee, MA.

Chart Room Osterville

330 West Bay Road, Osterville, MA 02655

The Chart Room Osterville is a family owned and operated restaurant established in 2017. Perfectly crafted cocktails, delicious seafood, ocean views with a warm and fun atmosphere make The Chart Room a Cape Cod classic.

Five Bays Bistro

825 Main Street, Osterville, MA 02655

Located in the heart of one of the most picturesque villages on Cape Cod, Five Bays Bistro offers modern yet classic food and atmosphere worthy of a major city. The Bistro serves award winning contemporary new American cuisine, with a more casual small plates menu at the bar.

Crisp

791 Main Street, Osterville, MA 02655

CRISP Flatbread serves fresh wood-fired pizza and homemade pastas prepared with seasonal, local ingredients. They support local farmers, and are passionate about using hormone and nitrate-free meats and organic vegetables whenever possible. All of their pastas, sauces and CRISP flatbread dough are made from scratch with love. Relax on the outdoor patio, cook a s'more at the fire pit, and challenge friends (old and new) to a game of table tennis. CRISP. there's nothing else like it on Cape Cod!

Amie Bakery

1254 Main Street, Osterville, MA 02655

They're a scratch bakery with a Parisian vibe on beautiful Cape Cod, open for breakfast, lunch, coffee, pastry, cakes, cocktails, and classes. Located in Osterville, they are committed to scratch baking using whole, high quality ingredients. They don't use any box mixes or premade fillings. Once you try the real thing, you can't go back.

Pain d'Avignon Osterville

10 Wianno Ave, Osterville, MA 02655

A lovely French-inspired bakery and café located in the charming village of Osterville. Pain d’Avignon is known for its freshly baked artisan breads, buttery croissants, delicious pastries, and European-style café favorites. Whether you're stopping in for a morning coffee and breakfast, picking up a sweet treat, or enjoying a casual lunch, it’s a wonderful spot to relax and soak in the charm of downtown Osterville.