Things To Do in Osterville, MA

Wianno Yacht Club

One of the most prestigious yacht clubs on Cape Cod. Home to the famous Wianno Senior class sailboat and a hub of Osterville sailing culture.

East Bay Sailing

Explore the beautiful waters of East Bay and Nantucket Sound by sailboat. Rentals and lessons available seasonally.

Deep-Water Docking

Oyster Harbors and East Bay offer some of the finest deep-water docking on Cape Cod for larger vessels.

Wianno Club Golf

A private 18-hole course considered one of the finest on Cape Cod. Members and guests enjoy stunning views and impeccably maintained fairways.

Osterville Golf

Several public and semi-private courses are within easy reach of Osterville, including options in Hyannis and Centerville.

Cape Cod Golf Trail

Cape Cod is home to 40+ golf courses. Osterville's central location makes it an ideal base for exploring the region's best courses.

Main Street Boutiques

Osterville's Main Street is lined with upscale boutiques, antique shops, and art galleries. A world away from the typical Cape Cod tourist strip.

Osterville Art Galleries

Several fine art galleries showcase local and regional artists. The Osterville art scene is intimate and sophisticated.

Antique Shops

Osterville is known for its exceptional antique dealers, offering everything from Cape Cod maritime art to fine New England furniture.

Kayaking & Paddleboarding

Explore the calm waters of East Bay, West Bay, and the kettle ponds by kayak or paddleboard. Rentals available seasonally.

Swimming at Dowses Beach

Dowses Beach offers calm, warm Nantucket Sound waters ideal for swimming and water play.

Fishing

Excellent fishing in the bays, ponds, and offshore waters. Charter boats available from nearby Hyannis Harbor.

Osterville Historical Museum

Explore the rich history of Osterville and Cape Cod through exhibits, artifacts, and historic buildings.

Cape Cod Melody Tent

Just minutes away in Hyannis, the iconic Melody Tent hosts national touring acts and concerts all summer.

Village Events

Osterville hosts a series of charming village events throughout the year, from art walks to holiday celebrations.

Kettle Pond Walks

Osterville is surrounded by beautiful kettle ponds formed by glaciers. Walking trails offer scenic nature experiences.

Birdwatching

The marshes, ponds, and shoreline around Osterville are exceptional for birdwatching, especially during migration seasons.

Cape Cod Rail Trail

The paved multi-use trail passes through the Barnstable area, offering cycling and walking through beautiful Cape Cod scenery.