Osterville, Massachusetts

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Osterville is a village in the town of Barnstable, Massachusetts. Located on the south side of Barnstable, Osterville is primarily residential and includes inlets and harbors for fishing and boating and a small business district.

Osterville from the air
Osterville from the air

In the summer, Osterville thrives due to a predominantly seasonal make-up of its residents. Many maintain a second house in the area while spending most of their time in Greater Boston.

Notable residents include:

Armstrong-Kelley Park, the oldest and largest privately-owned park on Cape Cod, is located in Osterville. Crosby Boat Yard is the home of the famous Crosby catboat, and the Wianno senior[1], both renowed in the sailing field and the latter a favorite of nearby Hyannisport resident President John F. Kennedy.

A drawbridge connects the town to Little Island and Great Island (also known as Oyster Harbors), a gated community featuring many luxury homes and a country club. The neighborhood of Wianno abuts the East Bay section of Osterville, and is home to the Wianno Inn, a longtime inn and function hall. One of the legends about the Inn tells of Robert F. Kennedy riding a donkey up the front stairs of the hotel entrance during a wedding reception.

The town is also home to Earthly Delights, Wimpy's Restaurant, Gone Chocolate and Ice Cream, Sweet Tomatoes, The Foxhole, and Joe's Twin Villa establishments, popular with many young summer residents.

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Coordinates: 41°37′42″N, 70°23′13″W