Discover Oak Bluffs

Oak Bluffs offers a variety of options for planning your trip, from culture and history to beaches, bike trails and activities at the harbor. If you’re looking for a hotel in Oak Bluffs, first consider which of these interests you want your trip to focus on.

Culture and History

At the Cottage Museum, visitors can tour the interior of a typical Campground house, furnished in period style. The focus is therefore on a furnished interior. The Flying Horses Carousel has delighted visitors in Oak Bluffs since 1884 and is the oldest platform carousel in the country. These two cultural experiences offer different highlights: the museum focuses on the inside of the house, while the carousel stands out for its long history and status as the country’s oldest platform carousel.

Tours and Summer Gatherings

A fully narrated tour is offered in the Highlands area of Oak Bluffs, covering six stops on the African-American Heritage Trail. Seasonal availability may change, so check current tour information before making plans.

For nearly 80 years, the Polar Bears Club has brought people together for summer gatherings at Inkwell Beach. This offers a different focus from the tour: these gatherings center on spending time together at the beach, while the tour provides commentary at six stops along the Heritage Trail. The gatherings take place in summer; tour availability may change seasonally.

Beach, Walks and Island Access

Oak Bluffs Town Beach offers gentle waters and a sandy beach. Ocean Park is home to a historic pavilion. If you’re weighing up beach and park options, their highlights differ: Town Beach is all about the water and sand, while Ocean Park is known for its historic pavilion.

A walk to East Chop Lighthouse offers a photo opportunity. If you’d like to combine a walk with a specific photo subject, this is one point to consider in your plans. Oak Bluffs Marina provides access to the rest of the island. This is relevant if you also want to include the rest of the island in your trip.

Cycling and Harbor Activities

The Down-Island bike trails include a route from Vineyard Haven through Oak Bluffs to Edgartown. The route is mostly flat and easier for both children and adults to manage. Its course and terrain can help you assess it as a cycling option, taking into account both the places it passes through and the type of route.

Fishing trips aboard charter boats are offered at Oak Bluffs Harbor, and watersports are also available there. These are two different types of water-based activities to consider when planning: a fishing trip by charter boat or watersports at the harbor.

Discover more destinations: Tisbury, Aquinnah, West Tisbury, Edgartown.

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