Oak Bluffs Walking Tours

Fall Oak Bluffs Walking Tours Schedule

Wednesdays – 10:00am

Please call if you would like to schedule a private tour at another time.

campground gingerbread cottagesOverview of Oak Bluffs Walking Tours

The best way to really see Oak Bluffs is by foot! Join us for an informative and entertaining walk around this quaint and colorful town. Highlights of the tour include the development of the Methodist Camp Meeting Association from tents to the storybook “Gingerbread Cottages”, the development of Cottage City and its many parks by the Oak Bluffs Land and Wharf Co., the Overton House – known as the Summer Whitehouse of the Civil Rights Movement, Union Chapel, Ocean Park, Dreamland and the Flying Horses Carousel. The tour also includes an overview of Martha’s Vineyard and its current demographics.

Pricing:  Adults – $15.00
Children – $8.00  (ages 6 – 12)
Under 6 – free

Tour is approximately 75 minutes and includes about 1.5 miles at a leisurely pace. Route includes Circuit Avenue, Tuckanuck Ave, Seaview and Lake Avenues, and the Oak Bluffs Harbor area. Sites of historic significance will be viewed, such as Union Chapel, the Villa Rosa, Dreamland and the Flying Horses. You will also view some of the whimsical Gingerbread Cottages and the grand Victorian mansions along Ocean Park and Nantucket Sound.

Things To Bring

Please wear comfortable walking shoes and dress appropriately for the weather.


Guide gratuity is not included in price.

Cancellation Policy

Our tour sizes are limited so that we can offer the optimum, personalized experience of a small group. Making advance reservations will guarantee your space but may mean that others are turned away.  Our tours go out rain or shine. In the unusual circumstance of severe weather, we reserve the right to cancel the tour.


Tours start at the intersection of Lake & Oak Bluffs Avenues, by the Tourist Information Booth and will end in front of the Oak Bluffs Harbor on Lake Avenue.

Tour Reservations

Please call us at 508-499-TOUR (8687) with questions and to reserve your spot!

Owen Park, Oak Bluffs Martha's Vineyard MA