Oak Bluffs, Martha’s Vineyard Walking Tour

Whether you are staying on the island for a week or longer, or just taking a side trip from your Cape Cod vacation, you are sure to enjoy this 90-minute stroll through the island’s most popular destination.

Ocean Park, Oak Bluffs

$20 per person

1.25-1.5 hours

Exertion level: Low

Age 8+

Departs from the Ocean Park Bandstand in Oak Bluffs, MV


Details & Itinerary

Join us on an incredible 1.5-mile walking tour of Oak Bluff’s most scenic neighborhoods and attractions. Along the way, we will learn about the island’s history, it’s transition from a religious summer camp to a bustling vacation destination, and enjoy some of the best scenery in town. Food and beverages are not included, but there will be opportunities to stop along the way for some of the islands signature treats.

  • Times are variable. Please check the calendar HERE for availability.
  • Meet at the bandstand (gazebo) in Ocean Park, near the Steamship Authority ferry terminal.
  • Allow 90 minutes to complete the tour, which ends at Oak Bluffs Harbor, just a block away from the starting location.
What You Should Bring
  • We will be doing a fair amount of walking. Wear sneakers or otherwise comfortable shoes. You should be able to get away with an active sandal such as Keen, Merrell, or Teva brands.
  • You might want to bring along a bottle of water. We can stop along the way if needed.
  • Camera. Photos will be taken during the tour and are complimentary.
Best Times for This Excursion
  • May through October is a great time to visit Boston.
  • The tour operates on any fair-weather day.
How strenuous is this?
  • Martha’s Vineyard is a relatively flat area, and those in moderately good shape should be able to complete the tour.
  • You should be able to walk 1.5 miles without difficulty in order to enjoy this tour. We will be stopping at many points along the way, so it is not a continuous walk.
  • Please be mindful of the weather. Excessive heat in the summer months will make the tour uncomfortable for some.

Guided By Experts

Your guide (that’s me, Gregg), knows the area well and has spent countless hours walking the island for business and pleasure.

A Great Way to Take in Some of the Island’s History 

We will explore all of the most notable sights in town, including the famous gingerbread cottages, beaches, commercial district, and Oak Bluffs Harbor. We will talk about how each of these areas has contributed to the island’s identity and culture, unlike anywhere else in America. 

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