Discovering Oak Bluffs: A Tour Through Martha’s Vineyard’s Historical Retreat

(22 reviews)

Martha's Vineyard, Massachusetts audio tour: Discovering Oak Bluffs: A Tour Through Martha’s Vineyard’s Historical Retreat

This is a 1.5mi walking tour

It takes an average of 75 mins to complete.

Martha's Vineyard, Massachusetts

The United States

$11.99

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About the Tour

Discover how a small religious summer camp transformed into one of Martha’s Vineyard’s most popular island destinations on this walking tour through the town of Oak Bluffs.

Starting in Ocean Park, you’ll follow the coast to Inkwell Beach before heading into the heart of the town. Along the way, you’ll hear its history and find out what makes this island paradise so alluring to everyone from the rich and famous, to curious Cape Cod vacationers that come for a day. Around Trinity Park, you’ll see Martha’s Vineyard Camp Meeting Association, its cottage museum, and the Tabernacle in Oak Bluffs which is a place of worship. After heading down Circuit Avenue, where I’ll show you the town’s famous Flying Horses Carousel, our tour will come to an end at the harbor.

By the end of this tour, you’ll have the answers to questions like:

How did Martha’s Vineyard get its name?
What is the origin of the famous gingerbread cottages?
Who are some of Oak Bluffs’ most notable African-American cultural icons?
How did Oak Bluffs go from a religious settlement to a secular resort town?
What is the most famous (and delicious) drink on the island, and where do you get it?

Whether you’re on the island for only a day, or calling Martha’s Vineyard home for the season, this tour is for anyone who wants to dig into Oak Bluffs’ past and enjoy its present. Allow 60-90 minutes to get the most out of this tour. There are a few places to stop along the way in case you’d like some relief from the sun, or to grab a drink or bite to eat.

Tour Producer

Gregg Squeglia

4 tours

I am a travel writer and tour guide based in Massachusetts. I love to write and share what I have learned with others. During the summer, I provide guided bike tours here on the beaches of Cape Cod and walking tours of Martha's Vineyard.

I grew up in Lowell, Massachusetts - a historic city in its own right about 30 minutes from Boston. In elementary through high school classes, I learned about America's beginnings and all of the historic events that happened practically right around the corner. The colonial period quickly became one of my favorite eras in the nation's history.

I am also an officer in the US Army Reserve. This has taken me to many places across the country and even the world. During my travels, I try to learn as much as I can about the area, its history, and the people who call it home. Many of my travels are documented on my website, Knockabout Travel.

Preview Location

Location 1

Ocean Park Bandstand (Gazebo)

Hello, and welcome to Martha’s Vineyard. My name is Gregg, and I’ll be your guide today as we take a walk through beautiful and historic Oak Bluffs. As we walk, I’ll be pointing out some of the finer details of the sights along the way including the history of the town, the be... Hello, and welcome to Martha’s Vineyard. My name is Gregg, and I’ll be your guide today as we take a walk through beautiful and historic Oak Bluffs. As we walk, I’ll be pointing out some of the finer details of the sights along the way including the history of the town, the best places to stop and grab a meal or some memorabilia to take home, and how to make the most of your time here in town.

As we begin here in front of the bandstand in Ocean Park, take a minute to visualize how this landscape looked over 130 years ago. You may have the impression that large summer crowds on Martha’s Vineyard are a recent phenomenon, but in fact, people have been vacationing in some form here since the 1830s, and by the 1870s, there were several grand hotels here in Oak Bluffs to accommodate the massive amounts of visitors, along with a railroad to transport people and goods from here to Edgartown.

Ocean Park is a seven-acre green space overlooking Nantucket Sound that makes an incredible first impression for passengers just disembarking the ferry from the mainland. One of the great things about Oak Bluffs is that it was designed as a residential and tourist community from its inception by the Oak Bluffs Land and Wharf Company and included plenty of parks and green spaces, Ocean Park being the largest amongst them. Erastus Carpenter, the lead visionary of the Land and Wharf Company, wanted visitors arriving by ferry to have a memorable first impression of the town, and so this grand park was deliberately placed here for that very reason. The walking paths that cut through the park were initially designed as automobile roads but were quickly repurposed as pedestrian routes to allow a safer play area for children.

In the center of the park is the bandstand, constructed in 1867 in preparation for a visit from President Ulysses S. Grant. The structure was intended to host live music during the President's visit and it continues that purpose today. During summer evenings, visitors and residents gather regularly to hear the town band perform.

Let's get walking. From here, with the bandstand behind you and the ocean on your left, you should see a forked walking path ahead. Stay right at the fork and walk to the edge of the park.

While you walk, let me briefly explain how VoiceMap works.

It uses your location to play audio automatically, at the right time and place. Don't worry if I'm silent at times, when I'm not giving directions or telling stories. There's a map on your screen if you ever feel lost, and if you do get way off track without noticing, VoiceMap will let you know. Read More

View locations and route

How VoiceMap Works

Focus on your surroundings, not the screen

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Major Landmarks

Ocean Park
Corbin Norton House
The Overton House
Inkwell Beach
Martha's Vineyard Camp Meeting Association
Martha's Vineyard Camp Meeting Association Cottage Museum
Trinity Park
Tabernacle in Oak Bluffs
Circuit Avenue
Flying Horses Carousel
Oak Bluffs Harbor

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Getting There

Route Overview

VoiceMap tours follow a route from a set starting point. It’s how we give turn-by-turn directions and tell a story greater than the sum of its parts.

Start location
2 Seaview Ave, Oak Bluffs, MA 02557, USA
Total distance

2km
Final location
Oak Bluffs Harbor, Oak Bluffs, MA, USA
Distance back to start location

364.18m

Directions to Starting Point

The tour begins at the bandstand in Ocean Park, located across from the Steamship Authority ferry terminal. If you are arriving in Oak Bluffs via the Steamship Authority ferry, then you will see the bandstand when you disembark the boat. If you are arriving via the Island Queen ferry, then simply walk up Seaview Ave. with the ocean on your left until you reach Ocean Park (~6 minutes).

If you arrive on the Steamship Authority into Vineyard Haven, then take the #13 bus to Oak Bluffs. The bus stop is located to the right as you disembark the ferry. This bus will take you directly to Ocean Park. You can also take a taxi or ride-share.

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Tips

Places to stop along the way

• If you want a quick bite, then Giordano's near Ocean Park has very good pizza by the slice as well as fried/broiled seafood options. Use the takeout window and picnic on the lawn at Ocean Park.

• Offshore Ale is a brewpub with a large menu of pub food and beers brewed on-site.

• The largest selection of beers on tap can be found at Coop deVille on Oak Bluffs Harbor. The tour will guide you past this location.

• Donovan's Reef is the outdoor bar at Nancy's on Oak Bluffs Harbor. Be sure to get a Dirty Banana before leaving. This is the ending point on the tour.

Best time of day

Anytime from dawn to dusk.

Precautions

Please use crosswalks for all street crossings. If using headphones, it is recommended to listen with only one earphone while walking in areas with automobile traffic so that you can be best aware of your surroundings.

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App Store Review

“Great app. walk around at your own pace, stop where you want, move on or speed up when you want. Read the script before you go or during the commentary, speed it up or replay it. Repeat the tour whenever you like.”