Oak Bluffs Martha’s Vineyard Audio Tour
Self-Guided Walking Tour through history, architecture, and island life
What to Expect
Discover the heart of Martha’s Vineyard on a self-guided audio walk through Oak Bluffs, where colorful cottages, oceanfront parks, and deep cultural roots come together by the sea. From the whimsical homes of Wesleyan Grove to Ocean Park’s sweeping lawns and the historic shores of Inkwell Beach, each stop reveals a story of faith, leisure, and community. Follow GPS-activated narration past landmarks like the Flying Horses Carousel, Union Chapel, and the Mariposa Museum as history unfolds around you. Blending architecture, storytelling, and ocean breeze, this tour captures the spirit of Oak Bluffs in every step.
Ready to go? Book below or download our app and purchase directly from your phone.
📍 Location: Martha’s Vineyard, MA
🚶♂️ Type: Walking tour
⏱ Duration: Approx. 90 minutes (flexible)
✅ Includes: App download, GPS-triggered audio, No expiration
📶 Works Offline: Download ahead of time - no cell service required
🎧 Multiple Languages: English, Spanish
Get Ready for Your Oak Bluffs Self-Guided Tour
Explore the vibrant seaside town of Oak Bluffs at your own pace with this self-guided walking tour.
Wander among its storybook cottages, breezy harbor views, and tree-lined avenues, each revealing tales of creativity, community, and faith that shaped this one-of-a-kind Martha’s Vineyard destination.
Once a 19th-century Methodist retreat, Oak Bluffs evolved into one of America’s earliest seaside resorts—celebrated for its whimsical Victorian architecture and inclusive spirit.
Along the way, you’ll discover how it became a cherished haven of African American culture and summer tradition.
Combining history, charm, and coastal scenery, this tour brings Oak Bluffs to life—where every cottage, chapel, and shoreline pathway reflects the island’s enduring sense of joy and belonging.
What You’ll See on Your Oak Bluffs Walking Tour
Cottage Museum & Gift Shop
Step into this charming museum for a glimpse of 19th-century life inside one of Oak Bluffs’ iconic gingerbread cottages. Period furnishings and delicate details evoke the island’s early summer days, while the gift shop showcases local artistry and island keepsakes.
Circuit Avenue
Buzzing with energy and color, Circuit Avenue is Oak Bluffs’ lively main street, filled with cafés, boutiques, and classic summer treats. Wander its length to experience the joyful pulse of Vineyard life in full swing.
East Chop Lighthouse
Standing tall on the bluffs above Vineyard Haven Harbor, East Chop Lighthouse has watched over sailors for generations. Its graceful white tower and sweeping coastal views make it one of the island’s most beloved landmarks.
Flying Horses Carousel
Dating back to 1876, this hand-crafted carousel is the oldest continuously operating one in the United States. Hop aboard for a whirl of nostalgia and try your luck at catching the brass ring—an Oak Bluffs tradition for over a century.
Giordano’s Famous Fried Clams
Since 1930, Giordano’s has been serving up crispy fried clams and hearty Italian classics just steps from the shore. A visit here is a bite of Vineyard history—and a must for seafood lovers.
Inkwell Beach
A cherished gathering spot, Inkwell Beach is both a place of relaxation and a symbol of cultural pride. Its calm waves and storied history reflect the strength and spirit of the island’s African American community.
Oak Bluffs Harbor
This bustling marina is the heart of Oak Bluffs’ waterfront life, where fishing boats and yachts share the docks. Come for the sea breeze by day or the lively dining and music that fill the air after sunset.
Ocean Park
Framed by graceful Victorian homes and open to Nantucket Sound, Ocean Park is Oak Bluffs’ most iconic green. Whether flying a kite, enjoying a picnic, or watching fireworks, it’s a postcard-perfect slice of island life.
Wesleyan Grove’s Gingerbread Cottages
Lose yourself among the storybook cottages that once housed 19th-century Methodist campers. With lacy trim, vivid paint, and cozy porches, this neighborhood feels like stepping into a fairytale village by the sea.
The Tabernacle
Built in 1879, the Tabernacle anchors Wesleyan Grove as a center of community life and celebration. The open-air pavilion hosts concerts, gatherings, and the famed Illumination Night, when lanterns transform the evening into magic.
Union Chapel
Since 1870, Union Chapel’s distinctive octagonal design has welcomed people of all faiths to gather in reflection and song. Its simple elegance and inclusive history embody the welcoming spirit of Oak Bluffs.
Waban Park
Between Ocean Park and the water’s edge, Waban Park offers wide lawns perfect for flying kites or lounging under summer skies. It’s where festivals, family picnics, and ocean breezes come together in true Vineyard style.
Mariposa Museum
This museum brings stories of the African diaspora to life through art, culture, and conversation. Thought-provoking and uplifting, it invites visitors to explore the diverse narratives that continue to shape American identity.
Joseph Sylvia State Beach
Running between Oak Bluffs and Edgartown, this long stretch of sand is known for calm waters on one side and ocean surf on the other. It’s also home to the famous “Jaws Bridge,” a favorite stop for movie fans and brave jumpers alike.
Strand Theatre
Once the go-to spot for island movie nights, the Strand Theatre remains a beloved reminder of Oak Bluffs’ golden summers. Its vintage façade hints at the town’s enduring love of music, film, and community gathering.
Oak Bluffs Town Beach
Just steps from the harbor, this inviting stretch of sand offers gentle surf and scenic views of moored boats. Perfect for families, it’s an easygoing spot to swim, relax, or watch the ferries drift by.
The Corbin Norton House
A masterpiece of Gothic Revival design, this ornate cottage—with its delicate trim and towers—was painstakingly restored after a devastating fire. Today, it stands as a proud symbol of Oak Bluffs’ creativity and resilience.
The Overton House / Villa Rosa
Built by Harlem businessman S. J. Overton in the 1920s, Villa Rosa became a summer retreat for influential Black artists and thinkers. Its legacy as a cultural landmark continues to shine through Oak Bluffs’ vibrant community.
Meeting Point
Your Oak Bluffs walking tour begins at The Attleboro House.
The tour begins at the corner of Lake Avenue and Hebron Avenue, on the shore at Oak Bluffs Harbor. The starting point is very close to Nancy's Restaurant.
FAQs About Our Oak Bluffs Walking Tour
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Tickets to the East Chop Lighthouse are sold by the Martha’s Vineyard Museum Museum and cost the following:
Adults: $5
Children 12 & Under: Free
MV Museum Members: Free
Visit the Martha’s Vineyard Musuem website for more information.
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Tickets to the Flying Horses Carousel cost the following:
1 Ride: $3.50
10 Ride Pass: $30
Visit the Vineyard Preservation Trust website for more information.
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Tickets to the Strand Theatre vary in price depending on the event. Visit the Strand Theatre website for more information.
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Tours are fully refundable up to 24 hours in advance.
If it’s within 24 hours or you had an issue during your tour, email support@drivesanddetours.com. We review all requests individually and will always do our best to make things right.
Our goal is to ensure every traveler has a great experience exploring with Drives & Detours.
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This is a one-way route of about 1.5 miles (2.5 km) around Oak Bluffs. Walking it comfortably takes around an hour and a half, allowing time to pause, explore, and enjoy the surroundings at a relaxed pace.
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Yes, downloading the Drives & Detours app will give you full access to the tour you have purchased, as well as many other self-guided tours.
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Download the tour before you go. Some areas have poor signal, which can make downloading the tour difficult. Once the tour is downloaded, it will work without any cell signal
The tour audio plays automatically as you approach each stop
Want to see more? Tap “View Stop” to see photos and bonus content
To return to the map, tap the small down arrow between the “previous” and “next” buttons
Follow the blue line and audio directions to stay on route
Use audio controls to pause, rewind, or skip—just like a podcast
Safety first: Keep your eyes on the road or sidewalk, follow traffic laws, and stay aware of your surroundings
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No—download your Oak Bluffs tour before you go, and you won't need a cell signal. Drives & Detours’ tours work without any cell signal once they are downloaded to your device.
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Once you have purchased your Oak Bluffs walking tour from Drives & Detours, you can use it whenever you want. You can always take the tour another day if the weather is bad on the day you plan to take it.
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Unfortunately, Dives & Detours cannot guarantee that the Harpers Ferry self-guided tour is accessible. People with wheelchairs, strollers, or mobility impairments are very welcome, but we recommend checking the MVacay website for detailed information.
Pro Tips for Your Drives & Detours Oak Bluffs Self-Guided Tour
Download before you go.
Enable location services—GPS triggers the audio.
Use earbuds, headphones, or your car speakers.
Pause and resume anytime. If you take a break, just reopen the app and head back toward your last stop.
Lost your way? Tap any pin on the map, then tap the right-turn-arrow icon to open your default maps app for turn-by-turn directions to that spot.
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