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Offered languages
- English
- English
Unearth the charm of Oak Bluffs on this self-guided walking tour, where the rich history and vibrant culture of this New England seaside town come alive.
Wander among whimsical gingerbread cottages, enjoy stunning harbor views, and learn how this area evolved from a Methodist camp meeting site to a celebrated resort.
This tour highlights the unique blend of architecture, community spirit, and African American heritage that defines Oak Bluffs, making it a delightful exploration of summer memories and local stories.
— Discover the distinctive Victorian architecture and intricate cottages
— Explore the historical significance of Oak Bluffs as a cultural hub
— Enjoy scenic ocean views and shaded park paths during your stroll
— Perfect for history buffs and those seeking a unique coastal experience
What's Included
Meeting and pickup
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.
Inkwell Beach runs along Seaview Avenue to the south of Oaks Bluff. The tour ends at the corner of Seaview and Tuckernuck Avenue.
Itinerary
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1
Step inside this tiny museum to see what life was like in a 19th-century “gingerbread cottage,” complete with original furnishings and period charm. The adjoining shop offers locally made crafts and souvenirs that capture the whimsy of Oak Bluffs.
5 minutes • Admission ticket free -
2
The lively heart of Oak Bluffs, Circuit Avenue, hums with summer energy, from old-fashioned ice cream parlors to boutique shops and cafés. It’s the perfect place to stroll, people-watch, and soak up the festive Vineyard atmosphere.
5 minutes • Admission ticket free -
(Pass by)
Perched high above the Sound, East Chop Lighthouse offers panoramic views of Vineyard Haven Harbor and the open sea. Its classic white tower has guided mariners since the 19th century and remains a symbol of the island’s maritime spirit.
Admission ticket free -
(Pass by)
Built in 1876, this hand-carved carousel is the oldest of its kind still operating in America. Take a spin and reach for the brass ring—an enduring Oak Bluffs tradition that delights kids and adults alike.
Admission ticket free -
3
A Vineyard institution since 1930, Giordano’s serves up golden fried clams and family-style Italian dishes just steps from the beach. It’s a taste of local history with every crispy bite.
30 minutes • Admission ticket free -
4
Beloved for its calm waters and deep cultural roots, Inkwell Beach has long been a gathering place for the island’s African American community. Its nickname—once pejorative—now stands as a proud symbol of heritage, resilience, and joy.
5 minutes • Admission ticket free -
5
With sailboats bobbing in the water and restaurants lining the docks, Oak Bluffs Harbor buzzes with seaside charm. By day, it’s a tranquil marina; by night, a lively waterfront scene with music and laughter spilling into the salt air.
5 minutes • Admission ticket free -
6
This open green bordered by Victorian houses and the sea is the town’s front porch—a favorite spot for kite flyers, picnickers, and evening strollers. Its central gazebo and sweeping views make it the backdrop for many summer celebrations.
5 minutes • Admission ticket free -
7
Wander through rows of brightly painted cottages adorned with intricate woodwork and storybook porches. Each home tells part of the town’s origin as a 19th-century Methodist camp meeting ground turned summer dreamscape.
5 minutes • Admission ticket free -
8
At the heart of Wesleyan Grove stands the Tabernacle, an iron-framed open-air pavilion built in 1879 for worship and community gatherings. Today, it hosts concerts, events, and the dazzling Grand Illumination Night, when hundreds of lanterns light up the evening sky.
5 minutes • Admission ticket free -
9
This octagonal, shingle-clad chapel has welcomed worshippers and visitors of all denominations since 1870. Its simple beauty and open design reflect the island’s spirit of inclusion and community.
5 minutes • Admission ticket free -
10
A broad, breezy field between Ocean Park and the sea, Waban Park hosts summer festivals, kite shows, and family picnics. Its open expanse is ideal for soaking in island sunshine or catching a cool Atlantic breeze.
5 minutes • Admission ticket free -
(Pass by)
This dynamic cultural museum celebrates the African diaspora through art, history, and storytelling. It’s a space for reflection and inspiration, highlighting voices and experiences often left untold in traditional narratives.
Admission ticket free -
11
Stretching two miles between Oak Bluffs and Edgartown, this barrier beach offers both gentle pond waters and rolling surf. It’s the ideal spot for swimming, sunbathing, or spotting the iconic Jaws Bridge.
5 minutes • Admission ticket free -
(Pass by)
Once a bustling 20th-century movie house, the Strand Theatre is a landmark of Oak Bluffs’ entertainment past. Though its marquee now marks a new chapter, it remains a nostalgic reminder of summer nights gone by.
Admission ticket free -
12
Easily accessible and family-friendly, this sandy beach offers calm swimming and picture-perfect harbor views. It’s a favorite for both day-trippers and locals looking to unwind steps from town.
5 minutes • Admission ticket free -
(Pass by)
This striking Gothic Revival cottage—known for its intricate trim and towers—has been lovingly restored after a devastating fire. It stands as a testament to Oak Bluffs’ enduring craftsmanship and charm.
Admission ticket free -
(Pass by)
Built in the 1920s by Harlem entrepreneur S. J. Overton, Villa Rosa became a gathering place for Black artists, thinkers, and vacationers. Its legacy as a beacon of community and culture still resonates through Oak Bluffs today.
Admission ticket free
Additional info
- Suitable for all physical fitness levels
- Works entirely offline once downloaded—no cell service required
- GPS-triggered audio plays automatically based on your location
- Flexible - Buy once, use any day/time—access never expires
- Get the Drives & Detours app download the tour ahead of time
Tags
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Show more
Cancellation Policy
- For a full refund, you must cancel at least 24 hours before the experience’s start time.
- If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the experience’s start time will not be accepted.
Rating
You can cancel up to 24 hours in advance of the experience for a full refund.
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