• Cottage Museum - Explore this quaint museum to experience life in a 19th-century “gingerbread cottage,” complete with authentic furnishings and period charm. The nearby shop features locally crafted items and souvenirs that embody the whimsical spirit of Oak Bluffs.
• Circuit Avenue - The vibrant core of Oak Bluffs, Circuit Avenue, buzzes with summer excitement, offering everything from traditional ice cream parlors to boutique shops and cafés. It’s an ideal spot for a leisurely walk, people-watching, and enjoying the lively Vineyard atmosphere.
• East Chop Lighthouse - Situated high above the Sound, East Chop Lighthouse provides sweeping views of Vineyard Haven Harbor and the open ocean. Its iconic white tower has been guiding sailors since the 19th century and continues to symbolize the island’s maritime heritage.
• Flying Horses Carousel - Established in 1876, this hand-carved carousel is the oldest of its kind still in operation in America. Enjoy a ride and try to grab the brass ring—an enduring Oak Bluffs tradition that brings joy to both children and adults.
• Giordano’s Restaurant, Inc - A Vineyard staple since 1930, Giordano’s offers delicious fried clams and family-style Italian dishes just a short walk from the beach. Each crispy bite is a taste of local history.
• Inkwell Beach - Cherished for its tranquil waters and rich cultural significance, Inkwell Beach has long been a gathering place for the island’s African American community. Its once derogatory nickname now proudly represents heritage, resilience, and joy.
• Oak Bluffs Harbor - With sailboats gently swaying in the water and restaurants lining the docks, Oak Bluffs Harbor exudes seaside charm. By day, it’s a peaceful marina; by night, a vibrant waterfront scene with music and laughter filling the salty air.
• Ocean Park - This open green space, bordered by Victorian homes and the sea, serves as the town’s front porch—a beloved spot for kite flying, picnicking, and evening strolls. Its central gazebo and expansive views make it a backdrop for many summer festivities.
• Gingerbread Cottages - Stroll through rows of vividly painted cottages adorned with intricate woodwork and storybook porches. Each home narrates part of the town’s history as a 19th-century Methodist camp meeting ground turned summer paradise.
• MVCMA Tabernacle - At the center of Wesleyan Grove stands the Tabernacle, an iron-framed open-air pavilion built in 1879 for worship and community events. Today, it hosts concerts, gatherings, and the spectacular Grand Illumination Night, when hundreds of lanterns illuminate the night sky.
• Union Chapel - This octagonal, shingle-clad chapel has welcomed worshippers and visitors of all faiths since 1870. Its simple elegance and open design reflect the island’s spirit of inclusivity and community.
• Alley/Waban Park - A wide, breezy field between Ocean Park and the sea, Waban Park hosts summer festivals, kite displays, and family picnics. Its open space is perfect for soaking up island sunshine or enjoying a refreshing Atlantic breeze.
• Mariposa Museum - Oak Bluffs - This vibrant cultural museum celebrates the African diaspora through art, history, and storytelling. It offers a space for reflection and inspiration, highlighting voices and experiences often overlooked in traditional narratives.
• Joseph Sylvia State Beach - Spanning two miles between Oak Bluffs and Edgartown, this barrier beach features both calm pond waters and rolling surf. It’s the perfect location for swimming, sunbathing, or spotting the iconic Jaws Bridge.
• Strand Theatre - Once a bustling 20th-century movie house, the Strand Theatre is a landmark of Oak Bluffs’ entertainment history. Although its marquee now signals a new era, it remains a nostalgic reminder of past summer nights.
• Oak Bluffs Town Beach - Conveniently located and family-friendly, this sandy beach offers gentle swimming and stunning harbor views. It’s a favorite for both day-trippers and locals seeking relaxation just steps from town.
• Corbin Norton House - This remarkable Gothic Revival cottage—known for its intricate trim and towers—has been beautifully restored after a devastating fire. It stands as a testament to Oak Bluffs’ enduring craftsmanship and charm.
• The Overton House - Constructed in the 1920s by Harlem entrepreneur S. J. Overton, Villa Rosa became a hub for Black artists, thinkers, and vacationers. Its legacy as a beacon of community and culture continues to resonate in Oak Bluffs today.

• Unlimited access
• Audio guide
• App and tour download

• Smartphone (bring your own)

Discover the allure of Oak Bluffs with this self-guided walking tour, where the rich history and lively culture of this New England coastal town come to life.

Stroll among charming gingerbread cottages, take in breathtaking harbor views, and uncover how this area transformed from a Methodist camp meeting site into a renowned resort.

This tour showcases the distinctive mix of architecture, community spirit, and African American heritage that characterizes Oak Bluffs, offering a delightful journey through summer memories and local tales.

— Uncover the unique Victorian architecture and detailed cottages
— Delve into the historical importance of Oak Bluffs as a cultural center
— Relish scenic ocean views and shaded park paths during your walk
— Ideal for history enthusiasts and those looking for a unique coastal adventure

• 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

For a full refund, cancel at least 24 hours before the scheduled departure time.