Oak Bluffs isn’t just a beach town—it’s a living scrapbook of stories, tradition, and charm. From its vibrant cottages to its deep-rooted cultural landmarks, there are so many fun and unexpected ways to explore the town’s past. Here are some of the best ways to soak in all the history of Oak Bluffs:
Wander the Gingerbread Cottages
A walk through Wesleyan Grove feels like stepping into a storybook. The pastel-colored “gingerbread” cottages are more than just pretty—they’re part of Oak Bluffs’ unique origin as a 19th-century Methodist camp meeting site. If you’re lucky enough to visit during Illumination Night, you’ll get to see the cottages glow with hundreds of paper lanterns. It’s magical.
Ride the Flying Horses
Yes, Oak Bluffs is home to the oldest platform carousel in the country! The Flying Horses Carousel has been delighting kids (and adults) since 1876. Try to grab the brass ring as you ride—it’s harder than it looks, but totally worth the bragging rights.
Discover Black History Along the Heritage Trail
Oak Bluffs has long been a treasured destination for African-American travelers, and the history here runs deep. Book a tour along the African-American Heritage Trail to hear about the people and places that shaped the community—from writers and civil rights leaders to iconic homes and historic beaches like the Inkwell.
Visit the East Chop Lighthouse
For the best view in town, head up to East Chop Light. This historic lighthouse offers sweeping views of the ocean and a quiet moment to reflect on all the stories this town has seen. Nearby, check out Union Chapel, an architectural gem that now hosts summer concerts and gatherings.
Join a Guided Tour or Event
From walking tours to themed bus rides, there’s no shortage of ways to hear Oak Bluffs’ stories come to life. Local guides are full of passion—and great tales—so even if you’ve been here before, you’re bound to learn something new.
Stay at Surfside Hotel
Now that you know history of Oak Bluffs, book a room at Martha’s Vineyard Surfside Hotel now that we’re open for the 2025 season! Nestled in the heart of Oak Bluffs, our dog-friendly hotel is one of the premier lodgings in the area. Choose from accommodations with ocean-view rooms, garden views, modern amenities, and enough space for the entire family. We are a short four-minute walk from Ocean Park and a convenient location for exploring the rest of the island!
Our seaside accommodations are proud to be family-owned and operated since 1987. We look forward to welcoming you and your family to your home away from home at Martha’s Vineyard Surfside Hotel. Book your vacation with us today!