The African American Heritage Trail of Martha's Vineyard: Sites, Stories and Tours (2026)
Shearer Cottage, Dorothy West, the Inkwell and 30 marked sites across the island: how to walk or tour the African American Heritage Trail of Martha's Vineyard.
Walk along the Oak Bluffs Pier, which is a spectacular sight on a gorgeous sunny day. You’ll see where the ferries dock in the summer, as well as where the local fishermen and women fish from the pier. A walk everyone must take while visiting Oak Bluffs on Martha’s Vineyard!
Location: Oak Bluffs, Martha's Vineyard , Massachusetts, USA
What to See at Oak Bluffs Pier and Harbor
The Oak Bluffs pier is the arrival point for ferries from Falmouth and Nantucket during the summer season, making it one of the liveliest spots on the island. From the pier, you'll see fishing boats heading out through the harbor mouth toward Nantucket Sound, and in the afternoon, local fishermen often line the railings hoping for striped bass and bluefish.
Looking inland from the pier, you'll spot the iconic Flying Horses Carousel, the oldest operating platform carousel in America, built in 1876. Just beyond is Circuit Avenue, the heart of Oak Bluffs' nightlife and shopping.
Extending Your Walk
From the pier, consider walking south along the seawall to Inkwell Beach, a historic beach with calm waters perfect for swimming. Or head inland two blocks to explore the Camp Meeting Association's Gingerbread Cottages: over 300 brightly painted Victorian homes surrounding the Tabernacle, an iron-frame open-air auditorium built in 1879. The full walking loop from pier to cottages and back takes about 45 minutes at a leisurely pace.
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Continue Exploring Martha's Vineyard
Exploring the town? Start with our complete Oak Bluffs guide: food, beaches, parking and the local rhythm, all in one place.
Island Tip of the Day · Timing
Visit Edgartown on a Tuesday or Wednesday. Same beautiful town, maybe 30% of the weekend crowds. Most restaurants have availability without reservations.
Disclaimer: The information in this article is provided for general guidance only and was accurate at the time of writing. Beach conditions, hours, prices, lifeguard schedules, ferry fares, and business operations change frequently and without notice. Ocean swimming carries inherent risks including rip currents, undertow, and cold water shock. Always verify current conditions with official local sources before your visit. MV Vacation assumes no responsibility for any loss, injury, or inconvenience resulting from the use of this information. Swim only where lifeguards are on duty, supervise children at all times near water, and follow all posted safety signs.
