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.
Circuit Avenue is the main commercial street and heart of Oak Bluffs, the most summer nightlife destination on Martha's Vineyard. Family-friendly by day with ice cream shops, fudge, and the carousel; a lively bar and music scene after dark.
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Circuit Avenue starts at the Flying Horses, the oldest operating platform carousel in the country, and runs down through the heart of Oak Bluffs.
At 33 Oak Bluffs Avenue, at the base of Circuit Avenue. Built in 1876 and originally at Coney Island; moved to Oak Bluffs in 1884. The oldest operating platform carousel in the United States, designated a National Historic Landmark in 1987. Features hand-carved horses with real horse-hair manes and tails, glass eyes, and the original brass ring game. Music by a 1923 Wurlitzer Band Organ. Summer hours: 10 AM–10 PM daily, rides $5 each. Celebrating its 150th birthday in 2026.
Restaurants
- Offshore Ale Co. (30 Kennebec Ave). Martha's Vineyard's only brewpub since 1997. Craft beers, wood-fired pizza, open year-round.
- Jimmy Seas Pan Pasta (32 Kennebec Ave). Italian pan pasta since ~1989, chef-owned, generous portions. Seasonal.
- Nancy's Restaurant (29 Lake Ave). Established c.1957. Waterfront seafood on the harbor. Reopening May 2026.
- Eleven Circuit (11 Circuit Ave). Full-service restaurant; breakfast through late night.
- Murdick's Fudge (5 Circuit Ave). Handmade fudge, family recipes from 1887. Temporarily closed as of mid-August 2026; check before visiting.
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Nightlife
- The Ritz Cafe (4 Circuit Ave). Historic dive bar and live music venue, established 1944. An Oak Bluffs landmark.
- Sand Bar and Grille (6 Circuit Ave Extension). Beach bar on the harbor with sand underfoot.
- The Lampost / Rare Duck (6 Circuit Ave). Martha's Vineyard's only nightclub with comedy shows, live music, and DJs.
Notable Changes for 2026
Linda Jean's Restaurant (25 Circuit Ave), the iconic Oak Bluffs diner operated for 47+ years, was sold in November 2025 for $4.9 million. Plans call for a new year-round fast-casual restaurant: breakfast, lunch, café/general store concept. Renovations targeted for completion by March 2026.
Circuit Avenue connects to Ocean Park, the large waterfront green with a Victorian bandstand, and is steps from the ferry terminal. See our Oak Bluffs Complete Guide (2026) for the full experience, or explore Inkwell Beach nearby.
Island Tip of the Day · Timing
Oak Bluffs restaurants are packed 6–8 PM. Eat at 5 PM or after 8:30 PM: same food, half the wait, easier parking.
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.
