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.
The Oak Bluffs Marina, the largest marina on Martha's Vineyard, sits in a former landlocked lake called Lake Anthony, connected to Nantucket Sound through a dredged channel flanked by two granite breakwaters completed in 1899. In winter, the harbor is essentially empty, the seasonal restaurants shuttered, and the town transforms from a bustling resort into a serene, walkable village.
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The Marina in Winter
With the boats hauled and the crowds gone, the Oak Bluffs marina turns quiet and stark. Bare pilings, still water, and the light low over the Sound.
The town-owned marina at 10 Circuit Avenue Extension offers roughly 80 slips and 50 moorings, handling about 10,000 transient boats per season. But in winter, it's effectively empty: a 2023 Select Board vote prohibited overnight stays longer than 72 hours from December through April, ending the practice of boats wintering over. Only registered commercial fishing boats are exempt. The bare pilings and vacant mooring field make for a striking, meditative scene.
In summer, boats back in stern-to against the bulkhead, and crew climb a four-to-five-foot ladder to reach the walkway. It can handle yachts up to 115 feet. Slip rates run $5.00 per foot per night. The marina operates mid-May through mid-October. Current harbormaster: Emily DeBettencourt (508-693-4355).
What's Open in Winter
The Steamship Authority does not serve Oak Bluffs in winter; all ferries run to Vineyard Haven only. From there, it's 3 miles via Beach Road (6 minutes by car, or the free VTA bus every 60-90 minutes).
Year-round restaurants keeping Oak Bluffs alive:
- Offshore Ale Co.: craft beer, pizza, fireplace. Genuinely cozy in winter.
- Linda Jean's Restaurant: 40-year Circuit Avenue institution for breakfast, lunch, dinner.
- Sharky's Cantina: Tex-Mex and margaritas, year-round.
- The Ritz: beloved dive bar on Circuit Ave, live blues (Johnny Hoy twice weekly).
- Winston's Kitchen: Caribbean comfort food on the harbor's west side.
- The Barn Bowl and Bistro: restaurant plus 10-lane bowling alley.
Closed in winter: Nancy's Restaurant (reopens May), Back Door Donuts (mid-April), Flying Horses Carousel (mid-April). Check whatsopenonmv.com for current status. For a full restaurant guide see our complete dining guide.
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A Winter Walking Route
A loop around the harbor and up through the empty Campground is the classic cold-weather walk. Bundle up, because the wind off the water has teeth.
Start at Ocean Park, a seven-acre green overlooking Nantucket Sound, with a white Victorian bandstand topped by a copper whale weathervane. In winter, Canadian geese carpet the grass and you'll have the park to yourself. Walk north along Seaview Avenue past the 317-foot public fishing pier (opened 2014, wheelchair accessible, free) extending into the Sound.
Turn toward the harbor. The basin is strikingly empty: bare pilings, vacant moorings. The Summercamp Hotel (originally the Wesley Hotel, built 1879 for $18,000, now 95 rooms after a 2016 renovation) dominates the harbor skyline with its grand Victorian porches.
Cross Lake Avenue and enter the MVCMA campground through the wrought-iron arches. The gingerbread cottages (318 Carpenter Gothic houses painted in vivid maroon, teal, mustard, pink, and sky blue) are freely accessible year-round during daylight hours. In winter, you have them to yourself. The narrow lanes wind inward to Trinity Park, where the Tabernacle's wrought iron frame (built 1879, 130 feet across, seats 2,000, National Historic Landmark since 2005) rises against the sky.
Return via Circuit Avenue for warmth at Linda Jean's or Offshore Ale. The entire harbor-to-campground-to-Circuit Avenue loop takes under an hour.
The History Beneath the Paint
It all started on August 24, 1835, when Jeremiah Pease and six Edgartown Methodists pitched nine tents in an oak grove for a week of prayer. By 1868, there were 570. Tents became gingerbread cottages starting in 1859; the number peaked at ~500 around 1880.
The secular resort grew alongside. Businessman Erastus P. Carpenter hired Boston architect Robert Morris Copeland to design a planned community in 1866-67, one of the earliest planned residential communities in the United States. The area incorporated as "Cottage City" in 1880, renamed Oak Bluffs in 1907.
The African American connection runs deep. Oak Bluffs was the only town that accepted Black guests in its inns well into the mid-20th century. In 1912, Charles and Henrietta Shearer opened Shearer Cottage, the first inn for African American vacationers. By the 1930s, Oak Bluffs was the country's most exclusive African American vacation community. Notable figures: Dorothy West, Adam Clayton Powell Jr., Martin Luther King Jr., and Barack Obama. For the full story, see our Oak Bluffs complete guide.
For more on experiencing the island in winter, see our complete winter guide, or check current conditions on our live webcams.
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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.
