Oak Bluffs Marina and Harbor in Winter: A Walking Guide

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 all but empty, the seasonal restaurants are shuttered, and the town goes from summer resort to a quiet village you can walk end to end.

Filmed February 2022The island moves on: shops, signs and prices may differ from what you see here. The text of this guide was checked September 2026.

The Marina in Winter

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 a stark, quiet 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 VTA bus every 60 to 90 minutes (fare-free through June 30, 2027)).

Year-round restaurants keeping Oak Bluffs alive:

• Offshore Ale Co.: craft beer, pizza, fireplace. Genuinely cozy in winter.
• Highlands General: the year-round market and cafe that took over the old Linda Jean's space in 2026, good for breakfast and lunch.
• Sharky's Cantina: Tex-Mex and margaritas, year-round.
• The Ritz: the Circuit Ave dive bar, 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.

A Winter Walking Route

Start at Ocean Park, a seven-acre green overlooking Nantucket Sound, with a white Victorian bandstand topped by a copper whale weathervane. In winter, Canada geese cover 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 empty: bare pilings, vacant moorings. The Summercamp Hotel (originally the Wesley Hotel, built 1879 for $18,000, now 95 rooms after a 2016 renovation) stands over the harbor with its long 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 about 1,400 (rated capacity roughly 1,700), National Historic Landmark since 2005) rises against the sky.

Return via Circuit Avenue for warmth at Highlands General 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 one island town where Black visitors could count on being welcomed at inns and guest houses 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 one of the best-known Black summer communities in the country. Dorothy West, Adam Clayton Powell Jr. and Martin Luther King Jr. all spent summers here, and the Obamas have vacationed on the island most summers since 2009. 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.