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The seawall walk along Seaview Avenue in snow, the pier beyond and the water still.
Oak Bluffs Harbor in winter: empty marina, gingerbread cottages, year-round restaurants, and a quiet walking route through town.
The Oak Bluffs Marina sits in what was once Lake Anthony, a brackish pond with only a small natural opening to Nantucket Sound until a dredged channel flanked by two granite jetties was finished in November 1899. In winter the harbor is nearly empty and the seasonal restaurants are closed, and the town shrinks 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 October 2026.
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Ducks on the open water at the edge of the ice as the sun goes down behind the trees.
The town-owned marina at 10 Circuit Avenue Extension rents slips and moorings to visiting boats each season, booked through Dockwa. In winter it's close to empty: a 2023 Select Board vote barred overnight stays longer than 72 hours from December 1 to April 1, which ended the practice of boats wintering over, and only registered commercial fishing boats are exempt. What's left is bare pilings and an empty mooring field.
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 110 feet. Slips were $4 to $5 per foot per night in 2024 (the latest rates posted), and the marina runs from late May to about October 20. The harbormaster is Emily DeBettencourt (508-693-4355).
The Steamship Authority does not serve Oak Bluffs in winter; all ferries run to Vineyard Haven only. From there it's 3 miles along Beach Road: 6 minutes by car, or the VTA bus about every 30 minutes for most of the day on Route 13, fare-free through June 30, 2027.
These Oak Bluffs restaurants stay open all year:
Closed in winter: Nancy's Temporarily closed Closed for the season; reopening May 2027, per its own site Restaurant (reopens May), Back Door Donuts Temporarily closed Closed for the 2026 season; back in 2027, per its own site, window and front bakery alike (closed for the 2026 season, back in 2027), Flying Horses Carousel (open seasonally; the Vineyard Trust posts current hours). whatsopenonmv.com keeps the current status. Our complete dining guide has the rest.
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Salt spray frozen thick on the seawall after a hard cold snap, with the ferry pier in the distance.
Oak Bluffs after a snowfall, plowed and quiet by the water. A loop around the harbor and up through the empty Campground makes a good cold-weather walk, with a sharp wind off the water.
The walk starts 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. From there Seaview Avenue runs north past the 317-foot public fishing pier (opened 2014, wheelchair accessible, free) extending into the Sound.
Then the route turns toward the harbor basin. 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.
Across Lake Avenue, wrought-iron arches lead into the MVCMA campground. The gingerbread cottages (318 Carpenter Gothic houses painted maroon, teal, mustard, pink and sky blue) are open to walk past year-round in daylight, and in winter the lanes are nearly empty. They wind inward to Trinity Park, where the Tabernacle's wrought iron frame (built 1879, 130 feet across, seating about 1,400 with a rated capacity of roughly 1,700, a National Historic Landmark since 2005) rises against the sky.
Circuit Avenue brings you back, with Highlands General or Offshore Ale for warming up. The whole harbor, Campground and Circuit Avenue loop takes under an hour.
It 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.
Oak Bluffs also has a long African American history. It 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. Our Oak Bluffs complete guide has the full story.
Our complete winter guide covers the rest of the island in winter, and the live webcams show current conditions.
Step 1 · WhenMonth PickerTwelve months compared on NOAA numbers, crowds, prices and what is open. 
Step 2 · DaysDay-by-Day Trip PlannerMorning, afternoon and evening sketched for every day, events dropped in, emailed to you. 
Step 3 · CostTrip Cost CalculatorFerry, beds with the rooms tax, meals, getting around and activities in one price range. 
The Martha's Vineyard Songwriters Festival, September 17 to 20, 2026: a free kickoff at Nomans and three nights of Nashville writers at the Strand Theatre in Oak Bluffs, with our photographs from inside the Strand, the night-by-night lineups and practical notes for next year.
The Feast of the Holy Ghost in Oak Bluffs, held every third full weekend of July since 1928: the Queen Isabel legend behind the free soup, the Sunday parade from the ferry up Circuit Avenue, the crown blessed at Our Lady Star of the Sea, the sopas at the Portuguese-American Club, the club the rest of the year, and how a visitor should behave at the island's Portuguese feast.
East Chop Lighthouse in Oak Bluffs: the 1878 cast-iron tower on Telegraph Hill, the Sunday sunset openings run by the Martha's Vineyard Museum, the semaphore and Chocolate Lighthouse history, and the bus stop and parking below the hill.
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.
Take a guided Jaws tour of Martha's Vineyard with local guide Mike Currid. Walk the real Amity Island in Edgartown and book the “Amity” Walking Tour.
A first-hand look at the Edgartown Historic Walking Tour and “Amity” Jaws Tour with Mike Currid of the Edgartown Tour Company: what to expect, what you'll learn, and how to book.
Island tip of the day Timing No. 61 of 79 New tip at midnight, island time
Visit Edgartown on a Tuesday or Wednesday. Same beautiful town, maybe 30% of the weekend crowds. Most restaurants have availability without reservations.
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