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Main Street in Vineyard Haven is where the Steamship Ferry arrives on Martha's Vineyard. Shops, restaurants and local businesses line the road up from the dock.
Vineyard Haven's Main Street is the island's year-round shopping street, and it feels different from Edgartown or Oak Bluffs. Edgartown is polished, with its whaling captains' houses, and Oak Bluffs' Circuit Avenue is built around the summer crowd and the nightlife. Vineyard Haven is a working town with an arty, local feel, and many of its businesses stay open all year.
Filmed June 2021The 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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The street clock on Main Street, with the sign for the public restrooms below it. Bunch of Grapes and Brickman’s are a few doors along.
Toccopuro and Co. in September, open from 6 AM, with tables out front under the green awning.
A.E. Kirkpatrick Jewelry Design and Creekville Art and Antiques share the shopfront at 9 Main Street, near the Five Corners end.
Bee Blunt at 75 Main Street, with two outfits in the windows and the door open.
A sandwich board on the brick sidewalk outside a Vineyard Haven steakhouse, open for breakfast, lunch and dinner; the year-round places advertise all three meals.
Flowers and a yellow umbrella outside Althea Designs, one of the small shops that give Vineyard Haven its arty, local feel.
The Black Dog Tavern by the harbor in Vineyard Haven, its black dog sign on the post and the water just beyond.
A mileage sign pointing up-island: West Tisbury 8, Chilmark 11, Aquinnah 18.
The foot of Main Street on the nor’easter Saturday, seen from beside the Mansion House, running down to a flooded Five Corners, a police cruiser with its lights on and a Detour Ahead sign at the bottom.
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From the ferry terminal on Water Street, Union Street takes you up to Main Street. The house numbers start low at the Five Corners end, by the Mansion House, and climb as you go: Brickman’s at 8, Toccopuro at 15, Bunch of Grapes at 23, the Capawock Theatre at 43, LeRoux and Rainy Day in the 60s, The Green Room at 71 and Waterside Market at 82, which calls itself the top of Main Street.
Planters along the sidewalk and a steady line of traffic on Main Street.
The Green Room’s fish sign over the path beside its stone building at 71 Main Street, with hydrangeas in bloom.
The Capawock has been dark for a while, and films now play at the Martha’s Vineyard Film Center at Tisbury Marketplace on Beach Road, which bills itself as a year-round cinema. A block west of Main, William Street is lined with Greek Revival houses built between 1833 and 1858 for mariners and builders, a historic district on the National Register. On Spring Street, the 1844 church that is now Tisbury Town Hall has the Katharine Cornell Theatre upstairs, named for the actress, and the Martha’s Vineyard Playhouse at 24 Church Street, now part of Circuit Arts, keeps a calendar of plays and music.
The William Barry Owen bandstand in Owen Park, with the harbor behind it.
Further along, Owen Park slopes from Main Street down to the harbor: a small beach, the town pier, the 1962 bandstand, swings and public restrooms. The pier was rebuilt and reopened in June 2026, wider, taller and easier to get onto. The land came from the family of William Barry Owen, who was born on Main Street in 1860; his widow gave it five years after his death in 1919. At 200 Main Street, the Vineyard Haven Public Library reopened on July 21, 2026 after a renovation and is open Tuesday to Thursday 10 AM to 6 PM, Friday 1 to 5 PM and Saturday 10 AM to 5 PM, closed Sundays and Mondays for now.
New this year: The Stitchery MV, a needle-arts studio, opened at 19 Main Street, and a Martha’s Vineyard Made pop-up with island artists is open through New Year’s Eve. Island Music and the Vineyard Haven Murdick’s Fudge Closed In October 2026 the company announced that its three island shops are closed; the fudge is still sold online. have closed, and Mocha Mott’s old building is now Toccopuro.
Vineyard Haven after dark in the holiday season, the shop windows lit; the December First Friday is the one that happens in the dark.
First Fridays are free outdoor arts nights on the first Friday of each month, June through October, plus December. Local makers set up a daytime art market downtown (10 AM–2 PM), and from 5 PM there are food trucks, live music and evening activities at Owen Park, often with a silent DJ party on the beach later; firstfridayvh.com posts each month's lineup. The next one is Friday, December 4, 2026; its lineup isn't out yet. Most of the town turns out.
A chalkboard at the First Friday artist market on Beach Street Extension in July 2026: art, cheaper than a yacht.
Island makers’ tables at the July First Friday, with a Martha’s Vineyard Made sign out front.
Tisbury went dry in 1834, almost a century before Prohibition. Restaurants were BYOB for decades. A 2008 ballot vote on beer and wine tied 690–690, a hand recount left the tie in place, and the measure failed. After that, voters approved alcohol step by step: beer and wine at restaurants in 2009, full liquor in 2017, and drinks without food in 2022. Restaurants now serve beer, wine and full liquor, and Chilmark is the last dry town on Martha's Vineyard.
On Saturday, August 11, 1883, at about 8:45 PM, fire broke out in R. W. Crocker’s harness factory on the east side of Main Street. A northeaster of about 30 miles an hour pushed it down both sides of the street. The town had no fire department and one telephone, at Luce’s store, which was used to call Cottage City (now Oak Bluffs) for help. By morning the Baptist church and the Mansion House were gone; one count lists 32 houses, 26 stores, 12 barns and 2 stables, another puts it at 72 buildings over more than 40 acres. Crocker started rebuilding while the timbers were still smoldering.
The village had changed its name only twelve years before. It was Holmes Hole until February 21, 1871, when the post office became Vineyard Haven. The town is still Tisbury; Vineyard Haven is the village and the postal address.
The library’s new covered entrance, with ribbons from the July 2026 reopening still on the posts.
Vineyard Haven is the island's year-round ferry port, and the Steamship Authority terminal is steps from Main Street. Getting around without a car is easy on the VTA bus, which is fare-free through June 30, 2027.
Cyclists crossing at the corner of Water Street, with the post office behind them and the mileage sign on the left: Oak Bluffs 3, Edgartown 8, West Tisbury 8, Chilmark 11, Aquinnah 18.
Exploring the town? Start with our complete Vineyard Haven guide: food, beaches, parking and the local rhythm, all in one place.
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. Steps. The Steamship Authority terminal sits at the bottom of town, so you can walk off the boat and be at Bunch of Grapes or the Black Dog Tavern within minutes. Vineyard Haven is the island's year-round port, which is why the street stays busy in winter. Our ferry guide has the schedules.
Street parking in town is free but time-limited and tight in summer. For a longer stay, the Tisbury Park and Ride on High Point Lane is open all year: free for stays of up to three days, or $2 for every day on a longer stay, with a VTA bus into town. In the center, the Beach Street lot by the old fire station costs $2 an hour from 8 AM to 8 PM with a four-hour limit, is free from 8 PM to midnight and has no overnight parking. Every lot is listed in our parking guide.
Yes. The town was dry from 1834, but voters approved beer and wine at restaurants in 2009, full liquor in 2017, and service without food in 2022. Chilmark is now the island's last dry town. Our dry towns guide explains the rules for each town.
First Fridays run June through October, plus one in December. October's was on the 2nd, so the last one of 2026 is December 4. The daytime art market goes 10 AM to 2 PM, and the food trucks and evening program at Owen Park start at 5 PM. Everything is free.
Mostly, yes. Vineyard Haven is a working town. The Green Room, Waterside Market, The Attic and the Black Dog Tavern all say they’re open year-round, and most other shops post daily hours that shrink in winter, so check before a special trip. Mad Martha’s ice cream is seasonal; in 2026 the Vineyard Haven shop is open through Sunday, November 1. See our off-season guide.
Inside the Steamship Authority terminal on Water Street (open every day), in the Water Street parking lot across from the police station and at Owen Park.
Toccopuro and Co. at 15 Main Street opens at 6 AM with coffee, breakfast and lunch. Delicious MV has French pastries and coffee, and Waterside Market at 82 Main Street runs a year-round cafe. For dinner ideas, see our restaurant guide.
Joshua Slocum, first to sail alone around the world, spent his last years farming in West Tisbury and vanished from Vineyard Haven harbor in November 1909. The voyage, the farm called Fag End, the last departure, and what a visitor can actually see: the harbor, a marker stone by a country road, the museum's Slocum papers, and the book itself.
The red bus that gets the loudest cheer in the Edgartown Fourth of July parade belongs to Camp Jabberwocky, a tuition-free summer camp for people with disabilities that has run on the Vineyard since 1953. An islander's account of where it came from and what it is. For anything official, the camp's own site is the source.
Lake Tashmoo in Vineyard Haven hides a century of stories: the 1887 waterworks that watered the town, a golf course where a bull was a hazard, town baseball and the frozen winters when islanders raced ice boats.
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.
The complete guide to Vineyard Haven, Martha's Vineyard's year-round port town. Main Street shopping, Black Dog Tavern, Owen Park, and ferry terminal.
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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