By MV Vacation BlogUpdated 16 Sep, 2026Facts checked Aug 28, 202625 mins read 906 views
Vineyard HavenPhoto by MV Vacation
Main Street in Vineyard Haven, Martha's Vineyard.
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.
Vineyard Haven is the island's year-round town: the main ferry port, a working harbor with an arty streak, and the place where islanders actually live and shop twelve months a year. Three major new restaurants opened in 2025, the new Woods Hole terminal opened in June 2026 after a multi-year rebuild, and the dry-town era is officially over. This is the 2026 guide, top to bottom. A mile up the hill on Greenwood Avenue is Camp Jabberwocky, the tuition-free summer camp the island has run since 1953.
Filmed May 2021The island moves on: shops, signs and prices may differ from what you see here. The text of this guide was checked September 2026.
ArtCliff Diner, 39 Beach Road Temporarily closedClosed until further notice: the sign on the door and the diner's own website say temporarily closed as of 5 September 2026. No reopening date given.
Opened August 27, 2025 inside the former Martha's Vineyard National Bank, a grand stone building with a domed ceiling and stained-glass arches. Chef Marc Orfaly (seven-time James Beard nominee) runs coastal Mediterranean cuisine. The 9,000-pound bank vault door is now an eight-seat dining table; the vault itself serves as a wine cellar. Wed–Sun 4–11 PM. Fine dining ($$$$). Reservations via OpenTable; $50/guest cancellation fee.
Vineyard Haven · Ocean ClubPhoto by MV Vacation
The happy hour board at The Ocean Club door, framed by the old bank building's stone arches.
9 Craft Kitchen and Bar, 9 Main Street
Opened May 2024 in the former Copper Anchor space, adjacent to Mansion House Hotel. "New World cuisine" blending Asian, Peruvian, and Italian influences: cast-iron swordfish, lobster pappardelle. 130 seats. Entrées ~$25–50+. Off-season: Wed–Sat 4–9 PM. Phone: (508) 338-7431.
The Maker: Pasta Shop and Café, 339 State Road
Opened May 22, 2025, replacing the Little House Café. CIA-trained Chef Carlos Montoya, who formerly cooked for Presidents Obama and Clinton, makes seasonal handmade pasta. Lunch Tue–Sat 11 AM–3 PM; dinner Tue–Sat 5–9 PM. Retail shop sells pasta by the pound.
Vineyard Grill, 13 Beach Street Extension
The Five Corners room that was the Golden Bull and then, briefly, MV Tap is now a Brazilian steakhouse. Vineyard Grill is run by José Pedro dos Santos and Marcos Nascimento, who came from the Brazilian Grill in Hyannis: churrascaria-style beef, a signature pound-and-a-half top sirloin with yucca fries, a lunch buffet from 11 to 3, a full bar, and the Vineyard Bakery attached next door with Brazilian cakes. Open every day 7 am to 11 pm with breakfast, lunch and dinner menus (as reported in May 2026; confirm before a special trip).
Vineyard Haven · Five CornersPhoto by MV Vacation
The Vineyard Grill at Five Corners, blue shingles and a sandwich board on the bricks: Brazilian steakhouse, lunch and dinner, full bar, bakery attached. The two-hour parking sign means what it says here.
Notable Closures
Mocha Mott's VH (15 Main St): permanently closed January 18, 2026 after 20+ years. Co-owner Tim Dobel (76) retired. A customer appreciation day featured free coffee and an emotional farewell. The building was sold to Toccopuro, the island coffee chain with cafes in Edgartown and Oak Bluffs, and by early September 2026 Toccopuro and Co. was open in the space under a green awning: doors at 6 am, coffee, smoothies, bubble tea, breakfast and lunch, tables on the sidewalk. Oak Bluffs location continues. Copper Anchor, Little House Café, Model Deli: all closed, replaced by new concepts above.
Vineyard Haven · 15 Main StreetPhoto by MV Vacation
Toccopuro and Co. in the old Mocha Mott's building, September 2026: green awning, sidewalk tables and a 6 am start.
Restaurants with 2026 Prices
Black Dog Tavern, 20 Beach Street Extension
Founded 1971 by Captain Robert Douglas, a retired jet fighter pilot who sketched the building on a napkin. Named for his black Lab. Year-round. In season daily 7 AM–9 PM (breakfast until 3, raw bar 3–5, dinner from 5); off-season hours shrink to breakfast and lunch most days. Lobster roll, signature quahog chowder, Prime Rib Night (Thursdays, $29.95). Full bar.
Martha's VineyardPhoto by MV Vacation
Signpost surrounded by hydrangeas at the Black Dog in Vineyard Haven.
Waterside Market, 82 Main Street
Year-round since 2008. Daily 7 AM–5 PM. Clam chowder $9, sandwiches $9.75–20, lobster Benedict. Breakfast all day. Online ordering via Toast with curbside pickup.
The Attic, 82 Main Street, 2nd Floor
Above Waterside Market (NOT at Mansion House). Prohibition-era speakeasy vibe. Daily 3:30–10 PM. Smash Burger $21, Tuna Tartare $20, Crispy Brussels $16. Houses the largest bourbon collection on Martha's Vineyard.
Vineyard Haven · 82 Main StPhoto by MV Vacation
Waterside Market with The Attic glowing upstairs: Main Street after dark, striped awning and all.
ArtCliff Diner, 39 Beach Road
Operating since 1943. MV Magazine "Best Breakfast" perennial winner. The Old Faithful (2 eggs, meat, home fries, toast) $15. Three-egg omelettes $16–18.50. Creative daily specials. Mon/Thu–Sun 7 AM–2 PM. Year-round.
Vineyard Haven · 39 Beach RoadPhoto by MV Vacation
ArtCliff on 5 September 2026: closed until further notice, the sign says, with the 2026 Cape Cod Life Best Of sticker beside it. Check before you plan a breakfast around it.
Sandy's Fish and Chips, 5 Martin Road
Family-owned 75+ years. Seasonal: opens late April. Fish and chips, lobster roll, the "Obama Burger." Budget-friendly by MV standards. Mon–Sat 11 AM–7 PM.
Net Result, 79 Beach Road
Fish market + takeout + sushi bar since 1986. BYOB. Daily ~9 AM–7 PM. Ships seafood nationwide. Lobster roll ~$25–35.
Vineyard HavenPhoto by MV Vacation
The Net Result fish market at Tisbury Marketplace in Vineyard Haven.
Beach Road, 79 Beach Road
The dinner room at Tisbury Marketplace, sister restaurant to State Road in West Tisbury: New American cooking built on island seafood and produce, with a glassed-in porch looking over Lagoon Pond. Dinner Monday to Saturday from 5 PM; book ahead in season.
Vineyard Haven · Tisbury MarketplacePhoto by MV Vacation
Beach Road on a September morning: the shingled dinner house at 79 Beach Road, Lagoon Pond just behind the porch.
Scottish Bakehouse, 977 State Road
Founded 1961 from Scotland. Famous shortbread, Key lime pie ("best on island"), breakfast burritos, smash burgers. Mon–Sat 6 AM–6 PM; Sun 7 AM–3 PM. Has an on-site farm.
The Wave, 52 Beach Road
New for 2026: The Wave has taken over the marina waterfront spot that was Garde East, opening in mid-May. Same front-row harbor views, new name and new kitchen. It stepped straight into the island's event calendar too, hosting the closing-night party of the September film festival. Seasonal; check current hours before you go. Joshua Slocum, the first solo circumnavigator, sailed out of this harbor for the last time in 1909; the story is worth ten minutes.
Mikado Asian Bistro, 76 Main Street
Vineyard Haven's Asian bistro standby on upper Main Street. Its former Oak Bluffs outpost at 6 Circuit Avenue has become The Black Dog Pub (opened summer 2026, daily 7 AM to 10 PM), so Main Street is where you will find Mikado now.
Vineyard Haven · MikadoPhoto by MV Vacation
Inside Mikado on Main Street, where a mounted sailfish hangs over the dining room.
El Barco, 16 Union Street
Opened summer 2024 with outdoor Mexican street food overlooking the SSA terminal. 70 seats, tacos, burritos, and tequilas. A casual option steps from the ferry.
Not Your Sugar Mamas
All-vegan organic café serving açaí bowls, smoothies, and plant-based dishes. Year-round. The all-vegan option in town.
Porto Pizza, 36 Water Street
The slice counter a minute from the Steamship terminal, sharing the building with the Menemsha Blues shop: whole pies, slices, thin crust or deep dish, picnic tables under red umbrellas out front, and evening delivery down-island (508-693-6200). The place to eat a cheese slice while the ferry line moves.
Vineyard Haven · 36 Water StreetPhoto by MV Vacation
Porto Pizza's tables outside Menemsha Blues on Water Street, with the sign that keeps the tractor trailers off the harbor lane.
Sweet Bites, 32 Beach Street
Family-run small-batch bakery and cafe with American and Brazilian sweet and savory things: coffee and espresso, breakfast and lunch sandwiches, tarts and pies, acai bowls, custom cakes. Pink door, no pets, and the case empties early on a ferry morning.
Vineyard Haven · 32 Beach StreetPhoto by MV Vacation
Sweet Bites on Beach Street: cakes, pies and Brazilian pastries behind the pink door, a short walk from the ferry.
S and S Kitchenette, 48 Main Street
Prepared meals to go by day, chef dinners and classes some evenings, and a proper coffee bar at the front under a green ceiling of glassware and teapots. The board in September 2026 read drip coffee $4, cappuccino $5, latte $5.50, matcha or a London Fog $6, plus boozy coffee, house wine and beer. Hours shift with the events calendar, so check the door.
Vineyard Haven · 48 Main StreetPhoto by MV Vacation
The coffee bar at S and S Kitchenette: the menu board, the cake case and a shelf of cookbooks under the counter.
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Shopping on Main Street
Bunch of Grapes Bookstore (23 Main St): Founded in 1964, one of the best-known independent bookstores in the country. In 2008, a devastating fire at neighboring Café Moxie destroyed the store's interior. Historian David McCullough said: "If there should be no Bunch of Grapes, where would Vineyard Haven's Main Street be?" The store rebuilt and reopened across the street. In September 2022, Molly and Brendan Coogan purchased the store. President Obama visits for his summer reading list. The store is also a stop on the Jaws filming locations tour. Year-round with author events.
Brickman's (south end of Main St): A Vineyard institution since 1913. Clothing, footwear, sporting goods, and toys in a "Tardis of a store" that is far larger inside than it appears.
C.B. Stark Jewelers (53A Main St): The island's go-to for Martha's Vineyard charms, custom work, sea glass jewelry, and wampum. Over 40 years in business.
Rainy Day (66 Main St): Boutique gift shop founded in 1973, now owned by Melissa and Bob Scammell. Cards, home decor, jewelry, candles, toys, and MV-themed items. Celebrated its 50th anniversary in 2023. Also has an Edgartown location.
LeRoux at Home (62 Main St): Three floors of kitchen goods, tableware, and home decor, with companion shop LeRoux Gourmet across the street.
The Seven Sisters (19 Main St): Recognized by Boston Magazine's "Best of Boston" for clean/green shopping and independent artisan goods.
Martha's Vineyard Made (29 Main St): A collaborative shop for local artisans selling pottery, prints, jewelry, and pantry items.
Lennox and Harvey General Goods: Opened in 2024 with curated home goods and furniture, founded by Mark Chung and Eric Coles from Brooklyn.
Nearly every shop on Main Street is independently owned; the island has actively fought to exclude chain stores.
Out of the center, on State Road past Cronig's, Second Nature at Eden (427 State Road) is the garden center that reopened under new ownership in 2025, with native plants outside and a gift shop, the She Shed, stocked with local honey, seeds and island-made things. Seasonal, into mid-October.
Vineyard Haven · State RoadPhoto by MV Vacation
The She Shed at Second Nature at Eden: baskets in the rafters, local honey, seeds, island artists and the autumn stock arriving in early September.
For the other kind of shopping, the Thrift Shop on Chicken Alley (38 Lagoon Pond Road, off Beach Road) has been raising money for Martha's Vineyard Community Services since 1962 and is the island's best rummage: clothes, books, kitchenware, furniture, bikes. The hours on the door are Tuesday 10 to 7, Wednesday to Friday 10 to 5, Saturday 10 to 4, closed Sunday and Monday, and customers park at Veterans Park across the road. Our shopping guide has the rest of the island's thrift circuit.
Vineyard Haven · Chicken AlleyPhoto by MV Vacation
The door at Chicken Alley: hours in English and Portuguese, a bell, and the customer parking sign pointing across to Veterans Park.
The Great Fire of 1883
On August 11, 1883, fire started at a harness factory on Main Street. With no fire department, no fire engine, and only a few antiquated buckets, the town watched as 60+ buildings burned in six hours: 32 houses, 26 stores, the Baptist Meeting House, and the Mansion House hotel. A 30 mph northeaster drove flames through tinder-dry wooden buildings. Total losses: $200,000 (~$6.5 million today). No one died. The Tisbury Fire Department was established in 1885 as a direct result.
William Street Historic District
One block west of Main Street, this district was added to the National Register of Historic Places in 1983 and contains 56 contiguous properties along William, Spring, Church, Franklin, and Main Streets. Most houses were built 1830–1860 in Greek Revival style by sea captains, merchants, and builders. The district survived the 1883 fire, making it the town's oldest surviving neighborhood. It includes the Playhouse, Tisbury Town Hall, the Proprietor's Burying Ground (dating to 1770), and several historic churches. A quiet walk past big old houses under old shade trees.
Vineyard Haven · William StreetPhoto by MV Vacation
William Street on a September afternoon: fieldstone walls, the old trees, a church with an arched window and the houses the 1883 fire never reached. The whole district is on the National Register.
From Dry Town to Full Bar: The Timeline
Tisbury was dry since 1834. In 2008, a vote to allow beer/wine tied exactly 690–690 and failed (made national news). Voters approved beer/wine in 2009, full liquor in 2017, and drinks without food in 2022 (68% support). Today restaurants serve full liquor, but still no liquor stores or standalone bars. Chilmark is now the only dry town.
Events
Vineyard HavenPhoto by MV Vacation
First Friday banners on the lamp posts along Main Street.
First Friday. 2026 dates: June 5, July 3, August 7, September 4, October 2, December 4. Art market with 30+ makers, live music, food trucks, beach bonfire, silent disco (9–11 PM). Free. Daytime market from 10 AM, evening program 5–11 PM at Owen Park and Main Street.
Vineyard Haven Band: Founded 1868 by 18 returning Civil War veterans. Originally called the "Vineyard Haven Silver Cornet Brass Band," the band performed for President Ulysses S. Grant during an 1874 visit and celebrated its 150th anniversary in 2018. Today, 15 core musicians and 20+ seasonal players (ages 7 to 84) perform free Sunday evening concerts at 8:00 PM in July and August at Owen Park, alternating with Ocean Park in Oak Bluffs. Believed to be America's second-oldest continuously performing concert band.
Arts and Culture
Martha's Vineyard Playhouse, 24 Church Street
Built in 1833 as a Methodist Meeting House, this building has served as a town hall, Masonic lodge, and since 1982, a working theater. A complete renovation in 2011–2014 added a new lobby and full accessibility. Now a professional nonprofit working theater operating year-round with an intimate ~112–150 seat black-box space (the Patricia Neal Stage). Monday Night at the Movies screens classics at $5 cash at the door. Military get free tickets; EBT/WIC holders pay $15. Phone: (508) 696-6300.
Capawock Theatre, Main Street
Opened in March 1913 as the Vineyard Theatre, renamed Capawock in 1932. The oldest continually operating movie theater in Massachusetts, when it was operating. Renovated with over $1 million and reopened May 29, 2015 with a ceremony featuring Carly Simon. The MV Film Society ran it, showing 200+ films to 35,000+ patrons annually. Dark for most of the 2020s after COVID and streaming shifts ended regular operations, the building was sold to new owners in February 2026 and has started hosting screenings again (the spring film festival used it in March 2026); check locally for the current schedule. The MV Film Society now operates from its own Film Center at Tisbury Marketplace.
Art Galleries
Louisa Gould Gallery (54 Main St) is the anchor, established in 2003 and voted "Best MV Gallery." The annual Small Wonders Holiday Show is a highlight. Kennedy Studios / Island Art Gallery (66 Main St) offers photographs, original art, and custom framing. Blue Fathom Gallery features work by several island artists. Most galleries operate seasonally with expanded summer hours, all within the designated Vineyard Haven Harbor Cultural District.
Vineyard HavenPhoto by MV Vacation
Vineyard Haven with Martha's Vineyard Museum visible in the background.
The museum's boat shed, across the courtyard from the main building, holds the working end of the collection: a whaleboat, ship models, a carved wooden battleship, the wheel of the steamer Uncatena. Outside on the grounds stands Sunbird, Tim Laursen's 2020 kinetic sculpture, whose wings flap faster the stronger the sun and slower when you take over with the hand crank, a gift of the South Mountain Company.
Vineyard Haven · MV Museum boat shedPhoto by MV Vacation
The boat shed: a carved battleship, a whaleboat and a row of ship models under the rafters.
Vineyard Haven Public Library
After a year-plus renovation that added a new meeting room, the library reopened at its permanent 200 Main Street home in July 2026. Summer hours, posted at the door and on vhlibrary.org: Tuesday to Thursday 10 AM–6 PM, Friday 1–5 PM, Saturday 10 AM–5 PM, closed Sunday and Monday (Sunday hours are due to resume after Labor Day; check vhlibrary.org for the fall schedule). The library holds 42,680 volumes and circulates 134,790 items per year. Programs include Storytime with Weezie, Lego Build Club, book groups, and author talks. Dogs are not allowed inside except service animals, under the Town of Tisbury policy. Director: Amy Ryan. Phone: (508) 696-4210.
Vineyard Haven · 200 Main StreetPhoto by MV Vacation
Inside the library six weeks after it reopened: new oak floors, the stacks back in place and the summer hours posted at the desk.
Vineyard Haven · MV Museum groundsPhoto by MV Vacation
Sunbird's panel: turn the crank and see whether you can match a square foot of sunlight. On a cloudy day you can.
Beaches
Vineyard HavenPhoto by MV Vacation
Lake Tashmoo in Vineyard Haven.
Martha's VineyardPhoto by MV Vacation
Owen Park in Vineyard Haven.
Owen Park Beach: Calm harbor water, playground, lifeguards in summer, ADA accessible, swimming float, free. Steps from the ferry. The park has public restrooms, open-air showers, and a playground with swings. In December 2024, Tisbury secured a $1 million state grant for a complete pier replacement. The existing pier, never fully rebuilt in nearly a century, was "crumbling underfoot." The rebuilt Owen Park Dock with ADA-accessible ramps is confirmed for the 2026 boating season. Lake Tashmoo Beach (see our complete beaches guide). Dual swimming: freshwater lake + Vineyard Sound saltwater. 1 mile down a dirt road. Lifeguards in summer. Lake Tashmoo was freshwater until the 1938 hurricane opened a permanent channel to the ocean. The pond's longer backstory, from the Victorian waterworks to golf links and ice boats, has its own history piece.
Vineyard HavenPhoto by MV Vacation
Vineyard Haven Harbor full of boats on a summer day.
West Chop Lighthouse and Trails
The West Chop Lighthouse marks the northern tip of the West Chop peninsula, roughly 2 miles from downtown, about a 35-minute walk or a short bike ride north along Main Street. The current 45-foot brick tower dates to 1891, built 17 feet taller than its predecessor because large summer "cottages" had begun to obscure the light. The original fourth-order Fresnel lens still operates, flashing white visible for 15 miles. Added to the National Register of Historic Places in 1987.
West Chop is the only Martha's Vineyard lighthouse not open to the public: the property serves as Coast Guard quarters. You can view and photograph from the road. Parking is limited to street-side spots near the West Chop tennis courts on Franklin Street.
The West Chop Woods, a 90-acre conservation property managed by Sheriff's Meadow Foundation, offers 1.5+ miles of marked walking trails through some of the oldest forest on the island. The Red Trail follows an old cart path that once connected Vineyard Haven to the lighthouse. Trailhead parking is off Franklin Street, about 1¼ miles toward West Chop from downtown.
The West Chop neighborhood features rambling waterfront mansions from the 1890s–1900s with views over Vineyard Sound. Properties routinely list at $3–$11 million+.
Tennis and Pickleball
Tisbury runs two public court sites, and neither is a free-for-all in summer. The Church Street courts (50 Church Street, two unlighted clay courts, in play May through November) are booked through the town's CourtReserve system, which issues a gate PIN with the reservation; the town fee schedule lists $30 for a 90-minute slot, with the money going back into court upkeep. The Lake Street courts (Lake Street at Powell Lane) are the pickleball site, three hard courts with permanent lines and portable nets, $20 an hour by the same booking system, and the town runs youth clinics there. Questions go to the Parks and Recreation office, (508) 696-4220. If you want to play without a booking, the nearest walk-on courts are Niantic Park in Oak Bluffs.
Groceries and Everyday Essentials
Cronig's Market, 357 State Road
Founded in 1917 by four Lithuanian Jewish immigrant brothers: Sam, Ed, Henry, and Tebby Cronig. Sam arrived around 1905, reportedly the first Jewish person to settle on the island. In 2022, longtime manager Steve Bernier sold the business to Andrea Donnelly, the company's bookkeeper who started as a 15-year-old cashier, preserving island ownership. Cronig's was the first grocer on the East Coast to accept credit cards and one of the first to install solar panels with EV charging. Hours: Mon–Sat 7am–7pm, Sun 9am–6pm. Deli with prepared foods, organic and local products. Also operates a location in West Tisbury. Does not sell beer or wine. For packaged alcohol, go to Oak Bluffs (Tony's Market) or Edgartown.
Vineyard Haven · Main StreetPhoto by MV Vacation
The new cedar-shingled entrance and covered porch, still wearing the ribbons from the July reopening in early September.
Vineyard Haven · State RoadPhoto by MV Vacation
Cronig’s Market, the island’s year-round grocery anchor since 1917.
Stop and Shop, 50 Water Street
Directly across from the SSA ferry terminal: the most convenient grocery stop upon arrival. Full-service supermarket with produce, dairy, meat, deli and prepared foods (note: no pharmacy counter here; the Stop and Shop pharmacy is at the Edgartown store). Also operates a gas station at 86 Beach Road. Hours: Mon–Sat 6am–11pm, Sun 6am–10pm.
Ackee Tree Caribbean American Grocer (25 Beach Rd): a small yellow-doored shop stocked with Jamaican and Caribbean staples, salt fish, plantains and hard dough bread, plus hot patties and home-cooked food to go. It doubles as a neighborhood hub for the town's Caribbean families, and the patties are worth the stop.
One planning note while you are shopping: Vineyard Haven has no liquor store. Restaurants here pour beer, wine and cocktails with meals, and the odd shop may sell a limited bottle, but for a proper selection to take back to the rental you shop in Edgartown or Oak Bluffs, or have Our Market in Oak Bluffs deliver.
Vineyard Haven · Ackee TreePhoto by MV Vacation
The Ackee Tree Caribbean American Grocer on Beach Road: patties, plantains and island staples of a different island.
Vineyard Grocer, 294 State Road
30+ years in operation, offering fresh organic foods, daily-made meals, and Brazilian specialties alongside gourmet products. For every supermarket and market on the island with posted hours, see our grocery stores guide.
Mail and shipping
The post office is on Lagoon Pond Road. For FedEx there is a self-service drop box on State Road beside the Black Dog Bakery Cafe: the last weekday pickup is 3:30 in the afternoon, there is no pickup at all on Saturday or Sunday, and the box holds no supplies, so bring the package packed and labeled. A staffed FedEx Authorized ShipCenter, The Mailroom, is at 243 Edgartown to Vineyard Haven Road on the Edgartown side. Anything dropped after the Friday pickup leaves the island on Monday, which is worth knowing if you are shipping a rental key or a forgotten passport. One more thing, new in September 2026: a notice on the post office door says a parcel addressed to a street with no mailbox and no PO Box is returned after one day, so ask a clerk about a PO Box or rural delivery if you expect packages.
Vineyard Haven · State RoadPhoto by MV Vacation
The FedEx drop box on State Road: last pickup 3:30 on weekdays, none at the weekend, and the holiday schedule printed on the lid.
For UPS, and for anything that needs packing, printing or a notary, The UPS Store is at 455 State Road in the Woodland Business Center, the shingled building with the cupola about a mile out of town on the way to the airport (VTA Route 3 runs along State Road). The hours on the door are 8 to 6 on weekdays and 9 to 3:30 on Saturday and Sunday, the useful part being the weekend. It also takes Happy Returns drop-offs, and AARP and AAA members get a discount on services. Phone 508-696-0600.
Vineyard Haven · 455 State RoadPhoto by MV Vacation
The UPS Store in the Woodland Business Center: open seven days, weekends included.
Parking
Tisbury Park and Ride (High Point Lane): Free for 3 days or less, then $2/day. Free VTA shuttle to ferry (~5 min, every 20 min). Old Fire Station Lot (Beach Street): $2/hour, 4-hour max. Main Street: 2-hour limits. Best advice: don't bring a car.
Five Corners
The island's most confounding intersection: five roads converge with no traffic light and no rotary. Two blocks from the ferry terminal. Beach Road has right-of-way. Police direct traffic only when ferries arrive. Locals depend on "politeness and whatever mood you're in." MassDOT is studying a redesign including a possible roundabout.
Vineyard HavenPhoto by MV Vacation
Five Corners intersection in Vineyard Haven.
Holmes Hole to Vineyard Haven
Vineyard HavenPhoto by MV Vacation
The original name "Holmes Hole" was used for 225 years; one theory traces it to a Wampanoag word for "old man," another to an early English settler named Holmes. On February 21, 1871, the post office officially changed to Vineyard Haven, credited to Sarah Crocker. Tisbury is the town; Vineyard Haven is the village. Both names refer to the same place.
The harbor explains the town. Before the Cape Cod Canal opened in 1914, everything under sail between Boston and New York came through Vineyard Sound, some 27,000 vessels in 1870 alone, and Holmes Hole was the first or last safe anchorage on that road: a harbor of refuge with the chandlers, sail lofts, blacksmiths, bakeries and pilots to match. The canal took the traffic inside the Cape, the trucks and the railroad took the freight, and the working harbor of schooners became the harbor of ferries and yachts you see today. The boatyard and the schooners on the moorings are the part of that story that never quite ended.
Where to Stay in Vineyard Haven
Vineyard Haven’s lodging is small and personal: boutique inns rather than big hotels. The Mansion House Inn on Main Street stays open year-round, with a spa, gym and indoor pool (check rates). The Crocker House Inn sits in the lanes just off the harbor (check rates), and Charles and Charles is the bed-and-breakfast pick (check rates). For every option island-wide, with real prices by season, our complete Where to Stay guide covers 38 fact-checked properties.
At the other end of the budget, Harbor Landing at 15 Beach Street, under a sign that says established 1976, is a plain motel-style place with a shared kitchen and a harbor-view deck, and one of the few lower-priced beds within a few minutes' walk of the ferry. Our where to stay guide compares it with the rest of the town.
Vineyard Haven · 15 Beach StreetPhoto by MV Vacation
The Harbor Landing sign on Beach Street, a gull over the marsh and an established date of 1976.
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Getting Here and Around
The SSA ferry terminal (1 Water Street) is the only year-round port on Martha's Vineyard. Walk-on $11 one-way / $22 round-trip. Children 5–12 pay $5.75. Bikes $5.25 each way. Vehicles from $73.50. The 45-minute crossing from Woods Hole runs roughly 14 daily departures. The new Woods Hole terminal building opened in June 2026. The traditional vehicle standby line has been suspended since November 2024 (a limited Blue Line standby exists only for SSA preferred and excursion account holders), so all vehicles need advance reservations. Walk-on passengers are unaffected. The VTA bus hub is at the terminal; all routes connect here, currently fare-free. Bike rentals: Martha's Bike (4 Lagoon Pond Rd), All Star MV (Beach Rd), Vineyard Bike Rental (delivers island-wide).
For the complete ferry options and fares, see our Ferry Guide. Planning a one-day itinerary? Vineyard Haven is the natural starting point.
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Island tip of the dayFerryNo. 4 of 86New tip at midnight, island time
The Island Queen from Falmouth to Oak Bluffs is $20 one-way, $30 round-trip (35 min). Passengers and bikes only: no cars, and no dogs. Buy tickets at islandqueen.com; summer boats do fill.
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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.
Your insider guide to Martha's Vineyard: beaches, dining, events, and island living. We write down what we know about the island so your trip goes the way you hoped.
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.
New Woods Hole terminal, fare-free buses, new restaurants in Oak Bluffs and Vineyard Haven, a reopened lighthouse and more: everything that changed on the island in 2026.
MV packing list: tick protection (Lyme at 11x state avg), cash for Chappy Ferry, light jacket for July evenings, and what to rent not bring.
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The free island library · 2026
One short island letter, and all three guides to start
Beach reports, events worth a day, ferry heads-ups. Sent when there is something worth telling. The Beach Guide, The Vineyard in the Fall and Where to Stay arrive with your welcome email.