Vineyard Haven Main Street , Martha's Vineyard

Vineyard Haven's Main Street is the year-round commercial hub of Martha's Vineyard, and it feels different from Edgartown or Oak Bluffs. Where Edgartown feels upscale and polished with whaling captain mansions, and Oak Bluffs' Circuit Avenue is built around the summer crowd and the nightlife, Vineyard Haven is a working town with an artsy, local sensibility. Many businesses stay open year-round.

Filmed June 2021The island moves on: shops, signs and prices may differ from what you see here. The text of this guide was checked September 2026.

Shopping on Main Street

• Bunch of Grapes Bookstore (23 Main St): Independent bookstore since 1964, over 60 years on the island. Fiction, nonfiction, local authors, children's section, and frequent author events.
• Brickman's (8 Main St): Established since 1913. Clothing, footwear, sporting goods, and toys.
• C.B. Stark Jewelers (53A Main St): MV charms, pendants, custom jewelry for over 40 years.
• The Green Room (71 Main St): Menswear for 30+ years; sportswear, shoes, surf gear.
• Rainy Day (66 Main St): Home goods, island-made products, MV-themed items.
• LeRoux at Home: Three floors of kitchen goods and tableware. Companion shop LeRoux Gourmet across the street.

Restaurants and Cafés

• Toccopuro and Co. (15 Main St): The island coffee chain bought the longtime Mocha Mott's building after that cafe closed in January 2026 and was open there by September 2026, from 6 am, with coffee, smoothies, bubble tea, breakfast and lunch; Mocha Mott's continues in Oak Bluffs.
• Delicious MV (22 Main St): French pastries, coffee, ice cream.
• Waterside Market (82 Main St): Year-round market and café with organic/locally sourced food.
• The Attic: Elevated tavern above Waterside Market with cocktails, steak, and seafood.
• Mad Martha's Ice Cream (48 Main St): Locally made ice cream since 1971.
• Black Dog Tavern (20 Beach St Extension): Founded in 1971 by Captain Robert Douglas. Year-round with harbor views. Not on Main Street but a short walk toward the ferry.

First Friday Events

Free community outdoor arts and culture events held the first Friday of each month, June through October, plus December. Features an art market with local makers on Main Street (10 AM–2 PM), live music, food trucks, silent disco, and bonfires at Owen Park (5 PM). The whole town turns out for it.

Dry Town History

Tisbury went dry in 1834, almost a century before Prohibition. Restaurants were BYOB for decades. In 2008, a ballot vote on allowing beer/wine tied 690–690 and did not pass. Voters gradually approved alcohol: beer/wine at restaurants in 2009–2010, full liquor in 2017, and service without requiring food in 2022. Current status: restaurants serve beer, wine, and full liquor. Chilmark remains the last dry town on Martha's Vineyard.

Getting Here

Vineyard Haven is Martha's Vineyard's year-round ferry port. 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.