Local’s Guide: Vineyard Haven

Homes HoleOriginally named Homes Hole in the eighteenth century, Vineyard Haven is the access point to and from the ‘mainland’. The  Steamship Authority runs in and out of Vineyard Haven on a year round basis, and it’s home to roughly 2,000 year round residents. Here you’ll find quaint little boutiques, restaurants and galleries lining Main Street while wooden boats lazily swaying on their moorings basking in the summer sun in the harbor.

Vineyard Haven is home to the world famous Black Dog company. What originally started as a small Tavern for locals to gather for a decent hot meal on a cold dreary night, has grown to include an internationally known clothing line, cafes, bakeries, a wharf, and last but certainly not least, the Black Dog Tall Ships. The two large Schooners offer one of a kind experiences ranging from sunset sails to kids camps.

blackdogtavern

Vineyard Haven is also home to The Art Cliff, a small dinner with seating for about fifty that serves breakfast and lunch. The food here is well worth the wait for a table; even in the dead of winter locals are sitting outside waiting for a table. Another amazing bonus? During the summer months The Art Cliff has a food truck that they open in their parking lot between the hours of five PM to two AM for those who may need a late night snack. We recommend you try the garlic truffle fries. While they are available during lunch hours, the fries are so much better from the truck. They add more garlic and truffle oil to them as well as other herbs that just push it over the top. If you’re not in the mood for fries, then go for the double chocolate doughnut holes. Freshly made and dipped in warm frosting, these guys will satisfy even the strongest sweet tooth.

 Art Cliff Food Truck Elixabeth Cecil

On Fridays during the summer Grace Church is home to incredible Lobster Rolls that are so full of lobster you start to wonder if there’s even bread holding it all in. Just a short walk down Main Street and a on to Woodlawn Ave and you’re there!

Grace Church Matthew Weinstein NY Times

Once a year Vineyard Haven is hosts the Tisbury Street Fair. Main Street shuts down to traffic and booths line the streets with live music is played and great events for the kids to enjoy.

Tisbury-Street-Fair

 

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