The Black Dog is more than just a t-shirt, it's also a great restaurant on Vineyard Haven Harbor.
Visitors | Getting Here | Weekend | 7 Days | Kids | Facts
Martha's Vineyard packs a lot into its 87 square miles - from the unique charms of its three main towns - to its world renowned beaches - to the beauty and serenity of the sparsely populated up-island areas. If you've got two days, you can easily explore the entire island.
Day 1: Exploring the Major Towns of Martha's Vineyard
If you arrive in Vineyard Haven, the main port-of-call for the island, you can get into the Vineyard state of mind by having breakfast or lunch at the world famous Black Dog Tavern where you'll have a great view of the VH harbor from the rustic dining room. Vineyard Haven is known for its eclectic mix of shops from Carly Simon's Midnight Farm - a boutique and funky home goods store - to the country classics of Bramhall and Dunn. You might want to come back to VH for a little shopping therapy later on but for now...
Head over to Oak Bluffs, a ten-minute drive from Vineyard Haven along a lovely harbor view road. The most colorful town (both literally and figuratively,) Oak Bluffs is home to the celebrated Gingerbread Cottages. A stroll through the Oak Bluffs Campground is a journey into a fantasy world of intricately carved miniature houses in candy-colored pastels. Oak Bluffs also has many other Victorian era homes scattered throughout its small downtown area and the famous Flying Horses - the oldest operating platform carousel in the US.
The next stop on your Island tour is Edgartown, and you get there via State Beach - a two-mile stretch of calm waters and smooth shores which is popular with families. If you're looking for a little surf, continue on to Edgartown and check out the waves of South Beach, probably the most popular destination for younger beachgoers.
Edgartown proper is a picturesque whaling town. The colonial homes and historic buildings are all painted white, and picket fences and manicured flower gardens are de rigeur. Many charming B&Bs line the town's old-fashioned Main Street. Edgartown is also known for upscale shops and fine dining establishments.
Stop for a takeout lunch at the Quarterdeck where you'll find the best fried clams on island. Enjoy your snack on the upper deck of the Edgartown Wharf where you'll have a great view of the Edgartown Harbor and Chappaquiddick while watching the On Time ferry make its two-minute trip back and forth from tiny Chappy.
Edgartown and Oak Bluffs are the only two towns where liquor is sold on island. The bars of Edgartown range from fun and local to the classic elegance of the Harbor View Hotel & Resort's bar and Atria's Brick Cellar Bar.
If you’re staying in OB, you can head back to the Offshore Ale House where you'll find handcrafted beers and live music offered up in a loft-like, nautically themed setting. OB after dark boasts many sophisticated and casual dining and drinking establishments, while one of the most popular evening activities on Circuit Ave. is window shopping while enjoying a cone from one of six homemade ice cream shops.
Day 2: A Tour of Up-Island
Starting in Vineyard Haven, State Road climbs all the way up to the famous cliffs of Aquinnah - passing through lovely countryside reminiscent of Ireland, and the quaint New England towns of West Tisbury and Chilmark. Glimpses of the spectacular Chilmark and Aquinnah beaches are visible beyond green pastures dotted with sheep.
As you depart Vineyard Haven heading south (paradoxically) to up-island, you will pass a number of small interesting shops, restaurants and art galleries that continue - though become less frequent the higher you get. You'll probably want to grab something to eat along the way. Try the Scottish Bakehouse for prepared foods and baked goods with a healthy bent, or grab a lobster roll from Garcia's Deli (behind Alley's General Store) or wait until you get to Chilmark for a slice of pizza from the Chilmark Store. The porches of both shops are popular up-island hangouts and good spots to catch the gossip while you eat.
Along with a number of art galleries, two great stops to browse for handmade Vineyard souvenirs are Chilmark Pottery (actually in West Tisbury) and the Vineyard Glassworks in Chilmark. Both feature demonstrations of their respective crafts and beautiful high quality giftware.
A slight detour at Beetlebung Corner will provide you with a worthwhile side visit to the fishing town of Menemsha. In the summer months, Menemsha is THE spot for watching the sunset - either from the public beach where picnickers gather early (parking is limited) or from the dockside restaurant The Home Port, which features lots of standard seafood dishes and a window-lined dining room perfect for the view.
NOTE: You will find almost nothing open in the town of Chilmark (which includes Menemsha) or Aquinnah after Columbus Day so come prepared in the off-season.
At the very end of the island is a natural wonder that attracts visitors from all over the world - the clay cliffs of Aquinnah. From the roadside parking, a short walk up the hill past souvenir shops and snack bars leads to the lookout with a panoramic view of the Gay Head lighthouse, the cliffs and the Atlantic Ocean with the Elizabeth Islands and Nomans Land visible in the distance. This breathtaking view is reason enough to justify the drive. As you walk back down browse the shops for wampum and other Native American crafts offered at the Wampanoag-owned gift shops.
The beaches of up-island are mostly private, but as well as the Menemsha Beach, public access is provided at Lobsterville Beach in Aquinnah or the far more spectacular Moshup Beach at the bottom of the cliffs.
If you save the Menemsha detour for the trip back down island you can stay on North Road which is a very scenic route whose highlights include the picture perfect Captain Flanders House, a renovated 18th century whaling captain's house set on 60 acres of farmland complete with picturesque pond and two steers.
As North meets up with State Road and you pass Alley's on your left, you'll see a unique art gallery with outdoor sculptures prominently on display. Stop in at the popular Field Gallery to see work by some of the most talented artists from the Vineyard and stroll through the field amongst the frolicking figures created by owner Tom Maley.
Just below the Field Gallery is a fork, which gives you the option of heading east to Edgartown or Oak Bluffs or straight back to Vineyard Haven. Remember, if you're thirsty for more than a lemonade after all this sightseeing, Edgartown and OB are the only non-dry towns on this misleadingly named Vineyard. Cheers!
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