As SF transplants, we love the Hamptons but would love to check out MV. What are the classic spots, the scene for dinner, the bars not to miss. We are looking for the classic/old school vibe -- not divey/collegey spots!
Edgartown is a classic New England whaling town: picket fences, widow's walks, brick sidewalks and great boutique shopping. Atlantic has great water views for dinner with an extensive menu and good bar vibe. They often have live music at night. Bad Martha Farmer’s Brewery is new for 2014 and is located just outside of town. Atria requires reservations and has an excellent brick cellar burger bar in addition to the upstairs menu. The Port Hunter offers an excellent raw bar and a fun bar scene, also with live music often.
Oak Bluffs is better known for the Flying Horses Carousel, the oldest carousel in the country, and is often busy with day-trippers. President Obama has frequented Nancy's Restaurant for the snack shack on the lower level. Nancy's also has great harbor views and people watching, along with two floors of outdoor bar area. Nancy's Upstairs offers sit down lunch and dinner. 20ByNine is new to the scene in 2014, with small batch bourbon and craft beers as well as small plates. Lookout Tavern is across from the Steamship boat dock and new fishing pier, sushi and pub type fare and porch seating. Martha's Vineyard Chowder Company has a nice bar and if you're lucky, there may be a concert at Dreamland which is above the Chowder Co.
Renting bikes to see the island is very doable as there are many wide bike paths and down island (Edgartown, Oak Bluffs, Vineyard Haven) are mainly flat. Many people like to jump off the "Jaws Bridge" which is on Beach Road at Joseph Sylvia State Beach (Oak Bluffs).
West Tisbury and Chilmark have beautiful rolling hills and farms as well as amazing beaches which are private to town residents or renters. State Road Restaurant in West Tisbury serves excellent food in a quaint farmhouse setting, reservations are a must. Sunday breakfast is awesome too!
Sunsets in Menemsha are fun. Menemsha is a fishing village in Chilmark. Menemsha Galley has soft serve ice cream, Larsen's Fish Market, The Bite, Menemsha Fish Market, and The Homeport side door all offer food to go to sit on the beach and watch the sunset. Since the town is dry, it is BYOB.
Until recently, Vineyard Haven, West Tisbury, Chilmark, and Aquinnah (Gay Head) were dry. Now, Vineyard Haven and West Tisbury have limited alcohol that is served in some of their restaurants, but no bars.
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If you are looking for classic/old school then I would recommend spending time in Edgartown. It is very charming and picturesque. The Harbor View Hotel & Resort is a great hotel with a very nice bar. A must visit is the Atlantic Restaurant...great old school bar and instead of peanuts or chips, they have cups of bacon as their bar snack. Seafood Shanty is a good spot for lunch...eat upstairs so you have a view of the harbor. Chesca's is a good spot for dinner and Kelley House is a good pub with a very New England atmosphere. For a unique dinner experience, head to Menemsha which is a sleepy fishing village (they filmed much of Jaws here) and buy a lobster dinner to go from Larsen's and have a picnic on the beach. Bring your own alcohol, towels and chairs. They will provide all of the food. Oak Bluffs and Vineyard Haven are great towns as well. Lots of fun bars and restaurants.
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