Below you will find my favorite spots that I make sure to visit every time I go to Martha's Vineyard. Whether you're planning your first trip to the island, or your old station wagon is covered with 20+ years of Lucy Vincent Beach passes, I'm sure you will enjoy them!
Disclaimer: My list is fairly "up-Island" focused, because that is the area I know best. So for you veteran Vineyarders, please comment and add your recommendations as well!
The Outermost Inn & Restaurant
Located on the western shore of Aquinnah, this acclaimend inn and restaurant features possibly the best view on the island. Ideal for special occassions and private parties overlooking the magnificent Gay Head Cliffs. For reservations and more information, visit their website here: http://www.outermostinn.com.
The Home Port Restaurant
This is one of the most popular restaurants on the island, located in the authentic fishing village of Menemsha. Every night of the week, visitors and locals gather for takeout on the porch to watch the sunset. Tables are first come, first serve, so get there early to stake out your spot. Reservations are also accepted in the indoor dining section of the restaurant. The menu includes freshly-caught island classics like whole boiled lobster and Menemsha swordfish. For a full menu and directions visit their website: http://www.homeportmv.com/index.php.
Beach Plum Inn
The Beach Plum restaurant was ranked as Best Restaurant in Martha's Vineyard, and in the Top Six in New England by Food and Wine. Guests at this small inn will enjoy amazing cooked-to-order breakfasts every morning on the beautiful patio overlooking Menemsha harbor. The inn has rooms in the main house, as well as private cottages which are ideal for a longer stay. Best of all, the inn also provides transportation to and from beautiful Lucy Vincent beach, which is only accessible to those staying in Chilmark. Visit the Beach Plum website here: http://www.beachpluminn.com/theinn.htm.
Flying Horses Carousel in Oak Bluffs
No trip to the Vineyard is complete without visiting the historic town of Oak Bluffs. In addition to the beautiful victorian houses, Oak Bluffs is home to the famous Flying Horses Carousel, a National Historic Landmark and the nation's oldest operating platform carousel, according to the Martha's Vineyard Preservation Trust. Children as well as adults will enjoy riding the carousel and trying to catch the brass rings, which will win you a free ride. After the carousel, head accross the street for some Mad Martha's ice cream! This homemade, island ice cream "chain" is also located in Vineyard Haven and Edgartown.
Moshup Beach in Aquinnah
Moshup Beach is one of the best public beaches on the island. Set agains Gay Head's beautiful cliffs, you will see hundreds of rock sculptures that visitors have built for everyone to enjoy. After the beach, head up the road for a casual lunch or dinner at the Aquinnah Restaurant. For a listing of all beaches in Martha's Vineyard visit here: http://www.mvol.com/beaches
Shopping in Edgartown and Vineyard Haven
If you find yourself with a rainy day, or just need a break from the beach, head to Edgartown or Vineyard Haven for shopping! Both are beautiful towns with a variety of stores where you can pick up island-made jewlery, chocolate, pottery and your Black Dog shirt. My favorite is Midnight Farm in Vineyard Haven, an Anthropologie-esq home and clothes store owned by Carly Simon.
Before you get on the ferry, check one of our books in the Places section of the library!
Photo's courtesy of Flickr users Jeffer 72, KariemAli, Juleann on mv, room714, Timothy Valentine, texturejunky, and Chris Devers.