I go to Martha's Vineyard a couple of times a year.  We have our annual morning show broadcast from the Nobnocket Boutique Inn, but we also always try to go to the Vineyard during the offseason...sometimes in the dead of winter.  We've spent a good amount of time driving the main streets and back roads of the Vineyard, so I figured I'd share a list of some of my favorite things to do while we're there.

 

  • Giordano's Italian Restaurant

    Oak Bluffs

    The truth of the matter is, I was initially introduced to Giordano's because I went to Syracuse University with "Gio".  We lived on the same floor in Flint Hall our freshman year.  Gio's family has owned Giordano's for generations.  They are an institution on the Vineyard.  I haven't been able to wrestle their sauce recipe away from them, yet...but you should make sure to enjoy it on your next visit.  I'm sure it's no surprise that Giordano's serves Italian food, considering the last name.  I'd recommend the chicken parm and the pizza.  The salads are also solid.

  • Mad Martha's Ice Cream

    Vineyard Haven

    Open 7 days a week (in season), Mad Martha's is something you have to do when visiting Martha's Vineyard.  Several US Presidents have been photographed enjoying Mad Martha's ice cream.   You can order a usual, but delicious, vanilla or flavors a little more on the wild side like "Lotsa Dough" or "Snickers".  The one drawback, Mad Martha's is closed during the off-season (like all of the other island ice cream spots.

  • Ryan's Family Amusement: Oak Bluffs Game Room

    Oak Bluffs

    Like so many things on Martha's Vineyard, it's like stepping into a time machine when you step into the arcade in Oak Bluffs.  My kids love Ryan's Family Amusement in Oak Bluffs.  The video games range from throwbacks from the 80's (like Ms. Pac Man) to current.

    #winning

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  • The Boneyard Surf and Skate Shop

    Edgartown

    Whether you surf or not, The Boneyard on Main Street in Edgartown is worth the trip. Whether you're looking for something to wear to the beach or maybe a boogie board to keep the kids occupied, The Boneyard has all kinds of cool options. In fact, the entire strip on Main Street in Edgartown is a fun place to shop.  A decent number of the stores are open off season.

  • Bike Paths

    Vineyard Haven

    Whether you ride bikes for fitness, challenge, or leisure, the bike paths on the Vineyard are some of the best. You have some short but sweet paths that even the most seasoned bicyclist will enjoy.

    Google Earth
  • Flying Horses Carousel

    Oak Bluffs

    Considered by the US Government to be a national landmark, the Flying Horses Carousel is the longest standing platform carousel in the nation. Since its construction in the late 1800s, this carousel is still high flying fun the kids can enjoy.  See if you can grab the "special" coin and win a free ride!

    3 dollars per ride

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  • Gayhead Lighthouse

    Aquinnah

    If you are looking for pure, unadulterated nature on the Vineyard...there are a lot of locations to choose from, but there's really nothing quite as unique and picturesque as the Aquinnah Cliffs overlook.  An interesting fact:  The Gay Head Lighthouse, which overlooks the cliffs, was moved back 129 feet three years ago to protect it from the erosion.  Without the move, the lighthouse would have fallen down into the ocean.

    TSM
  • Newes Restaurant and Pub

    Edgartown

    If you are looking for a cozy, colonial dinner by a roaring fire...you need to head to the Newes from America Pub.  You can feel the history dripping from the exposed wooden beams and rickety floor.  The menu is made up of pub favorites and nightly specials.  It's located in the basement of The Kelley House, the oldest Inn on Martha’s Vineyard.

  • Gingerbread Houses

    Oak Bluffs

    Oak Bluffs is famous for their gingerbread-style houses.  The colorful cottage village in the heart of Oak Bluffs. You'll feel like your walking in a Candy Land world as you stroll past.  As former Methodist camp meeting houses in the late 1800s, all 318 of these well-preserved gems are a must-see when visiting the island.

  • Vineyard Vines

    Edgartown

    Vineyard Vines has grown from a one-off store on the Vineyard to a national brand.  The brand, which was created by two local brothers, is now big enough to be able to afford signage above the 3rd baseline in Fenway Park.  One Vineyard Vines sweatshirt is roughly the cost of a week's vacation on the Vineyard.  That might be an exaggeration.  A slight exaggeration.