Top 10 Must Dos for Any First Time Visit to Martha’s Vineyard

Fall has arrived and now is the perfect time for those weekend trips to places that are too crowded in the summer.  The weather is still nice and the crowds have departed.  Just a hop skip and  jump from Boston and Providence, Martha’s Vineyard is the perfect weekend getaway to hold on to the last few days of summer, before the weather turns.  Here are your top 10 must dos for your first time visit the Martha’s Vineyard.

Aquinnah

A visit to the vineyard is not complete without checking out the cliffs of Aquinnah (formerly known as Gay Head).  With their gorgeous colors and rich Native American history, Aquinnah is a great place to spend the afternoon.  Spend some time walking the tops of the cliffs as well as the beaches below.  If you are lucky enough to be there when the Gay Head lighthouse is open, definitely check it out for additional coastline view.  Make sure to stop at the Orange Peel Bakery for some goodies on the drive up.

Top 10 Must Sees For Any First Time Visit to Martha's Vineyard: Aquinnah

Top 10 Must Sees For Any First Time Visit to Martha's Vineyard: Aquinnah

Menemsha

While you are “up island” visiting Aquinnah, head over to Menemsha for lunch.  This quaint fishing village is home to some of the islands best lobster rolls and amazing scenery that reminds you what this island is all about.  Whether you visit The Galley (our favorite) or Larsen’s Fish Market, the food is delicious in this tiny town.  Get there early before parking fills up.

Top 10 Must Dos for Any First Time Visit to Martha's Vineyard: Menemsha

The Beach

Most trips to Martha’s Vineyard are all about the beach, and there is a good reason, the beaches are gorgeous.  Pick your beach, grab your towel, picnic lunch and head out. For the best beaches on Martha’s Vineyard, check out here.

Top 10 Must Sees For Any First Time Visit to Martha's Vineyard: Beaches

Top 10 Must Sees For Any First Time Visit to Martha's Vineyard: Beaches

Gingerbread Cottages of Oak Bluffs

Originally built as a religious community, these colorful and beautifully decorated houses are a great place to spend an afternoon wandering.  Right next to downtown Oak Bluffs, each house in the campground has it’s own look and feel.  Don’t miss the community sing every Wednesday night at 8PM or illumination night (an annual event in August, when the houses are lit up with paper lanterns).

Top 10 Must Sees For Any First Time Visit to Martha's Vineyard: Gingerbread Houses

Ride the Flying Horses

While you are in Oak Bluffs admiring the gingerbread houses, make sure to stop on over at the Flying Horses, the oldest operating carousel in the United States.  This rainy day activity is a kid favorite.  Attempt to get the brass ring for a free ride and hit up the old school arcade games afterwards.

Eat a Lobster Roll and Ice Cream

It’s vacation, the diet is out the window. Lobster rolls and ice cream are a religion on Martha’s Vineyard.  You can get both everywhere and there are so many good options, try as many as you can.

Top 10 Must Dos for Any First Time Visit to Martha's Vineyard

Go for a Ride

With a plethora of bike paths, you can get almost everywhere on bike, and given the traffic, you can often get there faster on bike, plus this is the best way to see the cute houses, stores, and gorgeous scenery.

Top 10 Must Dos for Any First Time Visit to Martha's Vineyard

Visit Remote Chappaquiddick

Famous for the Kennedy incident in the late ’60s, Chappaquiddick is where people go to escape the crowds.  There is not a lot there, no really only one general store, but with gorgeous white sand beaches and amazing wildlife, Chappauiddick is a great place to spend the day.  Pack up the car, take the tiny ferry (3 cars only) and head over for a day of relaxation.  Visit the picturesque Mytoi for some serious contemplation or just relax and do nothing on the beach.

Top 10 Must Sees For Any First Time Visit to Martha's Vineyard: Chappaquiddick

Shopping

There is great shopping on Martha’s Vineyard.  Each town has it’s own feeling and vibe and that includes the shopping.  Some of the best women’s fashion shopping is in Edgartown, the best shopping for T-shirts and souvenirs is in Oak Bluffs, and Vineyard Haven has the best home goods shopping.  Also check out the artisan fairs and farmers markets for one-of-a-kind finds.

Top 10 Must Sees For Any First Time Visit to Martha's Vineyard: Shopping

Visit the Lighthouses

Martha’s Vineyard has five lighthouses: West Chop, East Chop, Edgartown, Gay Head, and Cape Pogue, each one has it’s own unique charm.  Take an afternoon bring your beach stuff and climb those stairs for great views and a little bit of island history.

Top 10 Must Sees For Any First Time Visit to Martha's Vineyard: Lighthouses

There is so much to do on Martha’s Vineyard, but here are my top 10 essentials for any first time visitor to get a flavor of the island and all it has to offer.  Happy exploring and let me know what your favorite activities are.

Top 10 Must Dos for Any First Time Visit to Martha's Vineyard: Menemsha

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