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Martha’s Vineyard Guide: My Favorite Places

August 25, 2017

Martha’s Vineyard is very special to me. I have been visiting the Island every summer since I was 13, and Will and I met and married there.   We spent a week in August visiting family and I wanted to share some of our favorite spots, old and new!    There are three main towns on Island, Vineyard Haven, Oakbluffs and Edgartown as well as “up island” which is much more rural and spread out but where some of the most beautiful beaches are.   Our family home is outside of Vineyard Haven so that’s where we spend most of our time but I also love Edgartown and we go up island most days.   It is surprisingly spread out, and in the August traffic, it can take an hour or so to get between towns.  My favorite time of year to visit is the fall.  September and October have the most beautiful weather with less crowds and the sea is still warm enough to swim in. I created this Martha’s Vineyard guide so you can visit some of my favorite spots!

Martha's Vineyard Guide - New England style home on Martha's VineyardMartha's Vineyard Guide - Boats in the harbor on Martha's Vineyard

In my opinion, Edgartown is the most picturesque with traditional New England white wash or shingle houses, rows of lavender and periwinkle hydrangeas and lots of American Flags out front (definitely very easy to snap pictures in).    It sits right on the harbor and it’s lovely to watch all the boats going by (you can charter a sail boat out of here).   It’s worth strolling both in town and through the residential streets for the beautiful houses.   There is also a lighthouse with fantastic views of the harbor and a hotel across the street with a porch for sipping a cocktail.    While I spend less time in Edgartown in August (just due to logistics), it is one of my favorites to visit and I wouldn’t miss the shops along the harbor. I love the new shop Edgar which sells great summer clothes, from kaftans to ripped jean shorts to cute bikinis.  I bought two swim suit coverups here for our trip to St. Barth’s.  I also love getting lost at Portobello Road, a very fun and eclectic book store — a great place to get lost.  There is an ice cream store called Scoops and the best lobster roll in town is on the corner — the shoestring fries are fantastic!  There is a restaurant which I haven’t tried yet but which I am dying to go to (it has been booked for private events on the nights we could have visited), it is called The Covington and it’s farm to table.   I have not stayed in Edgartown but the Hob Knob looks divine and has great reviews!   I should also note that Will and I live out of Morning Glory farm which is just outside of Edgartown.  We get all of our produce there but particularly love their prepared salads, quiches, pies, crumbles and fresh bread.  The chocolate chip cookie is the best I have ever had.

Martha's Vineyard Guide - Blue and pink hydrangeas Martha's Vineyard Guide - New England style home surrounded by hydrangeas Martha's Vineyard Guide - Boats in the harbor on Martha's VineyardMartha's Vineyard Guide - Pink and orange flowers in Martha's Vineyard Martha's Vineyard Guide - Lobster roll, fries, and a beer Martha's Vineyard Guide - Inside a cozy bookstore on Martha's VineyardMartha's Vineyard Guide - Pink and orange flowers on Martha's vineyard Martha's Vineyard Guide Martha's Vineyard Guide - New England style home surrounded by hydrangeas

If you are spending the day in Edgartown, it’s worth zipping up to Menempsha for sunset.  Menempsha is an old fishing village (and actually probably has the best lobster rollls on Island — try Larsen’s!) which is very picturesque and well placed for a sunset views.   It has lots of little dives where you can get wonderful fresh seafood and great things like fried clams.  For a more formal sit down, there’s the Homeport or just before you get to Menempsha there’s a great restaurant called the Beach Plum Inn.  Memempsha is a dry town so BYOB!!! It is totally crushing to sit down to dinner ready for a glass of wine only to realize you were supposed to bring it yourself and the closest liquor stores are twenty minutes away.

Martha's Vineyard Guide - the outside of a dive restaurant called The Bite on Martha's VineyardMartha's Vineyard Guide

I love being up island.   Middle road is my favorite to drive down, it is lined with stone walls and fields of grazing cows and sheep and occasional views of the sea breaking beyond — so beautiful.  Allen Farm is where we photograph most of our weddings and is stunning.  The event side isn’t open the the public but you can peek over the gate and across the street there is a lovely little shop.   My favorite beaches, and the most wild and wavy, are up here en route to Aquinnah which sits at the top of the Island and also offers fantastic sunset views and is worth walking up to.   I often stop at the Chilmark store for a slice of pizza (the vegetable of the day is my favorite) and some water for the beach.   And, in the off season, Chilmark chocolates is great fun and makes for good presents to take home.

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We just discovered Grey Barn this year which is an amazing property.  There is a farm stand which sells meat raised on the farm, as well as delicious cheeses (which have made it all the way to Brooklyn), vegetables and raw milk all packaged with such chic branding.  The property itself is like something out of a modern fairy tale, the gardens are so well designed and we loved looking at all the baby animals (like ducklings) with the baby too.

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Last but not least in our Martha’s Vineyard guide is closest to home, Vineyard Haven.   We live out of Blissed Out, the local smoothie shop (I love the strawberry patch smoothie with added protein which is probably a smoothie for children but it is delicious!) and Mocha Motts for coffee.   Also not to be missed is Bunch of Grapes (bookstore), the Black Dog (chocolate bomb is a great dessert), the Net Result for fresh seafood and sushi, Brickyard (eclectic homewares), the bike rental store on 5 corners, the Larter for local meats and sandwiches, Gannon and Benjamin (incredible wooden sailing boat makers and you can charter them), and sunsets at West Chop.  Perhaps my favorite discovery of the summer though was the new store Magnetic North which sold everything from beautiful watercolors to kaftans to cashmere.  I absolutely love love love this shop and the cafe behind and am drawing major inspiration from the owner Maggie’s incredible taste!  Pictured below is the Larter and then Magnetic North followed by scenes from the harbor and a G&B Sailing boat.
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Martha’s Vineyard style celebrates natural beauty and is casual cool and relaxed if not a bit etherial.   Here is a peek at my MV uniform which includes Barbour, Hunter boots, cozy sweaters and feminine dresses. Hope you enjoyed this Martha’s Vineyard guide!


  • Reply Taylor August 25, 2017 at 12:29 pm

    Martha’s Vineyard looks so beautiful, I would love to take a trip next summer! I am definitely saving this post for future use!

    Taylor |

  • Reply Babylyn Gonzales July 23, 2018 at 10:40 pm

    Always dream of visiting this place since the Kennedys time….

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