August 10, 2016 Kim Cox

Martha’s Vineyard – Off the Beaten Path

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How to Enjoy Martha’s Vineyard like a Local.

Each year, thousands of visitors flock to Martha’s Vineyard for the perfect summer vacation. Most of them read a guidebook and end up doing the same old things. Even seasoned visitors miss some of the best parts of the island simply because they don’t know about them. This guide gives you the information that doesn’t make it to the guidebooks and will help you enjoy the best of the Vineyard – like a local!


21 Things to do on Martha’s Vineyard that

 Martha's Vineyard

For more information about visiting Martha’s Vineyard, read my earlier post, The Best Guide to Martha’s Vineyard You Will Ever Read. 

1.  Eat Donuts from the Back Door.

Martha's vineyard

If you look in the phone book for Back Door Donuts,  (who’s got a phone book these days?) you won’t find a listing for it because it doesn’t exist. What does exist is Martha’s Vineyard Cafe and Bakery. After selling baked goods all day in the main store, they close up shop, then sell donuts from the back door. It’s a genius marketing idea! These are best donuts, apple fritters and cinnamon rolls on all of the island! Be prepared to wait. The line is long, but so worth it.

2. Jump off the Jaws bridge.

It’s a rite of passage. If you don’t have the guts to jump, it’s fun watching anyway.  The bridge is easy to find, just look for the crowd along State Beach.

3. Buy some unique goods at the Chilmark Flea Market.

The Chilmark Flea Market is held every Wednesday and Saturday during the summer months. It’s a great place to buy locally sourced, unusual and handmade items.

4. Buy fresh produce at Morning Glory Farm.

Martha's vineyard

Morning Glory is a working farm and “freshly picked” usually means picked just a few hours ago! They also sell pre-packaged meals and baked goods. Call ahead to see if they have monkey bars. You can thank me later.

5.  Eat pizza in the rocking chairs on the porch of Chilmark General Store.

You should drive up-island at least once during your trip, and when you do, don’t miss out on the best pizza on the island. Enjoy your slice in the rocking chairs on the front porch – it’s the best place to spot a celebrity!

6.  Enjoy Chilmark Chocolates.

For a sweet treat, (after your pizza) walk on over to Chilmark Chocolates. The delectable chocolates are lovingly made and the selection is great. Plan your trip ahead – it’s only open certain days.

7.  Swim at Ice House Pond.

Ice House Pond is a pristine swimming hole, created by a glacier and tucked away in the woods. You must be quiet while swimming there, since it is surrounded by homes and sound carries eerily well. There are only 6 parking spaces, so plan accordingly.

8.  Catch the Vineyard Haven Band on Sunday nights.


Throughout the summer months, the band plays patriotic and show tunes at the bandstand in Oak Bluffs or in Vineyard Haven. Children and adults alike dance and march to the tunes as they waft out to the ocean.

9.  Take a shower outdoors – but only if your rental has an outdoor shower attached!

Martha's vineyard

You haven’t enjoyed a shower until you’ve enjoyed an outdoor shower! Most island rentals them.

10.  Share a pizza and a smile.

Martha's vineyard

On Wednesday evening, go up to Chilmark for “community pizza” night at the Orange Peel Bakery. Bring a topping to share and $10 dollars. Create your own specialty pizza with the donated toppings and share it with other pizza lovers on picnic tables and blankets in the front yard.

11.  Eat lobster at the Net Result.

There’s no need to drive up island for lobster. You can get the same lobster, at half the price, at the Net Result. Pick it up at the window and join the other patrons at the picnic tables.

12.  Ward off vampires at Jimmy Seas.


If garlic is your thing, Jimmy Seas is your place. Family style pasta dishes packed with flavor are served up nightly.

13. Enjoy Shakespeare in the woods.

Tucked away off State Road, is a small amphitheater that is home to weekly productions of Shakespeare’s plays.   Feel free to bring along a bottle of wine – and some bug spray.

14.  Work out at the Y.

The Vineyard YMCA is a beautiful modern facility with state of the art equipment and classes.

15.   Enjoy the Vineyard Sound.

The acapella group, Vineyard Sound, performs at several venues around town. Check the newspaper to see where they will perform during your stay. They are really good.

16.  Visit the grave of John Belushi.

17.    Tour the Japanese Mytoi garden on Chappaquiddick.

18.  Take a cooking class.

Martha's vineyard

The Kitchen Porch offers “farm tour”  cooking classes.  You tour the farm, pick the produce, then cook a meal with it – all in one morning! This is as”farm to table” as you can get!

Martha's vineyard

19. Enjoy a lobster roll at a church fundraiser.

You can buy them in a restaurant, but they taste better on the church lawn.

20.     Take in an Improv theatre performance.

Check the paper when you arrive to get the schedule.

21.  Find the “Kennedy” bridge on Chappaquiddick.


Did I leave out anything?

But WAIT!  Before you go to Martha’s Vineyard, you’ll want to read my earlier post, The Best Guide to Martha’s Vineyard You Will Ever Read.

Martha's vineyard

Have a great vacation – and leave a lobster for me!

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