Martha’s Vineyard Summer 2020

The summer season of 2020 is fast approaching Martha’s Vineyard. This season is facing some very different challenges but there are lots of reasons why 2020 could very well be a truly great summer. I’ve given this blog post a lot of thought and I have decided that the next few months will prove an opportunity for islanders, washashores, summer DINKs, and weekenders alike. Let’s have a look at what Martha’s Vineyard means even as I type this post…

Sunset Martha's Vineyard

Menemsha Sunsets with Friends and Take-Out

Martha’s Vineyard’s 2020 Menu

There’s no denying it—there have been a lot of changes and people are unsure about the future. What I can tell you, what I am happy to report, is that a lot of your favourite Martha’s Vineyard restaurants are already open for business! You can’t dine-in at the moment but you can get most of your favourite dishes take-out and frankly, I don’t see that as a problem. I have seen my friends’ posts of them eating sushi, lobster rolls, fries, and lots of other goodies from Nancy’s Restaurant! They collected their order and ate it on their boat in Oak bluffs Harbor! What could be better than that? I have had other friends picking up take-out from Rockfish and heading out as far as Menemsha Beach to watch the sunset! We all know what a spectacle a Menemsha sunset is. Adding one or two Rockfish flatbreads is a mind-blowing concept. It’s really hard to work up sympathy for people who have to suffer through these options.

Nancy’s Restaurant on Oak Bluffs Harbor

The last I heard, the following restaurants were open: Nancy’s, Linda Jean’s, Rockfish, Sharky’s, Giordano’s, Ben & Bill’s, Jimmy Sea’s, Lookout Tavern, Edgartown Seafood, Sweet Life Café, Offshore Ale, Port Hunter, Coop De Ville, Bettini, Life At Humphrey’s, Nat’s Nook, Chilmark Tavern, Alchemy, and Pizza Di Napoli. At the moment they are all open for take-out only. That’s a lot of delicious choice for one little island. Limited seating is on the horizon at the beginning of next month and I am cautiously optimistic.

Martha’s Vineyard’s 2020: The Outdoor Sport

Long before we had Best Of The Vineyard, Taste Of The Vineyard, Beach Road Weekend, or Agricultural Fair, Martha’s Vineyard was considered a world class vacation spot. Why? Because of what she was and what she still is today—a beautiful landscape trimmed with some of the best beaches the world has to offer. If Martha’s Vineyard has meant nothing to you in the past but Main Street Edgartown and Circuit Avenue Oak Bluffs, this is the perfect opportunity to see the rest of the island! You will wonder what took you so long. Once you have gone to your favourite restaurant and packed up some delicious meals-to-go, head out onto some of the island’s incredible hiking trails.

Menemsha Hills Martha's Vineyard

The Foot of Menemsha Hills Hiking Trail

It doesn’t matter what your athletic level is, Martha’s Vineyard has the trail for you. Gentle flatland strolls, boardwalk strolls, uphill hikes, and everything in between! Abel’s Hill, Menemsha Hills, Great Rock Bight, and Caroline Tuthill Preserve just to name a few. I highly recommend downloading the ‘Trails MV’ app to your phone. In it, you will find maps and listings of all of the island trails. You can check them all off as you’ve done them and try to complete them all! Exactly how many trails does it take to work off a take-out lobster roll? I’m not sure. Just get moving. By May 25th, all of the parks will be open so I believe Mytoi Gardens on Chappaquiddick and Polly Hill Arboretum will both be open. I strongly suggest spending some zen time in both of them.

Polly Hill Martha's Vineyard

Rhododendron in Polly Hill Arboretum

Shopping, at least in the beginning, will also be an outdoor sport but that could be fun too! Starting May 25th, retail stores are starting curtsied service. Have you ever been to Martha’s Vineyard’s Tivoli Day? It’s a great time. A giant sidewalk sale in Oak Bluffs. Well, I imagine that the season will start like a great big Tivoli Day celebration. Cool places like Slip77 on Circuit Avenue will be offering curb-side sales for their patrons. If you’re a shopper, a stroll down the main strip on a sunny day picking up some great island clothes will be just the ticket to help you detox from the past three months. It’s important to note that most island stores are available for on-line shopping as well.

Slip77 Martha's Vineyard

Slip77 sets the standard for playful cool island style.

Social Distancing Martha’s Vineyard Style

As we all know, social distancing is the way to beat this thing. Social distancing prevents spreading COVID-19. If you don’t catch it, the people who do have it recover, and the numbers dwindle. The more we social distance, the better. We can stay with the two, four, or six people we live with obviously bu other than that, it’s important to stay apart. If only there was a way to guarantee maintaining a safe distance from others around you. A way you could stay more than six feet, heck more than six metres, more than sixty metres away from the general population and have the best vacation experience of your life! Wait a minute… something is coming to me… How about a sail on Catboat Charters?

Catboat Charters Martha's Vineyard

Tigress: Martha’s Vineyard’s Flag Ship

Tigress is a ninety-two-year-old wooden catboat meticulously maintained by Captain Kurt Peterson. Captain Kurt has been a fixture in Edgartown Harbor for going on six years now. You may have even seen him driving the Chappy Ferry this past winter! If there’s an individual who has spent more time on the harbour this past couple of years, I’m not sure who it is. Captain Kurt and Tigress are ready to take people out for the best time you can possibly have social distancing. They have put some new regulations in place to make their guests’ sails the safest and most enjoyable part of their island stay. Captain Kurt has even taken to wearing a fun and friendly tiger face mask! Now, he really is the coolest cat on the harbour! I just have one question, I know he can still play the banjo with his tiger mask on, but can he sing through it? I hope so. Sailing with Catboat Charters is definitely something everyone should do on Martha’s Vineyard. Social distancing just gave us all the perfect excuse!

Catboat charters Martha's Vineyard

Captain Kurt Peterson complete with Tiger Mask!

Martha’s Vineyard

Times are a little scary right now. People like the status quo, they don’t like change and uncertainty. I am definitely one of those people. We need to accept the very real possibility that things might never be what they were, and that’s okay. Just because something is different doesn’t mean it’s bad. Life is change. Sands shift, waves roll in and out, nothing stays the same. Martha’s Vineyard has the reputation for being unchanged over all these centuries but that’s not true. It has changed consistently. This will change the island and the island will adapt. The hard-working people of Martha’s Vineyard will figure out a way to make the future work for them just as all of their ancestors have before them. Martha’s Vineyard is my favourite place in the world and she’s waiting to welcome us back. Stay safe, healthy, and happy everyone.


  1. Reading your blogs makes me feel that I’m there, your love for the island bleeds through your words..
    Thank you for the updates.

  2. Once again, great post filled with info from a fellow Vineyard Veteran…makes me feel a bit more optimistic about locking up my August plans to spend a week here…👍🏻

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