Martha's Vineyard Winter
Flickr/Mass Travel (CC BY-ND 2.0)

As the saying goes: “Summer people, some are not!” While Martha’s Vineyard is loved by many as a summer destination, we feel that a Martha’s Vineyard’s winter is an underappreciated gem. In the colder months, explore quiet lighthouses tucked into the white snow or walk into your favorite restaurants without a wait. Embrace the chill and discover the hidden delights of a Martha’s Vineyard winter.


Flip Over Fantastic Food Festivals

While there’s plenty of tranquility in the winter, we’ll let you in on an island secret: sometimes the best way to get through the colder months is a good old fashion party. Of course, it doesn’t hurt that our favorite zany, winter festivals also happen to be food themed. Warm up from the February cold by eating mountainous amounts of chili at the Big Chili Contest. Boogie to the mariachi band that performs all day and feel justified in your eat-a-thon by helping to choose the festival winner. If the thought of eating chili all day isn’t enough to give you heart burn, you may just have the stomach for Wingfest at Shaky’s Cantina. Bring wet wipes and an empty stomach because Martha’s Vineyard winter is ready to deliver some seriously good eats.


Sledding Martha's Vineyard Winter
Flickr/N. Friedler (CC BY ND 2.0)

Play in the Snow

Fun in the sun is not just for summer anymore. The island is teeming with outdoor spots that are all the more gorgeous in the snow. Take a stroll on any of the Vineyard’s beaches, and build a snowman by the water . If you remember to pack your skates, you can glide around the peaceful Jernegan Pond, Sheriff’s Pond, or John Butler’s Mud Hole in Edgartown. Our favorite outdoor activity? Embrace Martha’s Vineyard winter’s reputation for blustery weather by going snowkiting. Just grab your skis, a kite, and some good old fashion grit, and you’ll be off sailing.


Eat to Your Heart’s Content

While it’s true that some restaurants are closed during the off-season, many exciting and delectable spots remain open all winter long.  Take a bite out of the modern American delights at State Road, which, coincidentally, happens to be one of our owner’s favorite restaurants.  For a meal with large portions and no pretensions, we recommend the Wharf Pub where you can order one of our favorite cold weather treats on the island, chowder fries (yes, that’s chowder with fries on top). On date night, head to the Alchemy with its fresh seafood and mouth-watering entrees like their half-chicken (not to mention, their hand-crafted cocktails). The only downside? You’re probably going to leave the island a few pounds heavier than when you came.


Martha's Vineyard Film Festival
Photo: MVFF

Join in on the Arts

No matter what time of year it is, art on the island never sleeps. Many of the island’s most vibrant galleries (including the Eisenhauer Gallery in the Square) stay open throughout the winter. Escape the cold winds by taking in some local culture. If your love of art leans more towards learning than appreciation, Featherstone Center for the Arts offers art classes of all types throughout the Martha’s Vineyard winter.


By far, our favorite event of the season (yes, even behind ChiliFest!) is the Martha’s Vineyard Film Festival in March. Sit back and grab your popcorn for a wide selection of films and have the opportunity to speak with their directors and creators. Plus, all moviegoers get food, live music, and guided meditations. With its quiet serenity, Martha’s Vineyard in the winter is the ideal time to get a little artsy.


The Peace and Quiet of a Martha’s Vineyard Winter

As much as we relish the lively hum that rings over the island in the summer months, the off-season is a time of relaxation and secret pleasures. Whether you’re strolling through the streets of Edgartown or off searching for the perfect sledding hill with friends, you’ll feel like you have the island all to yourself. It’s just you, snow, and sea as far as the eye can see. Take a page out of winter’s playbook and settle down for the season in the luxury suites at Vineyard Square.

Where to Get the Best Pizza on Martha’s Vineyard Near Edgartown
Explore Memorable Things to Do & See in West Tisbury
Spend a Day at the Manuel F. Correllus State Forest
See the Next Big Thing at a Martha’s Vineyard Film Festival
A Guide on How to Get to Martha’s Vineyard
A Look at the History of Our Edgartown Hotel
Celebrate the Season | A Guide to Christmas in Edgartown
Where to Get the Best Lunch in Edgartown

Winter Stare by Vonschnauzer-resized-600

People in the tourism industry refer to times of year in a different sort way than ordinary folk, especially here on Marthas Vineyard. Where you might say ‘summer’, we say ‘peak’ season. You may call them ‘spring’ or ‘fall’ but to us they are just ‘shoulder season’. These refer to our level of volume in the hotel, specifically and island-wide, in general.

After ten years in the business and six at the Colonial Inn, and having given it some thought, I personally have to break my year down differently. Spring is the ‘Anticipation’ season. After being closed for several months, I go a little stir crazy and it feels like it will be forever before we open up again and have guests to serve. (It is almost as bad as the furniture in the animated Beauty & the Beast, except I don’t sing as much as they do. It’s the ‘ennui’.) Summer shall hereby be known as ‘Madness’ season, simply due to the need to run madly about the property and the inability to form coherent thoughts. That’s how busy it feels some days. The fall, I call ‘Reprieve Season’. It is a time where the flow of guests begins to taper off slowly. While it would nice to be a little busier than we are, that is how it works at a beach-resort destination. It just naturally quiets, leading right into the final season: ‘Nostalgia season’ can strike at any time, but usually happens when our guest level drops below the number of employees we still have on hand. We usually have a ‘whoa…when did THIS happen’ moment in which we tell our staff they have some extra time off…um…Yay? That’s when I start thinking over the year and looking back and remembering some of our long-time repeat guests:

  • Brian and Lisa who come twice a year, when it’s quiet, whether they need a getaway or not!
  • Paul & Company who come for the MS Bike Tour fundraising ride in late April or early May. I have learned a lot about what makes wheel-chair accessible rooms easier to use with their patient help. (Several other wheel-chair bound guests have thanked me for those improvements to our rooms.)
  • Michael, Stacey and the boys (actual kids or photo shoot crew) who almost achieved ‘Permanent Resident’ status over the years, before they bought a place on Chappy! You know we are here for you when the power goes out over there!
  • Kevin & John visit regularly, even as busy as they must be. (I think Kevin is the only Town Mayor we have ever had in-house…)
  • Janet and Helen – together with Joanne and Evelyn form our own little book club as they exchange titles.
  • Kim & Marc and Christine & Joseph and their clans! A two-family long-weekend getaway, they have been as regular as clockwork. (They rented houses one year to accommodate their whole party…but secretly…I think they missed us too much to stay away.) How is it possible for kids to grow so much so fast?
  • Barry S. and his merry band from Maine- From reluctant bus drivers to allergic reactions…we have been through some fun bus tours!
  • Kris, Mike and the In-line skate group keep us busy and leave us their quiche from time to time!
  • Meg should bring her Adventurers back to see us, but since she still comes by just to pop in and give us updates on Little Man, Chase…we won’t nag!
  • Alan and Stephanie who 1st visited on their honeymoon and now come back with their boys, despite having a legendary air-conditioning problem on their 1st visit!

There are so many more…people we have grown to love over the years, kids we have had the privilege to watch grow into young ladies and gentlemen. We miss you when you’re gone and look forward to seeing you again soon!

So now that you know we miss you, what do you miss most about the Vineyard when you’re gone?

Photo by VonSchnauzer


Where to Get the Best Pizza on Martha’s Vineyard Near Edgartown
Explore Memorable Things to Do & See in West Tisbury
Spend a Day at the Manuel F. Correllus State Forest
See the Next Big Thing at a Martha’s Vineyard Film Festival
A Guide on How to Get to Martha’s Vineyard
A Look at the History of Our Edgartown Hotel
Celebrate the Season | A Guide to Christmas in Edgartown
Where to Get the Best Lunch in Edgartown