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Martha’s Vineyard in late summer

Late Summer on Martha’s Vineyard is “A Season All Its Own”.  

Having just spent 4 days on the Vineyard, the crowds have lessened and political parties have gone back to Washington.  Sailing into Menemsha, Vineyard Haven, Edgartown or Oak Bluffs harbors, you will be assured a totally unique experience in each port town. 

Suggested Itineraries for the yachting set are here.

Please note: This is an original publication of the Martha’s Vineyard Chamber of Commerce.

People often mistakenly think that “the season” on Martha’s Vineyard ends Labor Day, but boy is that wrong! Sure, most of the families with kids head off-Island and back to school, but the folks who come during the month of September are some of the luckiest visitors to Martha’s Vineyard.

Here are just a few reasons why: 

1. Incredible Weather 
September boasts some of the best weather of the year on Martha’s Vineyard. With a general decline in high heat and humidity, the Island enjoys warm, dry days. And since the waters have had all summer to heat up, they’re at their warmest temperatures of the year, which makes swimming simply magical. Plus, being located within the Gulf Stream allows for a lovely and gentle breeze.
2. Less Crowded Beaches
Speaking of amazing weather, September is the perfect time to hit up the beaches of Martha’s Vineyard! And with the majority of kids back to school, the beaches tend to have fewer crowds, which means more sand for you. What’s more, many of the private beaches that are “resident only” become open to the public during the month of September.
3. Great Deals (we coordinate your Land and Sea arrangements)
Peak season might be from Memorial Day to Labor Day, but that also means it’s peak prices on Martha’s Vineyard. Whether it be hotels, B&Bs, or countless unique and independent shops and galleries, prices generally begin to fall in September — making visiting the Island more affordable.
4. Easier to Get Dining Reservations
Visitors can often wait hours in August to get into the many award-winning restaurants on Martha’s Vineyard, but September guests don’t face this problem. Making a reservation at a delicious farm- and sea-to-table restaurant that sources outstanding local ingredients right from the Island is much easier to do in September.


5. Tons of Festivals
 September is the month of festivals on Martha’s Vineyard! The first weekend kicks off with the Martha’s Vineyard Jazz and Blues Festival, then the month continues on with the Martha’s Vineyard International Film Festival, the October Martha’s Vineyard Wine Festival, the Wampanoag Powwow, the Martha’s Vineyard Striped Bass & Bluefish Derby, and the Martha’s Vineyard Craft Beer Festival.

Festivities also includes Fall for the Arts, an arts & culture campaign that kicks off in September and includes events hosted by the Martha’s Vineyard Playhouse, Featherstone Center for the Arts — including the incredible Iron on the Island event — Tivoli Day in Oak Bluffs, the Soul Summit at Lola’s, Pioneering Pizza by Farm.Field.Sea., and so much more.