Things aren’t cooling down at The Square just yet — join us during these crisp fall months for casual events and live music at The Square. Watch the world go by from our rocking chairs or make a date at Chesca’s for the perfect night out.

Music in the Square - Edgartown


The brisk temperatures of late fall only increase our warmth towards the island — spend autumn the right way with these Martha’s Vineyard events . In addition to the highlights here, take a look at our full island event calendar below.


October 29, 2016

Happy Haunting  Immerse yourself in the spooky spirit of Halloween with this ghoulish gathering. Every ghost, goblins, and littles witch will scream with delight at trick-or-treating around downtown Edgartown as well as a costume contest at Backwater Trading Co.


November 12, 2016

Grand Wine Tasting Each year, MV Wine & Spirits opens their doors for everyone to taste their incredible fall wines for free — along with fresh bread and cheese.


November 18-19, 2016

Annual Holiday Gift Show  On the hunt for that perfect holiday gift? Bring back an authentic island creation from the Featherstone Center for the Art’s Holiday Gift Show.


November 25, 2016

Fall Festival  Now in its 26th year, the Felix Neck Wildlife Sanctuary Fall Festival is a nature-filled romp held every year on the day after Thanksgiving. With hayrides, face painting, live music, food, wreath making, a weather station and crafts for kids, live animals, trail walk, there is fun to be had by the whole family!


December 8-11, 2016

Christmas In Edgartown Santa Claus is coming to Edgartown! From the annual parade to the lighting of the lighthouse to deals at your favorite Edgartown stores, Christmas In Edgartown is the holiday gift that keeps on giving.