Every year there are many great festivals and gatherings on Martha’s Vineyard. Here are just a few highlights.



Martha’s Vineyard’s traditional way to warm up in February is The Annual Big Chili Contest. Held at the PA Club in Oak Bluffs to benefit local non-profits, entrants and chili fans from far and wide come to compete and judge in this mid-winter party and eat-a-thon. The Mariachi band gets you in the spirit and the fun goes all day.


Independence Day

Old school Americana at its best! Hot dogs and burgers on the Whaling Church lawn, antique cars and fun floats. Vineyard Square is the best spot to see the parade as it goes right past the front of the hotel. Then, stroll up North Water Street to stake out your spot for the fireworks.

  • Third Week of August. Not an official festival, but the BIG week of summer!
  • Illumination Night on Wednesday in Oak Bluffs kicks off the big weekend. This traditional night at the campgrounds began more than a century ago and the format remains — a community sing-along as dark falls then the lighting of the beautiful Chinese and Japanese lanterns that adorn the cottages. Not to be missed!
  • The Martha’s Vineyard Agricultural Society Fair starts on Thursday and runs through the weekend. Animal shows, crafts, and competitions, as well as the highlight of the show — the skillet toss — where local women compete to throw their skillet the farthest.
  • The Oak Bluffs Fireworks on Friday night are the biggest celebration of summer on Martha’s Vineyard. Gather in Ocean Park, where music in the Gazebo starts around 8:00 pm. Spectacular fireworks begin at dark. Take public transportation — buses run continuously between Oak Bluffs and Edgartown before and after the show — it is much easier than circling for hours looking for a parking spot!

Food & Wine Festival

October brings this annual culinary treat — workshops, tastings, wine dinners and the Grand Tasting make this a “must do” for foodies. Our location puts you at “Getaway Central” to walk to most of the main events!


Christmas in Edgartown

The second weekend in December brings caroling, horse drawn carriage rides, a parade and lots of holiday cheer to Edgartown. Breakfast with Santa on Sunday morning thrills the kiddies — Santa leaves the sleigh behind and arrives by Fire Engine. Check out some photos of Christmas in Edgartown party at the Square in this post from our Martha’s Vineyard blog.