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Should Your First Trip to Martha's Vineyard be During Summer or the Offseason?

When people think of Martha’s Vineyard, they imagine lovely beaches and seaside towns full of couples and families enjoying the summer sunshine, and can’t imagine another time of the year people would visit the island. While summer on the Vineyard is the iconic trip idea (to the point where everyone refers to the non-summer months as the “offseason”) travelers looking to come to the island for the first time could have an even better time in the offseason. So, should your first trip to Martha’s Vineyard be during the summer or the offseason? We’re going to run down some of the major qualities of both periods and you be the judge!


Why Your First Visit to Martha’s Vineyard Should be During Summer

  • The Full Beach Experience: The picturesque beaches of Martha’s Vineyard are at their best when you can take a swim on a hot summer afternoon. All of the beaches from Lucy Vincent to South Beach and the Oak Bluffs Town Beach have a different feel to them and you’ll only get the full beach experience when you visit during the summer. Sure you can try and take a swim in the ocean during your Thanksgiving visit but we wouldn’t recommend it!

  • Peak Island Nightlife: The summer season is when the nightlife scene on Martha’s Vineyard is thriving. Many tentpole bars and activities are only open during the summer season, so you’re missing out on the full potential if you come during the offseason. If you’re looking to have an ice-cold drink down by the harbor and do a bit of bar crawling with your friends or family on your vacation then make sure you make your first trip to the island during the summer!

  • Major Annual Events: The biggest events of the year on Martha’s Vineyard happen in the summer, and many tourists plan their trips around each one of them. The annual Agricultural Fair is a fantastic pop-up-style event that’s fun whether you’re here with your family to go on rides and play games, or if you and your significant other are looking to chow down at the many food stands. Illumination Night is an incredible experience you’ll only get on Martha’s Vineyard in August, where every gingerbread house in the campgrounds lights up in a major way. And of course, there isn't a better spot to enjoy fireworks than on a beach for the 4th of July!


Why Your First Visit to Martha’s Vineyard Should be During the Offseason

  • Peak Time for Tranquility: First and foremost, if you’re looking to get some real peace and quiet on your vacation then you should definitely visit Martha’s Vineyard in the off season. With nothing resembling a major city or highway, days and nights on the Vineyard are extra relaxing. The past two years have been tough on all of us, and if you prioritize rest over partying or swimming at the beach then the offseason on Martha’s Vineyard is the place for your vacation. 

  • The True “Islander” Experience: Even though everyone says that summer on Martha’s Vineyard is the best time to be there, there’s something to be said about the true “islander” experience that only year-round residents - and people who make the trip during the offseason - will get to see. That quiet early morning walk on the beach followed by a great cup of coffee at Mocha Motts, the peaceful and scenic drive up-island to explore Chilmark and Aquinnah, and so many more calm moments. While you can do similar things in the warmer months, the overall “islander” experience can’t be replicated in the summer season.

  • All of the Sights and None of the Crowds: The Gay Head Cliffs, Ocean Park Gazebo, and sunsets on Menemsha Beach are essential sites for any first-time visitors. They’re here for everyone year-round, but when the population of the island explodes in the summertime getting that perfect picture becomes a lot more difficult. There’s something extra satisfying about getting all of your vacation shots without crowds of people in the background, and that’s an experience you’ll only get during the off-season!

There’s our list on why you should visit Martha’s Vineyard for the first time during the summer or the offseason. Regardless of when you decide to come to the island, we can’t wait to see you!  If you’re planning a trip to the island make sure to check out our variety of vacation rentals or reach out to us directly for any questions about the best places to stay on Martha’s Vineyard!

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