Visiting Martha's Vineyard in the summer is something everyone should experience at least once in their lives. The beaches, the nightlife, and the quaint tranquil vibes come together unlike anywhere else in the country. While the island is very small compared to many other places you might go for vacation, each area of the island has its own unique flair and you may find yourself at the end of your vacation wishing you had spent more time in one place or another. To help guide your upcoming vacation we're going to give you an Islanders perspective of each one of Martha's Vineyard's incredible towns. By the end of this article, you’ll have a great starting idea of the unique aspects of each town to guide where you’ll want to spend your time when you visit the island during the summer!
Oak Bluffs is where you'll want to spend a lot of time if you're looking to experience the nightlife scene on Martha's Vineyard. While Oak Bluffs is a far cry from any sort of happening downtown destination in major metropolitan cities in the United States, the locals of Martha's Vineyard would certainly call Oak Bluffs “the party town” of the island. Circuit Avenue, the main downtown destination, hosts the Island's many popular restaurants, dessert spots, and bars. There's no better place on the island where you can easily walk off a beach and within five minutes be sharing a meal or some drinks with your friends or significant other. Additionally, this is an excellent location to spend time if you're bringing your family and have younger or teenage kids with you as Oak Bluffs has the highest concentration of “kid-friendly” activities on the island such as an arcade and the Flying Horses carousel, America's Oldest Carousel. And don't forget a freshly baked late-night donut from #BackDoorDonuts.
Vineyard Haven is the year-round “hub” of Martha's Vineyard. It's the only town where ferries arrive for the full year, and, as such, is often the location many travelers to the island see first when they arrive. Traditional travel logic in most parts of the United States would say that you don't really want to spend a lot of time in the town nearby the airport/way you traveled into the area you’re visiting. However, that is definitely not the case with Vineyard Haven on Martha's Vineyard. If you're looking for great restaurants and shopping locations with a little bit more of a low-key vibe compared to Oak Bluffs, then Vineyard Haven is a great place for you to spend time. Although Vineyard Haven isn’t a “dry” town anymore it was for many years, and consequently, Vineyard Haven doesn't really have that hustle and bustle nightlife scene you're going to find in Oak Bluffs or even Edgartown. So if you want to split the difference between a fully secluded island experience and having some convenience in shopping destinations nearby then Vineyard Haven is the place to be on your vacation.
Edgartown is a very interesting location on the island. It probably has the best publicly-available beaches when compared to Oak Bluffs or Vineyard Haven with Island favorites, like South Beach, covering a lot of ground to relax and have some fun in the ocean with the potential for the waves to get pretty big. Some Islanders may joke and refer to Edgartown as the “preppy” town on Martha’s Vineyard, and while you might see a few more folks wearing a polo shirt, no one in the town is looking to turn their nose up at you. Edgartown has some classic Island restaurants such as Dock Street Diner and The Wharf, offers some nightlife activities (though not as many as Oak Bluffs), and has a great mix of shopping destinations. The vast majority of shopping and restaurant options on Martha's Vineyard are exclusive to the island but Edgartown offers a local Lululemon, in addition to many island exclusive stores, as well if you find yourself in need of some quality yoga pants on your trip! Edgartown is a great location for shopping and dining on the island, but unlike Oak Bluffs, and Vineyard Haven, you're not going to be able to walk from the downtown area to a beach so keep that in mind when you're planning your time.
Up-island (West Tisbury, Chilmark, Aquinnah & Menemsha)
Why are we combining towns here? Well, a deep dive into West Tisbury, Chilmark, Aquinnah or Menemsha would shine a light on some differences between each of them. However, for the purposes of a traveler trying to take in the feel of the different areas of the island, looking at these three towns as the collective ”Up-island” is much more productive. Staying Up-island offers the absolute peak of tranquility that you can only get on Martha's Vineyard. There's no semblance of a downtown or Main Street type area anywhere Up-island, but that could be a very big benefit depending on what you're looking for on your trip to Martha's Vineyard. Additionally, the Up-island areas offer the best-in-class beaches Martha’s Vineyard has to offer although some of them aren't open to the public. Also, you can't forget about signature Island destinations like the Gay Head Cliffs or the legendary sunsets on Menemsha beach. If you're looking to unplug completely on your vacation spending time Up-island is the way to go, but just make sure you know that you aren’t going to be able to walk to more familiar downtown settings like Oak Bluffs, Vineyard Haven, or Edgartown from any of these Up-island towns.
Are you ready for some summertime fun and relaxation? If you're in need of a place to stay on Martha's Vineyard make sure to check out our rental properties or if you have any real estate-related questions you can reach out to us directly. We look forward to seeing you on the island this summer!