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The Cliffs at Aquinnah Martha's Vineyard

How to Have the Perfect May Weekend on Martha’s Vineyard

The secret to a crowd-free, perfect weather weekend on Martha’s Vineyard? Visit just before Memorial Day weekend, when (almost) everything is open, the sun is shining, and the crowds are gone.


Catch the Steamship Authority ferry from Wood’s Hole, an easy 45-minute cruise from the mainland to Martha’s Vineyard. Fares are an affordable $17 for the round-trip journey. Traffic down to Cape Cod is much lighter in May than during the summer, but you’ll still want to give yourself a bit of a cushion, as the parking for the Wood’s Hole ferry is about 15 to 20 minutes from the main terminal. Free shuttle buses are provided, but be sure to check the Steamship Authority’s website on your drive to see which lots are open.

Check in at the Harbor View Hotel, located a five-minute walk from downtown Edgartown. Drop your bags and walk across the street to the Edgartown Lighthouse. Take a sunset stroll along the beautiful sandy beach before heading back to the hotel for dinner at Roxana, a tapas-style restaurant with an Asian and Mediterranean fusion vibe.


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During peak season, you might have to fight for a table at Rosewater Market, but in mid-May, you can stroll right up even during peak brunch hours and grab a sunny spot in the outdoor courtyard. People-watch while you enjoy fresh coffee, pastries, and breakfast sandwiches.

Borrow one of the Harbor View Hotel’s complimentary guest bikes (or bring your own on the ferry) and spend the day exploring Martha’s Vineyard’s many bike paths. This map is a great guide to the paths, indicating which trails are dedicated off-street and which are for experienced riders.

Start with the peaceful and flat seven-mile loop from Edgartown to South Beach. South Beach makes a perfect rest stop where you can lounge on the sand and watch the surf. Depending on how hardy you are, you can cool off here with a dip—I saw a few brave souls swimming when I visited in May.

If you’re up to continue your bike tour of Martha’s Vineyard, the State Forest loop is the longest off-street path on the island. This 10-mile trail winds through the protected forest, showing off more of Martha’s Vineyard’s natural beauty. On a gorgeous Saturday in May, I saw less than five other people on the trail—another reason to visit in shoulder season.

It’s easy to connect from the State Forest Loop to the Oak Bluffs to Edgartown trail, so you can spend the rest of your afternoon exploring the lively town of Oak Bluffs. Reward yourself with a slice of pizza from Giordano’s Restaurant, followed by a scoop of decadent homemade ice cream from Mad Martha’s.

If lunch has re-energized you, complete the Oak Bluffs to Edgartown trail back to the hotel, stopping off halfway at Bad Martha’s, a small brewery with a literal beer garden (it shares space with a plant nursery, so you can sip on a craft brew surrounded by plants and flowers). Or, if you’re done for the day, know that all of the public buses on the island are equipped with bike racks.

Finish off your day by heading west to the Aquinna Cliffs, where you’ll find some of the most spectacular sunsets on the island.


Grab the supplies for a picnic from Katama General Store, and hop back on your bike. The Chappaquiddick ferry is just down the street, and it might just be the shortest and most picturesque ride of your life. Don’t worry about a schedule—the On Time II and On Time III are always “on time,” as the ferries simply run back and forth from Chappaquiddick to Edgartown all day long. In shoulder season, there’s no need to wait in line—you’ll be able to easily walk on to the next boat and relax for the 527-foot journey.

Although there are no dedicated bike paths on Chappaquiddick, traffic is very light on the island and you’ll mostly have the street to yourself. I say “street” because there is just one paved road on the three-mile wide island (the rest are sandy and unpaved). Follow the main road to the tranquil Mytoi Garden, a secluded Japanese-style sanctuary that is free to visit, and full of beautiful plants and quiet spaces.


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Continue following the street to the end of the road to the Cape Pogue Wildlife Refuge. Here, you’ll find more than 14 miles of sandy walking trails, a pristine beach, and maybe one or two other visitors. There are no restaurants or cafes on Chappaquiddick, so this is where your picnic supplies will come in handy.

I visited Martha’s Vineyard the weekend before Memorial Day weekend, and enjoyed a mix of summer and spring-like weather (one hot and sunny day, one breezy day). The entire weekend, I never had to wait in line or wait for a table, and at times was the only person on a beach. Nearly the entire island was open, with the exception of a few shops and cafes which hadn’t yet opened for the season. Hotel prices are generally cheaper during this period as well.

If you’re looking to visit Martha’s Vineyard in a more affordable way and without the crowds, I highly recommend coming in mid-May.

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Caroline Morse Teel was hosted by the Martha’s Vineyard Chamber of Commerce and the Harbor View Hotel. Follow her on Instagram @TravelWithCaroline for photos from Martha’s Vineyard and around the world.

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