Edgartown: Preppie Paradise

These days, instead of sailing on a small boat with college kids playing hooky from their summer jobs, I’m often on a slightly more comfortable boat with friends playing hooky from slightly more stressful jobs. But what hasn’t changed is that Edgartown remains the quintessential summer cruising destination.
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A lot has changed since I first sailed into Edgartown Harbor in the late 1980s. Back then I was squandering my youth sailing, going to the beach and waiting tables on Cape Cod. When the cutest waitress in town asked if I’d like to sail with her from Wellfleet down to “the Vineyard” on her father’s Hunter 25, I said “You betcha!” I was a bit disappointed when I met the other Ray-Ban bespectacled guys in her crew, but I was still psyched for the adventure—even if I was never going to get the girl.

These days, instead of sailing on a small boat with college kids playing hooky from their summer jobs, I’m often on a slightly more comfortable boat with the girl I was meant to get and with friends playing hooky from slightly more stressful jobs. But what hasn’t changed is that Edgartown is only a short hop from mainland Massachusetts and remains the quintessential summer cruising destination.

Nothing really compares to sailing past the colorful cabanas of the Chappaquiddick Beach Club and the stubby lighthouse at the harbor entrance on a sunny summer afternoon. Once you’ve dodged the car ferry that constantly zips back and forth across the channel, you’ll be directed via VHF to pick up a mooring that’ll set you back a cool $40 a night. But it’s well worth it, as the inner harbor is connected to Katama Bay, and the current is strong. Be warned that while the mooring field is quite large, it fills up on busy summer weekends, so it’s a good idea to reserve a spot well in advance (edgartownharbor.com). 

From there, Edgartown is an easy launch ride away, or you can take your chances finding a spot for your tender at the small dinghy dock in town. Either option lands you right in the center of the action, where you’ll see plenty of happy tourists, preppie locals, an occasional celebrity and maybe even a sitting President (he usually comes in August). Edgartown is a great place to explore on foot and shop for souvenirs and stylish clothes, if you’re into that kind of thing; there’s also a wide variety of restaurants to satisfy your gastronomical cravings. However, I’ve always found the best way to explore both the town and its environs is by bicycle. These can be rented right on Main Street (marthasvineyardbike.com) and are the perfect way to get the blood flowing after a long stint in the cockpit. 

One of my favorite rides is along the bike path out to South Beach. I also love slowly spinning around the uber-charming neighborhood over by Eel Pond off North Water Street. If you really want to get away from the boat and the “hustle and bustle” of town, you can take your bike on the ferry over to remote Chappaquiddick and ride all the way across the island out to East Beach. It’s a bit of a workout, but even when Edgartown is chock-a-block with tourists, you usually can have a good portion of the beach all to yourself. 

Lots of cool summer destinations offer stunning natural beauty, a great harbor, a sophisticated local community and first-rate shops and restaurants, but none do it quite like Edgartown. The only “problem” is you can’t experience all of this preppie paradise has to offer in one short weekend. I’ve been back several times since that eye-opening cruise back in the ‘80s, and it gets better every time.

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