Seaside bike paths, whaling lore, a stunning island stroll, and more. Here are 10 of our favorite reasons to love the charming island of Nantucket.
By Yankee Magazine
Apr 06 2021
There are so many reasons to make a summer escape to the Cape and Islands, in fact, that we filled more than two dozen pages of Yankee’s May/June 2019 issue with a selection of our favorites, including things to see, things to do, and things to eat. Headed to the island of Nantucket? Here’s a look at 10 of our top reasons to visit.
In a welcome contrast to most of New England’s ocean communities, virtually all of Nantucket’s 110-mile coastline is free and open to the public—including 80 miles of some of the world’s most beautiful beaches.
Of all the celebrities summering on Nantucket, none are as welcoming to paparazzi as the tall ship Lynx, a handsome replica of a topsail schooner that sailed as a privateer during the War of 1812. Snap a photo as it glides through Nantucket Harbor in July and August—or better yet, climb aboard for a trip back into maritime history.
You can be on a dude ranch in Wyoming and step out in your favorite faded red-to-pink trousers, and immediately everyone knows where you’ve been—and a little something about who you are. The island’s signature clothing line began in the 1960s not long after Philip C. Murray took over his father’s Main Street clothing shop. Today, Murray’s Toggery Shopremains the only place on the world that’s legally allowed to claim it sells authentic Nantucket Reds attire.
There’s a party every day at Cisco Brewers, located in the small agricultural “heartland” southwest of town. Starting at 11 a.m. (noon on Sunday), visitors can grab a seat in the breezy courtyard, enjoy house-made beer, wine, or spirits, and find a nosh among a rotating lineup of food trucks (we love Raw Bar Yoho’s oysters and bluefish pâté). Live music starts at 3, then the whole thing wraps up … until the next day.
Beginning in the picturesque fishing village of Siasconset and ending at the Sankaty Head Light, the mile-long ‘Sconset Bluff Walk offers up different identities. Here, you’re on a narrow village road. Next, you’re cutting through scrubby forest. Now, you’re strolling across the manicured backyards of tony seaside estates. There are beach roses and birds, hydrangeas, and, of course, stunning views of an endless Atlantic.
On Nantucket, cycling routes fan out from downtown in every direction. To Madaket. To Surfside Beach. To Wauwinet. Of the 30-odd miles of paved paths here, the longest (and arguably most scenic) is an 18-mile round-trip that begins downtown and heads east, parallel to Polpis Road, to the sea. Bring your bike or rent from a number of local outfitters—most notably Young’s Bicycle Shop, overseen by third-generation owner Harvey Young just steps from the ferry landing.
For the better part of a century, Nantucket was the world’s whaling capital. The dangerous but lucrative industry made it one of the wealthiest communities in America and left every captain’s house, lighthouse, and harbor with a tale worth telling. Learn even a few of them at the Nantucket History Association’s Whaling Museum, and your sense of the island will be transformed.
Want a souvenir that skews a bit more heirloom than an “ACK” sticker? Nantucket’s signature lightship baskets, first made by crews on the island’s 19th-century floating beacons, are still available today from local artisans (a good place to start: Four Winds Craft Guild). Another only-on-Nantucket find: ultrafine throws and blankets handwoven at Nantucket Looms since 1968.
Given the homemade doughnuts at theDownyflake, comfort-food classics at Black-Eyed Susan’s, and budget bites at the old-school Nantucket Pharmacy lunch counter—you may be on vacation, but you definitely won’t want to sleep in.
Nantucket may be laid-back, but its outsize slate of special events means it’s anything but sleepy. Among the standouts are the Nantucket Book Festival, whose featured authors include Susan Orlean; the Nantucket Film Festival; and the Nantucket Comedy Festival. Martha’s Vineyard has plenty of high-profile celebrations, too, such as the magical Grand Illumination night.
See a full list of the islands’ summer highlights:Top Summer Events on Nantucket and Martha’s Vineyard
This content first appeared in Yankee‘s May/June 2019 issue.