5 Best Things to Do on Nantucket

At 3½ miles by 14, Nantucket may be a bit bigger than what many people imagine when they think of an island — it takes a bit of effort to grasp it all at once. But with its boat-filled harbor, beautiful beaches, and weathered-shingle houses snuggled together on twisting lanes and cobblestone streets, this famed Massachusetts destination has a sense of “islandness” that neither size nor summer crowds can dispel.

You could easily spend a week or more exploring this former whaling capital turned vacation getaway. But if you have just a day or two, here are the five best things to do on Nantucket, Massachusetts.

5 Best Things to Do on Nantucket, Massachusetts

Go Exploring by Bike

The best way to delve into Nantucket is by bike. The island is flat and easily prowled, especially on the handy network of paved bicycle paths that fan out from downtown in every direction. You can bring your own bike over by boat (there’s a small charge) or rent a two-wheeler on the island 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. Once outside of Nantucket Town, the island has a welcome openness of space, with cranberry bogs and pristine sandy beaches and views seemingly to Portugal. Take the 3½-mile pathway to lovely Surfside Beach, and spend a day exploring the restless border between sand and surf.

Visit the Nantucket Whaling Museum

Nantucket was the Houston of its day, back when whale oil lit the lamps and greased the wheels of industry. From the majestic skeleton of a sperm whale to delicate scrimshaw, this museum tells of the historical hunt for leviathans and our modern quest to save them. Don’t miss the skeleton of the 46-foot-long sperm whale that washed onto Nantucket in 1998. Admission also covers a visit to Hadwen House, built in 1846 by whaling merchant and silver retailer William Hadwen at the peak of Nantucket’s prosperity as the whaling capital of the world. It’s one of the most elaborate examples of Greek revival architecture on the island and the only publicly accessible mansion of its age in the area.

FYI the Nantucket Historical Association manages these sites as well as others that are free and open to the public, including  the 1686 Oldest House and the 1746 Old Mill (the oldest functioning mill in the country); the association also offers walking tours in town. History buffs will also want to visit the old African Meeting House, once the central gathering spot for the African American community of the 19th and early 20th centuries.

Stroll the ’Sconset Bluff Walk

For more than a century in Nantucket, Massachusetts, visitors and residents alike have been able to enjoy one-of-a-kind access to the stunning ocean views at the island’s easternmost tip via the ’Sconset Bluff Walk. Thanks to civic-minded developer William J. Flagg, this traditional path has remained open to the public even as the shoreline filled in with private homes. 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. 

Join the Beach Scene

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. These stretches of sand are also protected by Nantucket Sound, which means warmer water for those who aren’t big fans of the chilly Atlantic surf. One of the most-photographed spots on the island is Brant Point, whose small beach at the mouth of the harbor is ideal for lounging and watching the boats come and go. There are many more beaches to choose from, but here are a few of our favorites: Steps Beach (picturesque and sunset-worthy), Children’s Beach (family-friendly activities and shallow water), Cisco Beach (biggest waves, with surfing lessons available), Surfside Beach (a popular spot that boasts a snack bar), and Sconset Beach (beautiful sunrises and quiet atmosphere).

Nantucket sunsets are breathtaking, and no visitor to the island should skip watching the day end at Madaket Beach. There’s no land on the western horizon to get in the way of the show — just open water and a view that will make memories to last a lifetime. Named a 2016 Yankee Editors’ Pick for “Best Beach for Sunsets.”

Shop for Nantucket Reds, and More

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 clothing shop on Main Street. Today, Murray’s Toggery Shop remains the only place on the world that’s legally allowed to claim it sells authentic Nantucket Reds attire. After checking out this icon, stroll the cobblestone streets of downtown Nantucket to discover such local gems as Nantucket Looms, the place for all cottage-style living essentials; Blue Beetle Nantucket, offering everything from monogrammed apparel to jewelry and home items; and Four Winds Craft Guild, which stocks artisan-made Nantucket lightship baskets among other handcrafted treasures. The Hub is a quirky shop filled with gifts and books that also has penny candy for kids and coffee for adults, while Mitchell’s Book Corner is frequented by bookworms and beloved Nantucket authors.

After a busy morning of browsing, catch the free shuttle to Cisco Brewers’ dog-and-kid-friendly mini-village outside town, where Nantucket’s only craft brewery and its sister winery and distillery showcase their liquid artistry amid live music and the island’s best food trucks. Seats at beer hall-style communal tables under the sun are quickly claimed by fans of Cisco’s unique beers, which include Gripah, a grapefruit IPA that drinks easy as a day at the beach. Named a 2019 Yankee Editors’ Pick for “Best Brewery Experience.”

Have your own list of the very best things to do on Nantucket? Leave your picks in the comments below!