Triathlete Tour Guide: Nantucket

This sleepy playground for New England’s well-heeled boasts a lively triathlon culture.

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This sleepy playground for New England’s well-heeled boasts a lively triathlon culture By Catherine Mallette.

Claire Murray was fond of saying of her fellow Nantucketers, “Any more laid-back and we’d be comatose.” Back in the ’80s, she ran a guesthouse downtown at which my sister and I, still in college, worked in the summertime.

And in a way, Claire was right. Work-weary refugees from Manhattan and other centers of commerce have a history of fleeing to the island to fall under its spell of isolated, tranquil beauty. Twenty-seven miles off the coast of Massachusetts and just 14 miles long and 3 and a half miles wide, Nantucket is a place to escape business as usual, McDonald’s and Walmart, billboards and even the ubiquitous Kardashians.

The tiny downtown, with its quaint cobblestone streets, is like a trip back to the 18th century. Nantucketers adhere to strict building codes to preserve the entire island’s status as a National Historic District. Take a drive from the village of Siasconset on the eastern edge of the island all the way to Millie’s restaurant in Madaket to watch the sun set, and you’ll see gray-shingled cottages dotting a countryside of rolling moors covered with bayberry and the pink blossoms of rosa rugosa. No developments. No malls. No way.

But those who know Nantucket also know that its people can be laid-back but are far from comatose. The lucky folks who inhabit this little “elbow of sand,” as Herman Melville described Nantucket in Moby Dick, are also, historically, people with a drive to succeed. Enterprising islanders turned a little farming community into one of the richest cities in the country from the early 1770s through the 1840s as Nantucket served as the whaling capital of the world. And when that gig dried up, the inhabitants reinvented their spit of sand as a resort for the rich, who came in their yachts and private planes to enjoy what Native Americans had dubbed the “faraway island.” Designating almost 45 percent of the island as conservation land, Nantucketers added golf courses, resort-style inns, high-end boutiques and spectacular vacation homes to the mix.

In the past few years, Nantucketers have been once again reinventing themselves, this time turning their luxury vacation spot into a destination for athletes who want to take advantage of the island’s rugged beauty.

Jason Bridges, president of the Nantucket Triathlon Club, describes a “new movement” afoot, sparked in part by the introduction of the Nantucket Triathlon, which launched in 2008 and will take place this year on July 21. The enthusiastic members of the club describe their home as the perfect place to swim, bike and run, citing calm waters on the island’s north shore, killer runs on the almost 100 miles of beaches, and “almost secret” mountain bike trails through conservation land.

Outdoor activities abound, most in the water, of course. Rent some equipment or sign up for lessons in surfing, windsurfing, kite-boarding, stand-up paddle surfing, sailing or kayaking. Or charter a boat and go fishing.

If you want to combine a tour with your love for cycling, try Nantucket Bike Tours, run by Bridges. He’ll take you through backstreets, talk about the island’s rich history and make sure you see great views of the harbor. He also offers tours that end at Cisco Brewery, a popular watering hole. (If the weather is uncooperative and you have to get your spin in, he suggests the new Nantucket Cycling Studio, equipped with RealRyder stationary bikes.)

For those hoping to get in on Nantucket’s more laid-back moments, grab a picnic lunch at Something Natural (be sure to get the Portuguese bread!). If it’s a foggy morning, head straight to the Whaling Museum, filled with artifacts from those seafaring days. Other great touristy options: a ghost tour at night, a star-gazing program courtesy of the Mariah Mitchell Association and, of course, a lazy day at the beach. At the end of a day in the sun, swing by the Juice Bar near the harbor for cold, creamy ice cream in a fresh, warm waffle cone.

The island also boasts a boatload of fine dining, including American Seasons, with its emphasis on regional and seasonal foods (also named most romantic restaurant on the island by Boston magazine last year), and Fifty-six Union, a place to see and be seen that’s popular among the island’s summer people.

One caveat about this New England Shangri-La: It can be difficult and expensive to find lodging during the summer. There are no chain motels; only guesthouses and inns. If you’re interested in the July triathlon for 2013, make your lodging plans as soon as you sign up for the event. The triathlon’s website lists local establishments that give discounts to racers.

And another caveat: If you’re bringing your bike for the race, be sure to get a reservation on the Steamship Authority ferry (see the triathlon’s website for discounts on the ferry, too).

Finally, no trip to modern-day Nantucket would be complete without a shopping excursion downtown. Get some Nantucket reds (red canvas pants) at Murray’s, pick up a lightship basket (a woven purse) and stop by Claire Murray’s eponymous shop for a hooked rug. See, even Claire wasn’t that laid-back. She now runs a mini home décor empire with 10 stores and multiple boutiques across the globe.

Nantucket Shout-outs

Members of The Nantucket Triathlon Club share some of their favorite things. (And if you’re on island, be sure to check their Facebook page for group rides, swims and runs.)

» Nantucket triathlon:
Mountain bike trails:
Kayak rentals: Sea Nantucket Kayaks,
Sailboat rentals and lessons: Nantucket Community Sailing,
Lap swims: Nantucket Community Pool,
Bike tours:
Picnic fare: Something Natural,; Cowboys Meat Market & Deli,
Millie’s restaurant:
Nantucket Cycling Studio:
Cisco Brewery:

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