Insider's Guide to Things Insiders Don't Need
Pick one up at Young's Bicycle Shop, on Steamboat Wharf, because they've been there forever.
TOP BIKE ROUTES
The sublime six-mile Hummock Pond loop starts just east of where Cliffs Road intersects with Madaket Road.
• For the best sense of the inland island, mountain bike the occasionally steep, three-mile-long Barnard Valley Road, from its start at the intersection of Hoicks Hollow and Polpis Roads. Take drinking water and a decent map and make your way across the moors to Altar Rock.
• Of the many paved bike paths, the Polpis Road route is one of the best. It winds alongside marshes and beside ponds and cranberry bogs, and passes the Lifesaving Museum.
Rumor has it the airport once ran out of jet fuel because Wall Street bonus-mavens were leaving their Gulfstreams running while they played a round of golf. The Miacomet and Sconset clubs are open to the public year-round, though tee times aren't easy to get. In fall, you can play at the otherwise private Sankaty Head course.
Get one for an afternoon or a week at Force Five Watersports (508/228-0700) or Nantucket Harbor Sail (508/228-0424).
From town, Boomie on "Absolut" on the wharf always comes back to the dock with a few "big ones." If you prefer to leave from Madaket, Tom Malezko is a fishing legend on-island.
All Points Bulletin: A bluefish or a striper has at some time been hauled out of the surf along every yard of Nantucket's south and east shores. But to be alone, try below the old military reservation at Tom Nevers. When in doubt about where to go, join the all-terrain armada at the points: Smith's and Great to heave big plugs into the surf, Eel to wade for bass with a fly rod.
The courts at Jetties Beach are open and ready to play with some camp options for the kids. Late in the season you can play at the Casino in Sconset on a first-come, first-served, leave-five-bucks-in-the-box basis. Westmoor is the private tennis-savvy club on-island, located off Cliff Road.
The longtime favorite is Gail's Tours, but consider also native islander Robert Pitman Grimes (508/228-9382), a descendant of one of the original settler families. For a more formal education, visit the fine museums run by the Nantucket Historical Association.
WALK THIS WAY
Left over from the days of looking for whale spouts from shore, the Sconset Bluff Walk is a studiously unadvertised public way that takes you right through the front yards of the island's choicest shingle-style masterpieces, rivaled only by those on Hulbert Avenue and Cliff Road in town. It begins deceptively enough: at the end of Front Street in Sconset is a sign that says FOOTPATH ONLY, NO BIKES, which appears to refer to a very steep and narrow trail heading down to the right to Codfish Park. The path you want is the less obvious one to the left, through the privet hedges and on along the lip of the land. Residents are accustomed to the parade of strangers, but if you do the bluff walk at cocktail hour, don't expect to be invited up onto the porch for a drink.
WHERE TO SHOP, ShoP, Shop!
With a few exceptions, the best shops lie in the historic heart of town, along Main, Federal, and Centre Streets.
IT'S IN THE BAG
Originally produced during long hours at sea on floating lighthouses, the Nantucket lightship basket is now an institution. The intricately woven lidded baskets can be found at practically every shop along Main Street, but the finest are sold by a few venerable craftspeople. The best sources are the Ottisons (170 Orange Street · 508-228-9345) and Nap Plank, who runs Nantucket Basket Works (14 Daves Street · 508-228-2518).
YOU'VE GOT THE LOOK
Nantucket regulars have their own fashion sense, which, if you are the type to return from safari in a dashiki, you are welcome to mimic. Gentlemen wear pink pants from Murray's Toggery (called "Nantucket reds") held up by belts embellished with pictures of whales. And surely no handbag complements a cashmere sweater set and a black headband better than a scrimshaw-topped lightship basket. (When in doubt, Gucci is always acceptable.) The young here opt for a single uniform—no socks ever, Oxford-cloth button-downs, chinos—and seem bred to know their place: paradise.
Since 1913 Murray's Toggery Shop (62 Main Street · 508-228-0437) has been home to the famous "Nantucket red" trousers, the Sperry Top-Sider, and everything else the locals have been wearing from the time they were in boarding school. Peter Beaton Hat Studio (16 1/2 Federal Street · 508-228-8684) is the source for those lovely straw hats with the upturned brim and wide ribbon you see all the women wearing. If the fog has rolled in and raised goose bumps, Cashmere Nantucket (32 Centre Street · 508-228-7611) is your savior.
NEED A HOUSE GIFT?
The best presents—Simon Pearce martini glasses, perhaps?—come from Bramhall & Dunn (16 Federal Street · 508-228-4688). For the truffles that spell trouble for anyone who says, "Hey, I'm on vacation, I'm going to eat what I want," there's Sweet Inspirations of Nantucket (26 Centre Street · 508-228-5814). Everyone stops at Nantucket Looms (16 Main Street · 508-228-1908) eventually, if not to buy handmade sweaters, then to read the sign with distances from Nantucket to various points around the world.
ON THE FARM
Where to go if you've got a hankering for fresh produce and feel like venturing beyond the wagons parked on Main Street every morning?Some may tell you that the popular stand at Bartlett's Ocean View Farm (33 Bartlett Farm Road · 508-228-9403) is the only place to go. They aren't wrong: it's purely a matter of opinion. For a more intimate vegetable experience, try the stand at Moor's End Farm (40 Polpis Road · 508-228-2674).
(or, how to sound like a local)
• The town of Siasconset is always pronounced "scon-sit."
• Sesachacha Pond is always pronounced "sack-a-juh."
• The Pocomo area begins with "pock," not "poke."
• Coatue, the scalloped spit of sand that creates Nantucket Harbor, has only two syllables: "co-too." The "co" rhymes with go.
• Madekecham is a valley and a beach, and you say all the syllables, as in "mad-a-ka-sham."
• Sankaty Head, with its cliff-top lighthouse and first views of the rising sun, rhymes with sanctity.
• Moped is pronounced "anathema."
• Martha's Vineyard is generally not pronounced.