Marblehead calls itself the Yachting Capital of the World, which sounds impossibly over the top, until you realize how seriously they take sailing here. This town of fewer than 20,000 residents is home to five yacht clubs and has produced a slew of world-class sailors, including America’s Cup winners Ted Hood and Robbie Doyle. How much do they love this sport? So much, they do it even in winter. It’s not uncommon to see sailors out in Marblehead Harbor, tacking and jibing in a biting February wind, in dinky two-person boats. They call it “frostbiting.” If this doesn’t sound like your idea of a grand time, no worries. This postcard-perfect seaport, just 25 miles north of Boston, offers landlubber pleasures, including boutique shopping, good restaurants, and pretty seaside strolls. And dress is preppy-casual.
An oceanfront bed-and-breakfast is the way to go here, and there are several good options. The Harborside House, in Old Town (23 Gregory St., 781-631-1032, www.harborsidehouse.com, rooms $90-
$125) is a charming 1850s home, with two guest rooms. The Harbor Room has an ocean view but twin beds; the Garden Room has a full-size bed and a minimum of froufrou. It’s a short walk to the harbor and shopping. Guests rave about host Susan Livingston and her homemade baked goods. Marblehead Neck is home to some pricey real estate — and a lovely (and pet-friendly) B&B, the Seagull Inn (106 Harbor Ave., 781-631-1893, www.seagullinn
.com, from $140-$250 per night). Located steps from Castle Rock, the inn offers three guest suites, including one with its own kitchen.
For seafood with a view, you can’t go wrong with
The Landing (81 Front St., 781-639-1266, www.thelandingrestaurant
.com, most entrees $9-$22) on Marblehead Harbor. Entrees like monkfish tacos win raves from regulars and tourists alike. They build a mean (grass-fed beef) burger, too. The clubby Three Cod Tavern (141 Pleasant St., 781-639-3263, www.threecod
tavern.com, most entrees $12-
$22) has absolutely no view except what’s on your plate — but that’s not so bad! Start with cornbread made from scratch, and then dig into a pile of fried oysters, crab cakes, or the excellent lobster roll. Or go light, maybe a Caesar salad topped with a whole fillet of grilled salmon. Tucked behind a muffin shop in Old Town, the Jack Tar American Tavern (126 Washington St., 781-631-2323, www.jack
tarmarblehead.com, most entrees $10-$22) is worth discovering, especially for chef-owner Scott Brankman’s flatbread pizzas. Try the lobster-topped pie or the fabulous bleu cheese-pancetta pizza with balsamic glaze. Tip: half-price pizza specials run nightly from 5-7 p.m. The Barnacle restaurant (141 Front St., 781-631-4236, www.thebarnacle
restaurant.com, most entrees $14.95-$18.95) has an unusual claim to fame: Ocean waves crash right over the building during a nor’easter, they say. Still, it’s been here forever. This isn’t the place to come if you crave haute cuisine, but it’s a fun spot to settle in for a casual lunch or dinner — say, a cup of clam chowder and some steamers.
DURING THE DAY
Up for a cool-weather ramble? You can get to pristine Crowninshield Island (access is via Harding Lane, www.thetrust
ees.org) by foot across the shallows at low tide. To walk across the dry channel, arrive one hour before dead low tide and leave by one hour after to allow enough time to walk the short loop trail and soak up the views of the harbor, islands, and Fort Sewall. In fact, it’s a treat to walk anywhere around Marblehead. Amble the charmingly twisted streets of Old Town and admire the architecture, including a stunning collection of pre-1775 homes. King Hooper Mansion
(8 Hooper St., 781-631-2608, www.marbleheadarts.org), the circa 1728 home of shipping tycoon Robert Hooper, now houses the Marblehead Arts Association, a must-stop for art lovers. Check out exhibits displayed in four galleries, rotating on a monthly basis. Members’ work is available for purchase in the gift shop. A reception is held the first Sunday of every month from
2-4 p.m. Old Town’s Washington Street is chockablock with tiny, tony shops. Kids’ stuff is especially well-represented, thanks to shops like Hip Baby Gear (108 Washington St., 781-631-5556, www.hipbabygear.com/marble
head_ep_45-1.html), specializing in eco-friendly goods for tots, Scuppers for Kids (79 Washington St., 781-631-5221, www
.scuppersforkids.com), home of too-cute kids’ clothes, and Mud Puddle Toys (1 Pleasant St., 781-631-0814, www.mudpuddletoys
.com). Tricked out with old household supplies (was Martha Stewart the design consultant?), a cheeky boutique called She (86 Washington St., 781-639-9800, www.shemarblehead.com ) stocks fashion-forward labels like Johnny Was, and a fun jewelry collection. For cute party frocks, pop into Bobbles & Lace, next door. Don’t miss a stop at Spirit of ’76 Bookstore (107 Pleasant St., 781-631-7199, www.hugobookstores.com), an independent bookseller with loads of character. Featuring a great selection — including books by local writers, and seafaring tales — and comfy couches, it’s a North Shore classic.
Once described as “folk music’s living room,” Me & Thee Coffeehouse (Unitarian Universalist Church, 28 Mugford St., 781-631-8987, www.meandthee
.org) has hosted such acts as
Tracy Chapman, Odetta, Pete Seeger, and Melissa Ferrick for 42 years. The pub at The Landing (see above) has been Marblehead’s go-to joint for live music for as long as anyone can remember. It’s usually hopping on Friday and Saturday nights, and it’s a great place to discover a new act, like Renee & Joe, a classic-rock duo from Gloucester, who make regular appearances.