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Marblehead is rich with history and so much more. By, Meryl D. Pearlstein

Part commuter town, part historical masterpiece, Marblehead occupies an envious position, overlooking one of the most picturesque sailing harbors in New England. Tiny and tony, Marblehead fills a hilly peninsula 17 miles up the coast from Boston, a site fishermen sparked to when they set up rough-and-tumble headquarters starting in the 1600s.

With a collection of nearly 300 preserved Colonial homes-fishermen’s cottages, captains’ residences and merchants’ mansions that wind up and down hills in varying shades of paint trim-Old Marblehead (to distinguish it from the newer, less-distinctive part of town) stands out for history buffs as the perfect immersion into New England’s pre-Revolutionary past. Many of the oldest homes, dating back to the town’s 1629 start, have windows hung so low that you’d swear the term “Peeping Tom” was invented here. Instead, this is a town of jovial and serious sailors, a town where it seems everyone who has a sea-facing historical home also has at least three pairs of boating shoes and is a member of one of the town’s six yacht clubs.

Dubbed “The Yachting Capital of the World” as well as the “Birthplace of the American Navy” under Colonel John Glover and General George Washington, Marblehead has always been a magnet for ocean lovers and beachgoers. Today, more of a resort destination than a working fishing village, Marblehead beckons with chilly waters that sparkle during the town’s century-old mid-summer Race Week, with its historic and modern sailboats also enjoyed by landlubbers from high perches in Chandler Hovey Park, Fort Sewall, and Crocker Park. Come winter, the town becomes a New England postcard, with a month-long Christmas celebration that entices both residents and visitors.

In any season, Marblehead is a town for exploring. Head straight to Old Marblehead, park your car wherever you can (it’s not easy), and wander along the narrow, twisting streets and public “ways of passage,” admiring the gorgeous architecture and breathing in Marblehead’s glorious sea air. Read the historic plaques on the many homes from the 1600s, 1700s, and 1800s, and stop to visit the 1768 Jeremiah Lee House, a majestic Georgian residence that epitomizes Marblehead’s success in pre-Revolutionary commerce. Refuel with a bowl of chowder or some fried clams at Maddie’s Sail Loft, the sailor’s favorite, and imagine yourself getting ready to face the Red Coats or a long day at sea.

Marblehead’s active involvement in the American Revolution, and later in the War of 1812 and the Civil War, adds to the town’s historic importance and intrigue. Quaint, cultured, and proud, Old Marblehead hasn’t changed much in 400 years; residents today are as much in love with its beautiful coastline, sailboat-dotted harbor, quirky streets, and ocean charms as were its earliest settlers.

Winter Wonderland Marblehead is a hotbed of holiday activity-first and foremost of which is its annual Christmas Walk.

Salem might get dibs on Halloween, but Marblehead is all about Christmas. Tens of thousands of people flock to the town to share in the magic of Marblehead’s winter arts festival and Christmas events. Kicked off by a holiday shopping preview party to motivate residents to stay local for shopping, the Marblehead Christmas Walk event is officially christened on Friday night by the tree lighting and caroling at Abbot Hall. The next morning, Santa and Mrs. Claus arrive at State Street Landing in a lobster boat painted red (of course).

The festivity really starts “moving” with the high-spirited parade of costumed kids and residents later that afternoon. Accompanied by musicians, many making a special pilgrimage to Marblehead to participate in this event each year, the parade meanders from the landing to Washington Street and Atlantic Avenue.

This year’s 40th annual Christmas Walk is scheduled December 2-5 with events extending onto the two following Saturdays as well. An Artisans’ Holiday Marketplace, hayrides, and refreshments are highlights. There’s no need to do your Christmas shopping at the mall if you’re visiting Marblehead; the often nautically themed arts and crafts here are much more distinctive, and the hospitality, smiles, cookies, and warm drinks offered by residents are personal “gifts” that are hard to resist.

If the weather turns mild rather than wintry, you might even see people heading to the Causeway to watch the waves at Devereux Beach and collect seashells instead of count snowflakes. Thinking about catching the Marblehead holiday spirit? Book an inn or B&B well in advance so you won’t be disappointed.

What To Do

Hot spots to hit on your Marblehead visit.

Abbot Hall

The seat of Marblehead’s government also houses Archibald McNeal Willard’s famous painting, “The Spirit of ’76.” Outside, a small museum displays artifacts from the town’s maritime past. 188 Washington Street, 781-631-1000, abbothall.org.

Fort Sewall

Built in 1644 to protect Marblehead from pirates, the fort was later enlarged to ward off the British. The headlands area is now a public park with views of Marblehead’s lighthouse and harbor, harbor islands, and Cape Ann. Reenactment encampments of the historic Regiment take place yearly. End of Front Street, essexheritage.org/sites.

Spirit of ’76 Bookstore

Wonderfully untrendy, the landmark bookstore sells collections of historical and sailing literature, in addition to the usual suspects. 107 Pleasant Street, 781-631-7199, spiritof76bookstore.com.

Stowaway Sweets

Started in 1929, Stowaway Sweets is the real deal. Can’t get to Marblehead? Arrange to have a replenishment of your favorite pralines or melt-aways shipped home. 154 Atlantic Avenue, 781-631-0303, stowawaysweets.com.

Shubie’s

The 1948 landmark gourmet store’s selection of imported foods, baked goods, and specialty wines is irresistible. Assemble a perfect on-the-go New England meal, starting with some rich Vermont cheddar cheese on home-baked bread, washed down with an Ipswich IPA. Cap it off with a chocolatey Marblehead mint from Harbor Sweets filled with peppermint crunch. 16 Atlantic Ave., 781-631-0149, shubies.com.

The Barnacle

Don’t come here if you don’t like seafood. Those who do will enjoy fried clams, steamers, and hot boiled lobsters with a selection of local ales. 141 Front Street, 781-631-4236, barnaclerestaurant.com.

The Landing Restaurant

The Landing sits at the end of a working pier and serves one of New England’s best lobster rolls. It was also the setting for the Michael Douglas film Coma. 81 Front Street, 781-639-1266, thelandingrestaurant.com.

Harborside House

Susan Livingston’s antiques-filled home overlooks the harbor and offers two oversized guest rooms. Built as a residence in 1850, the B&B also has an outdoor garden area and patio. 25 Gregory Street, 781-631-1032, harborsidehouse.com.

Harbor Light Inn

This 21-room inn dates from 1729 and has a yard and a pool. Many rooms have fireplaces, canopy beds, and Jacuzzis. Parking is complimentary. 58 Washington Street, 781-631-2186, harborlightinn.com.

The Details

Date of Settlement: 1629

Date of Incorporation: 1649

Zip Code: 01945

Population: 20,439

Total area: 4.53 square miles

Median household income: $84,473

Schools: 5 public elementary schools; 3 public middle schools (including 1 charter school); 1 public high school; 3 private schools

Notable Residents:  Peter Lynch, investor and author; Ted Hood, yachtsman(former resident but now in Rhode Island); Susan Estrich political advisor (former resident); Shalane Flanagan, American distance runner (former resident)