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Vacation Portsmouth, New Hampshire

Tourist Guide

The Best of Both Worlds
New Hampshire's Hip and Historic Seacoast City

The Odd Showroom is one of many great clothing stores to be found in Portsmouth, New Hampshire
The Odd Showroom in Portsmouth


You'll be hitting the road today, taking advantage of Portsmouth's central location on New England's northern shore and its position at the gateway to New Hampshire. Ponder your options over pumpkin pancakes studded with Raisinets or what is unabashedly proclaimed to be New Hampshire's best omelet at The Friendly Toast, a quirky Portsmouth institution where you'll love perusing the advertising ephemera that graces eye-opening, cherry-red walls.

The Friendly Toast is a popular breakfast spot in Portsmouth, New Hampshire
The Friendly Toast

Shoppers will want to head just minutes north to Maine's southernmost town, Kittery, known for the factory outlet stores that line Route 1. More than 100 national retailers have a presence here, including children's wear makers like OshKosh B'Gosh and Hanna Andersson; high-end apparel labels including Tommy Hilfiger, Calvin Klein, Liz Claiborne and Polo Ralph Lauren; and sporting goods and home furnishings brands like Orvis, Crate and Barrel and Cuddledown. For lunch, dine at Robert's Maine Grill Break, which offers views of Spinney Creek, oysters galore and a classic Maine lobster clam bake. If you haven't worn out your credit card, more outlets and the L.L. Bean Flagship Store are just an hour farther north in Freeport, Maine. Lovers of fine spirits will also want to visit Cold River Vodka in Freeport. Distillery tours, offered Tuesday through Saturday year-round, explain the process by which Maine potatoes become Double Gold Medal-winning vodka.

The L.L. Bean Flagship Store is located just north of Portsmouth in Freeport, Maine
L.L. Bean Flagship Store

If you prefer to spend the day exploring New Hampshire's interior on a stunningly scenic drive, turn your wheel northwest and follow Route 16 to Route 11 to Route 28 to Route 109. In just an hour and a half, you'll be tracing the northern shore of the state's largest lake. Winnipesaukee is as glorious to behold as it is fun to say. While you may be tempted to linger in Wolfeboro, a charming lakeside town that has welcomed vacationers since Colonial Governor John Wentworth built a summer home here in 1771, press on, after a brief stroll through town. At the intersection of Routes 109 and 171 in Moultonborough, turn right to find the steep, two-mile entrance road to Castle in the Clouds, the mountaintop former estate of wealthy industrialist Thomas Plant. From mid-May through mid-October, spend time touring the granite-walled "castle," built in 1913 with unheard of modern conveniences; hiking miles of trails through the 5,500-acre property; and enjoying spectacular views of Lake Winnipesaukee's jagged shoreline. When hunger pangs strike, continue circumnavigating Winnipesaukee by traveling southwest on Route 25, then north on Route 3 to Meredith, where it's always Thanksgiving at Hart's Turkey Farm. On a busy day, Hart's serves more than a ton of turkey, 400 gallons of gravy and more than 100 homemade pies.

The stunning view from the Castle in the Clouds estate in Moultonborough, New Hampshire
View from Castle in the Clouds

America's oldest fishing port — Gloucester, Massachusetts — is due south of Portsmouth and just an hour's drive via Interstate 95, but you'll want to travel in the slow lane and follow Route 1 to Route 133 if this is the direction in which your wanderlust beckons. En route to Gloucester, stop for lunch at your choice of rival restaurants, Woodman's or the Clam Box of Ipswich, for a taste of the uncommonly delicious, golden deep-friend Ipswich clams for which this coastal region is famed. In Gloucester, where fishing is still a way of life, you can watch the boats come and go from the Jodrey State Fish Pier, learn about the city's marine life and history at the Gloucester Maritime Heritage Center and visit such landmarks at the Crow's Nest, a bar featured in Sebastian Junger's The Perfect Storm and its movie adaptation, and the "Man at the Wheel," Gloucester's Fisherman's Memorial Statue dedicated to "They that go down to the sea in ships." Leave time for a drive out to Rocky Neck, where you can pop in and out of artists' studios, conversing with the fascinating cadre of painters, sculptors, photographers and jewelry designers who continue a 150-year-old tradition as members of America's oldest continually working art colony.

The lobby of The Music Hall in Portsmouth, where everything from opera to stand-up comedy can be seen
Lobby of The Music Hall

Whether you feasted on lobster in Maine, turkey in New Hampshire or clams in Massachusetts, you won't likely crave more than a light nibble when you return to Portsmouth this evening. Two brewpubs, the Portsmouth Brewery, located on Market Street in the city center, or the Cataqua Public House at the Red Hook brewery, a four-mile drive from downtown, will fill the bill. Both offer standard pub fare, hearty ales and a chance to rub elbows with denizens, all while resuming your Portsmouth history lesson. Brewing was the industry that put Portsmouth on the map in the 1870s, after its seafaring glory days had waned.

For fine dining, try Black Trumpet Bistro, where chef Evan Mallet merges local ingredients with flavors from Northern Africa and Southern Spain, or Cava Tapas and Wine Bar on Commercial Alley, where innovation meets small plate style.

For evening entertainment, consider seeing a show at one of two historic venues. If you're lucky, your visit may coincide with an intriguing performance at The Music Hall, located on Chestnut Street in the heart of Portsmouth. This grand Victorian venue's programming ranges from opera and musical theater to stand-up comedy and intimate performances by well-known recording artists. Summer brings plenty of indie and classic films to get you out of the heat, and you'll also want to check the schedule at the Hampton Beach Casino Ballroom in nearby Hampton Beach. Popular artists and comedians now take the stage at this century-old dance hall, where all of the great Big Bands of the '30s played.


Portsmouth tugboats

(Updated: 09/13/11 NW)

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