Boston's Great Northern Border Town Road Trip

Make a salty escape to state line neighbors Portsmouth, New Hampshire, and Kittery, Maine.

Good fences, so we’re told, make good neighbors—but a good bridge can take that pearl of wisdom to a whole new level. Such is the case north of Boston on the New Hampshire/Maine border, where the Piscataqua River takes an island slalom towards the ocean. With an abundance of shops, oodles of history and a burgeoning foodie scene, Portsmouth, New Hampshire, is perfectly positioned for a day trip from Boston or, preferably, an overnight stay. Adjacent town Kittery, Maine, is just a short walk or drive over the Memorial Bridge and is home to outlet shopping, artsy bars and some of the finest fried clams in New England.

The Hotel Portsmouth

Red Bricks and Great Whites

Portsmouth is a quintessential New England town, with shops dotting bricked downtown sidewalks and the Market Square area. The Hotel Portsmouth makes a great base for exploration, located in the heart of town and featuring loft suites with rooftop views. Menswear and accessories shop Sault New England personifies classic regional style and sets the tone for the vibe and feel of Portsmouth. Along with preppy essentials like gingham button-downs and needlepoint belts, Sault also has an assortment of candles, note cards and even items for the family dog.

Wander through downtown Portsmouth to the less-traveled Ceres Street to stumble on the tiny vintage haberdashery, Old as Adam. Kitschy, cramped and overflowing with character, the store has a great collection of antique menswear: Think the best parts of grandpa’s closet neatly displayed on racks, tables and cases. From tie clips and cufflinks to leather jackets and boots, Old as Adam is as much an experience as it is a shop.

A further stroll down Ceres Street reveals one of the most photographed spots in Portsmouth. Located on the side of a run-of-the-mill one-story brick building is a striking mural—by street artist Shark Toof who has a thing about sharks, as his pseudonym suggests—depicting a great white, teeth bared, rearing maniacally out of the water while a nearby dove offers a sidelong glance of nonchalance-laced disdain.

Old Memorial Bridge

Bridge of Sighs

Venture across Memorial Bridge to check out Kittery, Maine, Portsmouth’s kindred spirit and "bonus destination." A worthy first stop is Blind Pig Provisions, with its ideal location alongside the Piscataqua River on Badgers Island. It’s a rustic tavern with a self-described menu of “funky BBQ, seafood and merriment.” On cool, crisp days, grab a local craft beer and take a seat in the Adirondack chairs on the back lawn overlooking the water.

In truth, Memorial Bridge is a destination in and of itself, especially at sunset when visitors look west to catch dramatic views over the Portsmouth Shipyard. Open to cars, pedestrians and bikers alike, the bridge raises for larger vessels, and during summer the lift section remains partially elevated every half-hour between 7 am and 7 pm for about 15 minutes to allow smaller boat traffic to pass. The views both east and west make Memorial Bridge a photographer’s dream.

Hang a left on Government Street after the bridge and you’ll soon happen upon a cluster of dock-adjacent restaurants and bars, including Anneke Jans (imaginative American cuisine and a great wine list) and The Black Birch, which will charm you with its easygoing community vibe and menu of locally amended classics. Opposite, sip a cocktail over Welsh rarebit at The Wallingford Dram, a cabin-esque boozer sprinkled with equal amounts of salt and sophistication.

Drive or bike a little further into Kittery and check out Bob’s Clam Hut for light and incredibly tender fried clams. A real New England institution, Bob’s roadside restaurant has been serving hungry visitors for more than 60 years.

Kittery also plays host to an array of outlet stores up and down Route 1. The most notable spot is Kittery Trading Post, which has outdoor gear for the adventure enthusiast as well as tourist knickknacks and fudge. The Lobster Pot, a seasonal outdoor eatery, is on site, and the picnic area is open year round.

Tuscan Market

Market Fresh

Back over the Memorial Bridge in Portsmouth, seek out Row 34, a chic, laidback oyster bar and seafood restaurant in a newly developed area of Portsmouth’s downtown. Boston is home to the original Row 34 (in the Seaport District) but its second location fits Portsmouth like a bespoke fisherman’s smock. There’s an expansive raw bar selection, expertly crafted seasonal cocktails and two types of lobster roll: the traditional mayo-based style, or the highly decadent, utterly delicious, butter-dipped Connecticut variation.

Naval history abounds in Portsmouth and the submarine USS Albacore is well worth a look. Starting in 1953, the vessel was used as a research sub, designed by the Navy to test experimental features until it was decommissioned in 1972. Today, it sits dry-docked in Albacore Park and is open to visitors for self-guided tours. Kids will love exploring all the hidden nooks and crannies of this historic vessel.

As the day comes to a close, stop at the new Tuscan Market on Route 1 and grab a snack for the ride home: cannoli, fresh bread or any number of classic Italian goodies. Prepared foods include pizza, panini and daily house-spun gelato. If you decide to stay on for one last meal, sister restaurant Tuscan Kitchen is right there. Why not raise your glass to good bridges?

Matthew Simko
About the author