Photo by Mark Roessler

The stores and shoppers along Portsmouth's Market Street

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When I was a kid, Portsmouth was a quick blur seen from the Piscataqua River Bridge. Racing along in the back seat of the family car, heading north on Interstate 95 for vacations, I'm not certain I ever paid much attention to the town.

A couple of freighters might have caught my eye as they weighed anchor and dwarfed the surrounding centuries-old brick buildings, or I might have spotted a warship or submarine in dry dock at the imposing Portsmouth Naval Shipyard on an island in the bay. But, crossing that lofty bridge, I was far more concerned with reaching Maine on the other side. I never had much attention to spare for New Hampshire's biggest port city until I got older, and neither did most of New England.

Since then, though, I've lived near the city and made friends with many people living there. I even eventually got married in Portsmouth to a girl from the Granite State. She and I return to visit our friends frequently, but also to touch base with the many places we grew to love. One of the best New England beaches is hidden near Portsmouth, and the home of my favorite breakfast in all the land can be found only in that city.

When I was first getting to know Portsmouth in the 1990s, it was up-and-coming.

Before I'd ever stopped there for long—fifty years ago, when the shipyard had been running at full steam—the city had been a bustling international port. The quaint stone houses that are now vacation homes and have BMWs parked on narrow cobbled streets out front once housed the working class families that were employed by the Navy in the bay, and later out at Pease Air Force Base, west of town. Instead of working to attract tourists by trading on its antique charm, the city routinely played host to out-of-towners who had money to burn and were starved for less refined entertainments.

Though Portsmouth was famous for the work done there—it's the oldest continuously running naval shipyard and the area has a long tradition of shipbuilding—until the last few decades, the city had not generally been considered a family vacation destination. It was a rough town.

Having been off the radar of real estate agents for so long, little major development had occurred in the downtown and the historic character of the city had been largely left intact. During the 1980s, as the military installations began to down-size, middle-class families began moving into town, and the city began transforming.

These days, the up-and-coming city has arrived.

Property recently made available out at the former Air Force base generated a flurry of new, successful startup businesses, and a new rail line between Boston and Portland, Maine has turned Portsmouth into a hybrid: incubator for new industry, suburban community, and tourist destination. But while the city booms, the middle-class families who had moved in a couple decades ago, relishing the inexpensive historic homes and the thrill of a blossoming arts community, are starting to look elsewhere. In the past few years, several close friends of ours have moved out of Portsmouth to quieter, more affordable places. One couple has moved from a house with a yard about ten minutes from downtown Portsmouth to a small apartment in Queens, New York.

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Even if the place is no longer New England's best-kept secret, Portsmouth is absolutely worth a long, lingering visit. Whether you're spending a night in one of the area's many inns and hotels, or you're just buzzing through and want to take a quick look, consider the following suggestions.

Park your car on the edge of town. Downtown is crammed with traffic looking for the exactly same magic spot you're after. Save yourself the grief and confusion. There's a big parking garage centrally located, and the city's not so big: anywhere with on-street parking is a short walk to town. The city was built for walking, and it's best enjoyed that way.

Not all the best shopping is to be done at the outlets in Kittery, a few miles up the road. Portsmouth is full of boutiques selling the kinds of clothing, shoes and jewelry you might see on Newbury Street in Boston, and if you want second-hand books, music, or antique furniture, there are many excellent options to be found for the looking. There are bookstores at the end of State Street near the bridge, and Bull Moose Records is on Congress Street. For weird gizmos and plastic crap that will make you laugh, try Marco Polo's on Market Street.

The chief tourist attraction is Strawbery Banke, a museum neighborhood of preserved homes occupying an idyllic patch of land near the water. Homes representing a wide range of historic styles are open for visitors to explore their period-perfect interiors. It's well worth a visit, but not all the homes are original to Portsmouth. If you want to see what the old city looked like, wander the streets south of Strawberry Banke.

There is nowhere to swim in the bay within city limits (the tides are notoriously strong and dangerous), but there's a wonderful beach on New Castle, a small village on an island just a few miles outside of town. Take Route 1B from just outside Strawbery Banke through the old part of town and along a string of smaller islands that offer a good view of the shipyard and the huge, ominous naval prison. After winding through the streets of New Castle, you'll pass a turnoff for Fort Constitution and the Portsmouth light house. A quarter mile further on the left is a small community park, the Great Island Common, where for a small fee you can park and swim. Continuing along Route 1B from the beach, you'll soon come upon the famous Wentworth by the Sea Hotel, a hulking Victorian hotel that spent many years neglected and frightening, but has since been restored and is regal again.

Several restaurants around town feature live music on the weekends, and sometimes the wonderful, granite Unitarian Universalist Church on State Street has singer-songwriters perform. The most exciting venue to see a performance or a movie, though, is the Portsmouth Music Hall, recently given a multimedia makeover that has turned its lobby into something Jules Verne might have imagined had he been listening to Jimi Hendrix while sipping absinthe. Even if whoever is performing that night isn't your cup of tea, there's a full bar where you can enjoy the other-worldly space with a glass of wine.

There are dozens of fine restaurants in Portsmouth to choose from for dinner, but there's really only one option for late-night snacking: Gilley's PM Lunch. It's in a cramped trailer hidden in a corner behind the parking garage, but the greasy hamburgers are exactly what the doctor ordered when the early morning munchies take hold.

There's also only one real breakfast option: The Friendly Toast. The restaurant opened when my wife and I first came to the area, and it was originally located in Dover, not far from our apartment. It quickly became our favorite restaurant, particularly for breakfast. After expanding to a number of other venues around the seacoast, it finally landed right in the heart of downtown.

The place is decorated with bizarre, sometimes disturbing pop-culture relics unearthed from seedy garage sales and fringe flea markets. Bad amateur oil paintings are featured, along with board games and toys. Meals are served with mis-matched plates, mugs and cutlery. A team of tattooed and pierced staff runs the place with humor and efficiency, and judging by how the same faces keep appearing with my eggs and coffee whenever I visit, they seem to like working there as much as I do eating there. The menu is full of strange but appetizing options, and I'm told by those who don't eat meat that they do vegetarian "right." My perpetual favorite, though, is their Green Eggs and Ham, with pesto mayo and poached eggs on a huge slab of Canadian bacon, and a slice of toasted Anadama bread. Oh, and their home fries, heavy on onion, are beyond compare.

Further south on the short sliver of New Hampshire coastline is the town of Hampton Beach, with its famous boardwalk and Casino Ballroom. For a carnival-like atmosphere with the thunderous rumble of fireworks to punctuate your evening's entertainment, it's the place to be. Similar fun can be found to the north, along some of the beaches in Maine. But for somewhere more comfortable, laid-back and civilized, take a stroll around Portsmouth.