Portsmouth, N.H.: The Unpretentious Underdog of New England


The author at Book & Bar, Portsmouth, N.H.

Mankind has a natural affinity for the underdog.

Endorsing dark horses is a humanistic trait, dating as far back as, and certainly beyond, the biblical showdown of David vs. Goliath.

It’s a psychological phenomenon that, according to research, helps explain the likes of the nation’s unbounded enthusiasm for March Madness, the worldwide popularity of Harry Potter, the meteoric rise of presidential candidate Senator Bernie Sanders and the surge of farmstand shopping over corporate supermarkets.

I would argue that the underdog role is one that can also be portrayed by locations, and that urban centers, for example, boast similar characteristics as those aforementioned. The Harvard Business Review described this twofold effect as having “a disadvantaged position… and a passion and determination to triumph against the odds.”

In that regard, Portsmouth, N.H. is the Northeast’s underdog city.

Portsmouth is stuck between a rock and a hard place, or rather quite literally between Boston and Portland, Maine — two major forces behind coastal New England commerce and culture.

Both Boston and Portland are regional Meccas for food, drink, art, history and all of the salty, seafaring idiosyncrasies native to our corner of the country.

Population-wise, Portsmouth is about one-third the size of Portland which, in turn, is about one-tenth the size of Boston. Portland has one of the highest rates of restaurants per capita out of any city of any size in the United States as well as a blossoming craft beer scene. Boston is the unofficial capital of New England, the socioeconomic engine that not only drives industry but ingenuity as well, not excluding any major sector.

What some people, including born-and-bred Bay Staters like myself, don’t realize is that Portsmouth is not only a quintessential hamlet that enjoys lively theatrics, award-winning eateries and authentic artistry like its bigger brothers;  It also possesses an underdog trait that these two do not: modesty.

For the first time in my life I visited Portsmouth, after spending the lion’s share of my life thus far living just 30 short minutes down I-95

The visit was prompted by an augmented adoration for Portland and perpetual affection for my hometown of Boston. When scouring Google Maps for which setting to drink in next, I explicitly had it in mind for a destination that’s unassuming, not loftily promoted and seemingly flies under the radar; but is one most assuredly fit for indulgency, imbibery, and discovery.

Portsmouth encompasses those qualities and then some.

Barely an hour north of Boston, Portsmouth is hardly the generalization of New Hampshire at large. With deep roots dating back to the age of European exploration, Portsmouth has grown into a far-left leaning municipality that values a liberal mentality, quality nourishment, historic preservation and an embracement of being the underdog — a stark contrast between much of the rest of the rural, conservative and self-assured Granite State.


Book & Bar, Portsmouth, N.H.

Perhaps no single place in Portsmouth embodies these qualities more than Book & Bar. The love child of a particularly saucy ménage à trois between a used book store, a cafe and a pub, Book & Bar can be found at the ground floor of the former customs house of Portsmouth, a granite Antebellum Era building at the corner of State and Pleasant streets.

Don’t let the cold, gray exterior fool you. Inside is a snapshot of all things Portsmouth: caffeinated beverages, locally-sourced brews and farm-to-table delectables that allow for any patron to digest the essence of Portsmouth while reading about its (or others’) legacy briefly or at length.

Book & Bar is a must-visit. It’s fairly priced menu for goods worthier of a heftier price tag and surprisingly vast literary spectrum make this the perfect perch for a morning, afternoon or entire day.

State Street and its parallel counterpart Daniel Street together act as the spine of Portsmouth. It’s here that many of the boutiques peddling handmade goods are situated, forming boundaries of the unofficial commercial district of the city, the epicenter of which is Market Square.

Lined with shops, galleries, landmarks and restaurants (including an unsuspecting number of Irish pubs), Market Square is the launching pad of Portsmouth, ready to send any traveler down Commercial Alley, a pedestrian walkway that’s also a microcosm of the city; toward the riverfront, which not only boasts its own arsenal of seafood joints but also the Seacoast Repertory Theatre; or Westward to Strawbery Banke, a living history museum along the lines of the pilgrim settlement Plimoth Plantation, Pierce Island or Four Tree Island, both havens for hikers.

The best advice I could bestow on any prospective visitor is to intentionally get lost. Portsmouth’s streetscape is laid out in similar fashion to Boston’s — nonsensically. There is a gridded pattern that brings order to vehicular drivers, but there are also passages and lanes that curve in and out, sure to tempt any passerby into wondering what tantalizing curiosity may be hiding around the bend.

It’s this philosophy that led to an abounding variety of locales, the volume of which one may not expect in such a humble community.

The Press Room is a brick and beam watering hole that outwardly exhibits Federalist style Portsmouth. This dimly-lit atmosphere fosters jazz nights, poetry readings, Irish shanty singalongs or really any form of art that thrives in would-be smoke-filled dives.

If ethnic diversity is what you’re after, 5 Thai Bistro, housed in the same building as Book & Bar, offers authentic Asian fare. This is the kind of place where the server’s nonchalant recommendation for medium-heat spice will set your mouth ablaze. Heaping piles of noodles, rice and applicable add-ons are hearty enough to sustain even the most famished stomachs.

For those keen on tipping the elbow, any restaurant will offer a fair share of locally brewed beers. For establishments like Portsmouth Brewery, Earth Eagle Brewings, British Beer Company, and Redhook Ale Brewery, homemade suds are their bread and butter.

In Portsmouth, taking the edge off is especially relaxing given the close proximity of all the bars and breweries, rendering the need for a designated driver near-obsolete — please don’t drink and drive but if you’re going to stay local, everything is within walking distance.

Despite an abundance of culture and character in Portsmouth, there’s one qualm I have: an accessible riverfront. The banks of the mighty Piscataqua is where Portsmouth was founded. It separates New Hampshire from Maine. In the middle of the river is an island upon which the historic and integral Navy Yard was built.

Not to mention, stunning views of the river offer a snapshot of what life on the craggy New England coast has to offer.


Memorial Bridge, spanning the Piscataqua River

The City of Portsmouth ought to consider what it would take to build some kind of promenade along the Piscataqua which would allow pedestrians and cyclists a seaside vantage for walking, running, biking and sightseeing that extends far beyond Prescott Park, the green space open to the public constrained to just 10-acres. A tremendous park in its own right, Prescott is just a taste of how Portsmouth could beneficially transform its waterfront.

The persona adopted by my Boston brethren is one of confidence and stubbornness, often bordering pomposity. It’s true that we generally fancy ourselves as authoritative figures of the New England realm, given the resources and luxuries afforded us back in Massachusetts.

Contrary to that, Portsmouth and its people are of a humble sort. They, too, have resources and luxuries at their fingertips: a thriving creative community, a tasty meld of classic and unconventional food and drink, proximity to nearby University of New Hampshire as well as Boston, and favorable livability.

However, when searching for New England retreats one is most likely to see ads for Boston, Portland, and other worthy sites in Vermont, Connecticut and Rhode Island as well.

Naturally, Portsmouth could benefit from an increase in exposure but it doesn’t need it and may not necessarily want it.

Though true-blue liberal and frequently ebbing to New Hampshire’s flow, Portsmouth exhibits an independent streak that rings true to the Granite State’s mantra of “live free.”

2 thoughts on “Portsmouth, N.H.: The Unpretentious Underdog of New England

  1. Lovely that you like our fair city, it is however, not without grievous problems.. Pay mind that this summer is the start of a four-year project on the waterfront, involving the rebuilding of the regional sewage treatment plant – long ignored by the city’s leaders, basically kicked ‘down the road’ since 1972 – it has come to the final end: the EPA is now thrown the gauntlet down.. Portsmouth HAS to bring the plant into modernity, and deal with the solid waste *properly*. Job MUST be done by 2020 or fines. Big fines. No excuses. As someone that lives on the street that will be carrying this traffic, I plan to get out of the city as much as possible – the stink alone of the trucks hauling the solids from the treatment plant as it is rebuilt is going to be horiffic.. Worse than low tide at the south millpond. (Which up until a few years ago has several antique houses with sewer mains that no one knew were still running into it, but everyone guessed, because it stunk like.. well, shit.)

    There will be, at peak, upwards of 100 construction trucks *a day* rumbling down to the bridge onto Pierce Island, which sits next to the Prescott Park and it’s summer theater.


    Fun times ahead as the tankers move the sewage out right past the tourists watching a summer play.


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