I wanted to go to Portsmouth because I'd once heard it compared to New London. (See also: New Bedford, Newburyport.)
I said that to a friend of mine who'd been to Portsmouth a few times and she replied "Portsmouth is New London if New London got its [expletive deleted] together."
In fact, the comparison I was thinking of had not been intended to imply the two cities were exactly alike (although they both have submarines, Wyland whale murals, history, and numerous coffee shops.) It was only a reference to some specific improvement that Portsmouth had made to its waterfront or traffic patterns or zoning laws which the speaker, an expert in city planning, thought New London would do well to emulate.
Now that I've been to Portsmouth, I can say that it is not like New London. Yes, both are walkable old seaport cities with interesting architecture and many restaurants. But New London is decidedly eclectic, multicultural, and, though I think I might hate this word, gritty. Portsmouth, at least when I was there, seems to be populated almost entirely by catalog-attractive affluent white people wearing Lululemon. (And I don't think anyone who loves New London, as I do, would wish that fate upon it.) New London is also much smaller, with a larger population.
City planning ideas aside, the only important thing the two places have in common is they should both be included on all must-visit lists of New England.
Seriously, if you've never been to Portsmouth, just go. It's the sort of town you'll want to return to before you've even left. And you might want to convince someone else to come with you. That way, when you point at a perfect brick building or some adorable item in one of the multitude of little shops downtown and say "Look at thaaaaat!" you'll appear less crazy.
Shopping:
Pickwicks Mercantile
Scallops Mineral & Shell Emporium
Sheafe Street Books
Riverrun Books
Portsmouth Book & Bar
To see:
Wyland Mural (Off Vaughan Mall)
Oracle House (One of the oldest houses in New England, Marcy Street and Court Street)
Temple Israel (New Hampshire's first permanent synagogue, 200 State Street)
Portsmouth Atheneum (9 Market Square)
Prescott Park (Marcy Street)
Commercial Alley (Between Market and Penhallow Streets)
What I'd do next time:
Strawbery Banke Museum
Fort Constitution and Portsmouth Harbor Lighthouse, New Castle
I became stranded in Portsmouth years ago when my car broke down there late one winter night, necessitating spending several chilly hours in a sleeping bag. Early the next morning, I stumbled into the Breaking New Grounds coffee shop (which still exists, but in a different, larger space) first thing to warm up and was swept up in a wave of kindness. The staff and their friends drew my predicament out of me in conversation after I handed over my iced travel mug for refill. They saw to it that I had a warm place to stay the next night and the advice of their mechanic friend to enable me to fix the car in a parking lot. To this day, it remains my go-to reminder and standard of kindness to strangers. It's still a fine place to visit.
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