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New York City Road Trip to Portsmouth

A Guide To A Portsmouth Road Trip

Escape the oppressive New York City heat this summer to an unconventional seaside retreat. Portsmouth, New Hampshire, is just shy of five hours from NYC and its New England charm enchants visitors from near and far. Historic architecture, unique boutiques and innovative restaurants make this waterfront destination the ideal road trip this summer.

Fuel Up

Five hours is a long time to spend in the car, especially if you're bringing the little ones. Stop off in Springfield, Massachusetts, to stretch your legs and do a bit of sightseeing. Nestled along the eastern bank of the Connecticut River, Springfield has plenty to do for a few hours before getting back on the road. Hoops fans should check out the Naismith Memorial Basketball Hall of Fame (it's the building that looks like a spaceship; you can't miss it!), and youngsters will love The Amazing World of Dr. Seuss Museum. Take a riverside stroll through North Riverfront Park, weather permitting. 

Basketball | WhereTraveler
Basketball (©Ben Hershey)

Before hitting the road, grab a cup of coffee and a snack to keep you alert behind the wheel. There are several local cafes to choose from, but La Fiorentina Pastry Shop is the best in town. Since the end of WWII, La Fiorentina has been whipping up the butteriest pastries, cakes and the most crave-worthy cookies around. Dip a chocolate croissant in a hand-pulled espresso before heading farther north. 

Hot Espresso | WhereTraveler
Hot Espresso (©Tabitha Turner)


Welcome to Portsmouth, New Hampshire, a city where an astounding number of high-profile chefs have decided to open their passion projects. Take Chef Matt Louis, for instance! He's been named Food & Wine's best new chef and is a four-time James Beard Award nominee. His Portsmouth venture, Moxy, serves a delicious array of American tapas, including crispy Rhode Island calamari, pork belly bites and a verde fisherman's stew. 

If you're looking for incredible fare paired with out-of-this-world cocktails, The Wilder is where you need to go. Open for brunch, dinner, happy hour and late-night bites; this energetic eatery has the best back bar and cocktail menu in town. Order the "400 Rabbits" with mezcal and homemade carrot shrub or the espresso martini on nitro. Munch on the duck fat and white truffle popcorn while you peruse the menu for a salty snack. 


Take a tour of the Isles of Shoals (still veiled in mystery from the "Smuttynose" murders) as well as historic harbor tours of Portsmouth. Military and science buffs alike can squeeze down into the USS Albacore, a research submarine designed by the US Navy. Check out the control room, engineering spaces and bunkrooms on self-guided tours. Or, keep things very chill with a waterfront bench seat in Prescott Park with a used book from Portsmouth Book & Bar

Used Books | WhereTraveler
Used Books (©Tom Herman)


Whether you're looking for an opulent stay or just a place to rest your head, there are plenty of hotel options in Portsmouth, New Hampshire. From familiar national chains to historic boutique inns, there's a quiet space to relax that's just right for you.

Days Inn Kittery

85 US-1 BYP, Kittery, 207.493.2000

Ale House Inn

121 Bow St., Portsmouth, 603.431.7760

Sheraton Portsmouth Harborside Hotel

250 Market St., Portsmouth, 603.431.2300 

Ale House Inn Portsmouth | WhereTraveler
Hotel Interior (Courtesy Ale House Inn/Lark Hotels)