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The Weekender: Portsmouth, New Hampshire

A gastronome’s guide to the third oldest city in the country

Portsmouth, New Hampshire is one of those small, special places not to be overlooked by travelers drawn to the charms of New England. The country’s third oldest city boasts the best of everything, from exceptional food and drink and coastal sightseeing (all walkable for those who prefer to explore on foot) to idyllic local winery tours expertly showcasing East Coast terroir. It’s a destination that seems to maximize big city offerings within its small town confines, and if you’re someone who appreciates a great dish or drink against a picturesque coastline, this is the place for you. Below you’ll find our ideal 72-hour itinerary for exploring Portsmouth.

Friday Afternoon:

Arrive to Portsmouth and check in at The Port Inn. Settle into your King Suite, a cozy yet spacious room in the main building complete with a plush bed and a wet bar. You won’t be spending too much time in your room, but it’s a lovely place to come back to after a day of (spoiler alert) exploring downtown and its nearby wineries.

The Port Inn

The Port Inn

Friday Evening:

After decompressing for a bit following your earlier travels, hop in your car or cab and head for the downtown area (just minutes from your hotel). Split your evening between Raleigh, a quaint natural wine and beer bar showcasing local ingredients, and The Wilder, a modern gastropub with a cocktail program worth checking out during your visit. Grab a round of drinks and a few bites at both before heading back to your hotel for the night.

Saturday Morning:

Wake at your leisure and make the quick drive back to the downtown area for breakfast at La Maison Navarre, where classic crêpes, croque monsieurs, and coffees await. From there, take a leisurely stroll around downtown to check out the shops and scenery before your tasting at Flag Hill in Lee. If you have time, savor an light bite or drink on the deck overlooking the water.

Saturday Afternoon:

Drive to Flag Hill, an award-winning distillery and winery located just 30 minutes outside of downtown Portsmouth. Here, wife-and-husband team Maddie and Brian Ferguson oversee an impressive operation producing an extensive line of spirits alongside a collection of wines backed by the team’s scientific approach designed to flawlessly showcase the local terroir. For tour options, check out the property’s events calendar before your visit.

Saturday Evening:

After your tour and tasting at Flag Hill, return to your hotel for a few moments to yourself before dinner. Once you’ve recharged, make your way to the Portsmouth Brewery, a beloved local pub known for its local brews and approachable fare–this convivial spot is a must-do while in town, and its rotating menu of beers is not to be missed.

From there, walk approximately five minutes over to Row 34, where raw bar offerings and craft cocktails reign supreme, making for a perfect way to end your last evening in Portsmouth. Grab a seat at the bar and opt for the bartender’s choice oysters and a glass of something sparkling to wash it down.

Sunday Morning:

Depart for home after a quick, casual breakfast at The Friendly Toast, a local all-day favorite featuring an extensive menu with vegan and gluten free options sprinkled throughout. There’s fuel here for everyone for the way back.

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