Portsmouth in 48 Hours

Photo by Bart Beeson

A weekend of fun and food in Portsmouth with a little history thrown in

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Get ready for a weekend in Portsmouth – with some great food and cold drinks, some time on the water, and even a little history thrown in. And you can leave your car keys at the hotel – for this weekend itinerary, all your activities are within walking distance (so if you feel like ordering one more drink – go for it!)

Friday Night in Portsmouth

On Friday night head for dinner at the Clipper Tavern, which has a selection of creative sliders as well as some tasty seafood dishes and a good beer selection. If you’re not too tired after dinner, head over to the Rusty Hammer for a night cap. This recently revamped addition to the Portsmouth scene is popular with locals — if you go more than a few times the bartender might pour you your drink before you sit down. They have 32 beers on tap and make a mean Moscow mule.

Saturday in Portsmouth

Start your Saturday off with a hearty breakfast at The Friendly Toast. This Portsmouth institution has a kitschy, eclectic décor and a huge menu – offering a lot more than just toast. You can order breakfast food at any time and anything from the menu can be made vegetarian.

After breakfast head off to explore downtown Portsmouth. You can easily spend a couple hours here, doing some window (or actual) shopping, strolling the cobblestone streets, and checking out the historic houses. Make sure to walk through Prescott Park, a beautiful park right on the water, and stop by Point of Graves Burial Ground, one of the oldest cemeteries in the U.S., with gravestones dating back to the 1600s. And for an interactive history experience – head over to Strawbery Banke, a living museum whose costumed, role-playing staff will give you tours of the historic houses and gardens on the 10-acre property.

You’ve probably worked up an appetite by now, so head over to “the decks” – a string of waterside restaurants with outdoor seating. Grab a table at the Old Ferry Landing, and try their fried scallops and a local Smuttynose beer, or their Jimmy Juice, a rum-punch specialty.

When you’re done with lunch, stroll back through Prescott Park and over the bridge to Four Tree Island, a spit of land off of Pierce Island. There are picnic tables and benches if you want to rest, and great views of Portsmouth and the Naval Shipyard.

After heading back to your hotel for a change and maybe a rest (especially if you tried the Jimmy Juice) it’s time to head out for Saturday night in Portsmouth. For dinner, try Moxy, a trendy restaurant serving tapas and small plates. Both the Portsmouth rarebit and the lacquered pork belly bites are delicious. For an after dinner drink, head to the Press Room, a fun bar with a great beer selection that often hosts live music. If you’re still hungry, stop off at Gilly’s – a converted old train car that’s popular for its late night eats – you can’t go wrong with the cheese fries.

Sunday in Portsmouth

For Sunday brunch head to Street — serving international street food, it’s about a 15 minute walk from downtown (or an easy drive). There will probably be a wait on nice weekends but it’s a fun scene and the food is worth it, plus they serve the best Bloody Mary in town while you wait.

For one last afternoon activity, get your sea legs on a narrated cruise of the Portsmouth Harbor and out to the Isles of Shoals, taking in the scenery while learning about the fascinating history of these islands. Depending on how much time you have, you can spend the day on Star Island and take a walking tour. It’s a great way to cap off your weekend in Portsmouth before heading home.

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