How to Plan the Perfect Fall Day Trip to Portsmouth

You can spend a day in Portsmouth touring the town’s historical homes, people-watching on Market Square, and experiencing living history at the Strawbery Banke Museum.

The city is made for self-guided walking tours thanks to a very ped-friendly downtown.

How you spend your day can depend a bit on when you visit, though. My tips will reflect our trip in the fall. You’ll experience fewer crowds than in the summer months while enjoying some pretty tremendous fall foliage.

Just note that you may miss out on some of the summer festivals and other events that happen in the warmer months if you time your visit for the autumn. You can’t have it all, but you can get close.

Nosh on breakfast in Portsmouth.

My mom always says that breakfast is the most important meal of the day. In my normal life, I usually skip it to spite her (and because I don’t wake up hungry), but vacations hit differently. Here are a few top spots for breakfast in Portsmouth:

• The Goods: The focus is on fresh at this local favorite. Everything you munch on at The Goods is sourced from farmers in the surrounding region. That also means you never know what to expect at this one, but you know it’ll be fresh.
• La Maison Navarre: Pretend like you’re French and fancy at this cafe. Nibble on a quiche or any of their pastries. Are macarons appropriate for breakfast? I digress. They have a variety of both sweet and savory crêpes, too.
• The Friendly Toast: If you’re traveling with kids or want all of the whimsical colors for the ‘gram, The Friendly Toast is a popular option for its colorful interior. It’s a chain, but it’s limited to locations in New England.

Tour Portsmouth’s historical homes.

Portsmouth is one of four original towns in New Hampshire, the second oldest city in the state, and per Britannica, the oldest settlement in New Hampshire. 

That’s a lot of facts to take to your next trivia night. 

It’s a popular New Hampshire travel destination for anyone interested in historical architecture, and you’ll have quite a few historical homes to choose from if this is your angle. Here are a few of the most popular historic homes in Portsmouth:

• Moffatt-Ladd House & Garden: This National Historic Landmark was once the home of William Whipple, a Revolutionary War general and a signer of the Declaration of Independence.
• Governor John Langdon House: This one, also known as the Governor John Langdon Mansion, was built for, you guessed it, John Langdon. Langdon was a general in the American Revolutionary War and a signer of the U.S. Constitution.
• The Warner House: The Warner House (previously known as the MacPheadris–Warner House) is one of the oldest brick structures in New England. Visit to see how it’s changed since it was built for Captain Archibald Macpheadris in the 1700s.
• The John Paul Jones House: This historic home is run by the Portsmouth Historical Society and named after Jones, a Scottish sailor who fought in the American Revolution. Rumor has it that he rented a room in the house in 1777.
• Jackson House: If you’re already visiting the USS Albacore Museum, this one is an easy add-on before or after your submarine tour. This National Historic Landmark is the oldest wood-frame house in the state.
• Wentworth-Coolidge Mansion: This 40-room home on the Little Harbor was the working residence of Benning Wentworth, the state’s first royal governor. Walk a waterside path that connects the site with surrounding conservation land.

People-watch on Market Square.

Take some time to linger in the heart of Portsmouth if you’d like to explore the shops, galleries, and cafes. This is downtown Portsmouth’s small business hub. If you’re visiting in the fall as we did, expect all kinds of pumpkin fun.

Note: I’m really not into suggestions like “Go shopping!” but Market Square is worth a visit for the people-watching alone. If you are into shopping, Bliss and The Drift Collective appear to be two nice shops with unique items for you to bring back home. 

Experience living history at the Strawbery Banke Museum.

Whether you’re traveling with the family or just love tourist attractions that educate while they entertain, you won’t want to miss the Strawbery Banke Museum. This living history museum depicts life in Portsmouth from the late 1600s until the 1950s.

There’s certainly a focus on colonial life, but one of the exhibits depicts the lives of the Abenaki, the indigenous people who were here when the settlers arrived. Don’t miss it if you want the full picture.

Fun fact: No, you won’t be learning much about strawberries here. The early settlers built their homes on what they called Strawbery Bank — I suppose they couldn’t spell back then — after the wild strawberries growing OR after an English estate. The history’s vague.

The guides here are very into role-playing, so feel free to interact with them as you move through the indoor and outdoor spaces. Admission tickets are available online and are good for two consecutive days if you’d like to spread out your visit. 

This attraction is closed in the winter months, but you can still take the kids ice skating at the Labrie Family Skate on Puddle Duck Pond if that strikes your fancy.

Relax at Prescott Park.

Prescott Park is a lovely place for a stroll along the Piscataqua River. There are 10 acres to explore here, so find your little slice of paradise and pop a squat for a while. Enjoy the sculptures, water features, and public gardens along the way.

The park is also home to the Prescott Park Arts Festival, a full roster of seasonal concerts, outdoor movies, and other special events. 

You won’t the events in the fall, but there are different festivals in the park during the autumn months. Check out their schedule before your visit in case it coincides with a special event.

READ MORE: If you’re on a road trip, use my New England road trip guide to plan your travel to destinations less traveled.

Tour the USS Albacore Museum.

This retired research submarine comes to us courtesy of the U.S. Navy. It’s worth a visit if you’re really into subs, as you’ll get to see how they tested features seen on modern subs.

You’ll also get a taste of life under the sea without any singing crustaceans judging your life choices.

Tours of the USS Albacore are self-guided. Buy tickets upon arrival. If you’re on your map apps, note that this one may be listed as the USS Albacore Submarine and Museum.

Have a pint at Portsmouth breweries.

The Portsmouth Brewery has been killing it in Portsmouth since 1991. That doesn’t just make it special to Portsmouth. This is New Hampshire’s original craft brewery. You can eat at the brewery or have a beer or two and continue on to eateries nearby.

At the very least, have some sips of what they have on tap during your visit. We were there in the fall, so had to get in on that coffee milk stout.

Are breweries your jam? There are a few others to choose from. Here are more of my top picks for breweries in Portsmouth:

• Cisco Brewers: Cisco has a few New England locations if you’re in the area for a while. In Portsmouth, enjoy a variety of small-batch beers and sandwiches.
• Earth Eagle Brewings: This one has a lively outdoor space, a variety of beer styles on tap, and an impressive burger and hot dog menu if you want a nosh.
• Great Rhythm Brewing Company: Bring your pals to their outdoor space over North Mill Pond. If it’s a chilly day, their tasting room is just as fun.

Sip on a glass of wine, instead.

If you want wine over beer, visit Corks & Curds. They also have 75 kinds of cheese for you to peruse. Is that too many? It’s not if your mouth is watering at the thought like my own. Their marketing is on point, too.

Eat at the best restaurants in Portsmouth.

Portsmouth is a foodie town. It boasts a vibrant culinary scene with diverse dining options, from seafood shacks to upscale restaurants. The city’s commitment to farm-to-table cuisine, fresh seafood, and craft beverages makes it a haven for foodies.

Any of the options below are great for a midday meal or dinner while in Portsmouth. Check hours before you head out, as some are open later than others:

• Black Trumpet: If you’re celebrating a special occasion, look no further than this romantic spot. Spicy squid, mussels, and house dumplings all sound pretty sexy to me.
• Fezziwig’s Food & Fountain: Dine on salads, sandwiches, and crêpes at this charming brasserie. Leave room for one of their milkshakes if you’re nursing a sweet tooth.
• Moxy: This eatery isn’t just vibes. It’s accolades, too. Taste why with anything on their shareable tapas menu, like mini beef burgers, fried pickle chips, and crispy pork belly. 
• Old Ferry Landing: Oh, you’re here for lobster rolls? I’ve got you with this seafood shack. They also have chowder, which you can have any time, and a variety of grilled fish options if you’re here for your health. Good for you, friend.
• Popovers on the Square: If you want to get mobile with your lunch and snack on a classic New England pastry, pick up a bag of popovers. They serve up a light lunch, too, if you don’t feel like popovers.

If you have room for dessert or believe it’s a different stomach completely, head to Kilwins for hand-crafted chocolates, delightful confections, and small-batch ice cream.

They’ve been at it since 1947, so you can trust that they know what they’re doing when it comes to taking care of your sweet tooth. If you’re here in the fall, their caramel apples are a big deal in these parts.

Walk to Maine at Memorial Bridge.

This truss bridge isn’t really something to “do,” per say, but more something to be aware of in case you’re there to catch the bridge lifting. If you want to walk to nearby Maine, you can do that here, too. Badger’s Island in Kittery is on the other side of the bridge. 

Fun fact: We took the quick stroll just to be all, “We walked all the way from New Hampshire!” once we got there. We’re nerds.

There are a few decent eateries on Badger’s Island if you’d like to stick around. Badger’s Island Pizza serves up New England-style pan slices. Ore Nell’s Barbecue dishes out Texas-style meats and hospitality. 

I’m not sure it’s the best of Maine, but it’ll do if you want the experience on the other side.

With More Time in Portsmouth

If you’re in Portsmouth for a bit longer, there’s plenty to do to fill up more time. Check out more things to see in Portsmouth that are still on our list for repeat visits:

• Visit the historic Portsmouth Harbor Lighthouse, New Hampshire’s only deep-water port.
• Walk the Black Heritage Trail through the African American Historical Society of Portsmouth and see the African Burying Ground.
• Catch a music, theater, or comedy show at The Music Hall, a historical venue.
• Plan some live theater while you’re at it at the Seacoast Repertory Theatre.
• Take a quick trip to Peirce Island, a 27-acre island that’s home to a 1930s-era outdoor pool and boat launch.
• Visit the Portsmouth Athenaeum, a membership library and home to the Randall Gallery and regular cultural events.
• For more art on a rainy day, try out the Museum of New Art (MONA) Portsmouth and its ever-changing contemporary exhibits.
• Connect to Four Tree Island, an island that isn’t even technically an island and most definitely has more than the described number of trees.
• Take a haunted walking tour of Portsmouth’s best spooky sights.
• Bring the kids to Water Country Water Park, a seasonal park with slides for family fun and big kids, too.
• Go on a Portsmouth scavenger hunt for intriguing historical spots and hidden gems.

Where to Stay in Portsmouth

If you’re not visiting on a day trip to Portsmouth, you have a variety of hotels at your disposal for an overnight.

We’ve stayed at the Ale House Inn, a historic property that once housed a brewery. Prices for this one get high in the summertime, but if you’re here in the off-season you can nab some good deals.

Check out the map below for more options:

I’d love to linger in Portsmouth.

People visit Portsmouth because it’s such an easy day trip from popular big cities nearby, like Boston. It’s also a destination all on its own thanks to its scenery, history, and cultural offerings. 

I’d love to return and linger for longer than one day in this charming town, as I bet it’s one of those places that reward slower travel.