I’d start at Popovers on the Square, where breakfast feels like a fitting introduction to a New England weekend.

Their traditional New England popovers are served with maple butter. If you’ve never tried one, a popover has a golden exterior and a light, airy, hollow center. Pulling one apart and adding maple butter is a good reason to sit down and enjoy breakfast before the walking begins.

Popovers serves a variety of breakfast dishes, lunch options, and sweet bakery treats. That makes it a practical stop for a family: everyone can choose something that appeals to them, whether they want a meal or something from the bakery case. Its Market Square location puts you right in the downtown setting you’ve come to explore.

Coffee for the grown-ups, breakfast for everyone, and maybe a treat saved for later. That’s a promising start.

After breakfast, I’d head out without trying to turn the morning into a race between attractions.

Portsmouth’s downtown is a place to notice things: shop windows, historic buildings, little signs, and streets that invite you to see what’s around the next corner. Browse a few shops, pause wherever something catches your attention, and give yourself permission to wander.

With kids, I’d make this a shared adventure. Let each person choose a shop to peek into, or challenge everyone to find the most unusual item in a window. Older kids might enjoy browsing while you explore the same store; younger ones may do better with a short shopping stretch followed by an outdoor break.

You don’t need to buy something everywhere. The fun can be discovering a store you weren’t looking for or finding a small souvenir that reminds you of the weekend.

When everyone is ready for a change of pace, I’d make my way to Prescott Park.

Its waterfront setting, garden areas, and walkways give you a chance to slow down after a morning downtown. Spend some time watching the Piscataqua River, looking for boats, and enjoying the view.

In the warmer months, the gardens add seasonal color and the Arts Festival adds daily activities, concerts, and shows. At other times of year, the waterfront can carry the experience. I’d plan around the season rather than expect the same flower displays on every visit.

While you’re exploring, look for the love-lock fence along the waterfront near Memorial Bridge. The collection of padlocks makes an interesting little discovery, especially for kids who enjoy spotting details. Find an unusual lock or imagine the stories behind the names and initials—a small stop that can become part of your family’s memory of the weekend.

This is where I’d resist filling every minute. Sit for a while, take some photos, and decide together what comes next.

After lunch at one of the many amazing restaurants downtonw there are so many different things you can do.  Sailing with the Gundalow Company or visiting the Strawberry Banke Museum are my families favorites. 

If your family would love experiencing the waterfront from a boat, consider a sail with the Gundalow Company.

Their vessel, Piscataqua, is a recreation of the historic flat-bottomed sailing boats that once carried goods around the region. A public sail offers a different perspective on Portsmouth’s waterfront, and guests may be invited to help raise the sail or steer alongside the crew. For kids who enjoy boats or hands-on experiences, that could become the highlight of the trip.

Before planning your afternoon, check the Gundalow Company’s sailing times and ticket availability for your dates. Most public sails depart from and return to the Prescott Park dock, making this an easy activity to pair with your waterfront walk. Confirm the departure location for the specific sailing you choose.

For families who enjoy history, I’d consider Strawberry Banke Museum instead.

This living history museum preserves historic houses, gardens, and the stories of the Puddle Dock neighborhood. Its buildings help tell the story of how people lived and how the community changed over more than 350 years.

What interests me about adding it to a family itinerary is the opportunity to make history feel concrete. Instead of only reading dates, kids can think about the homes, work, and everyday lives of people who came before them.

A question like “What would you miss most if you lived here back then?” can start a better conversation than trying to remember every fact.

My Portsmouth footage includes only a quick glimpse of Strawbery Banke, rather than a full museum visit. If you’d like to explore inside, check the museum’s seasonal hours, ticket options, and available activities before you go.

I’d choose one main afternoon activity rather than try to fit in both. That leaves room for lunch, breaks, and the unexpected discoveries that make a weekend away feel special.

By dinner, I’d keep the decision simple.

Look at menus ahead of time and choose somewhere that fits your family’s tastes and budget. After a day of walking, this probably isn’t the moment to persuade a tired child to become an adventurous eater.

An earlier dinner leaves room for a final short walk or a return to the hotel. And if the family is done for the day, that’s fine too. Rest is part of a weekend away.  One thing I highly recommend in Portsmouth is reserving your table for dinner to avoid a long wait.  Portsmouth is a foodie destination, and though there are a lot of restaurants in the downtown area, they do get busy quickly.  

If you’ve chosen a hotel with a pool, this could be the time everyone has been waiting for. If you’re traveling with older kids, a relaxed meal with a waterfront view might be the better finish.

By Sunday morning, I’d let the family’s mood decide breakfast. Are you ready for coffee and a bagel before one last walk, or does everyone want to settle in for a bigger brunch?

The Green Room: Bagels, Smoothies & a Relaxed Start

For a casual breakfast, I’d consider The Green Room at Vaughan Mall. Its menu includes bagels, breakfast sandwiches, smoothies, and bowls—useful when one person wants something hearty and another would rather start with something lighter.

The greenery and wood-paneled interior bring a welcoming feel to the stop. Grab your coffee, let everyone choose breakfast, and spend a few minutes talking about the day before.

This would be my choice for a morning when we still want time to browse a few shops or return to the waterfront before heading home.

The Friendly Toast: Make Brunch Part of the Adventure

If breakfast is going to be the main event, I’d head to The Friendly Toast on Congress Street. Its colorful, quirky atmosphere and menu of pancakes, French toast, breakfast plates, and creative Benedicts make it an appealing option for a family brunch.

This is where I’d leave more time to settle in, study the menu, and enjoy one last meal together before the drive home. There’s room for someone who wants a classic egg breakfast and someone who considers French toast the proper way to end a vacation.

Weekend brunch can get busy, so check The Friendly Toast’s current hours and virtual waitlist before heading over.

Whichever you choose, ask everyone about their favorite moment of the weekend. The answer might be the boat ride, a shop-window discovery, or simply having time together without rushing to the next thing.

After a day of browsing shops, exploring the waterfront, and stopping for something delicious, having the right hotel to return to can make the weekend feel easier. My choice would depend on who’s coming along—and what makes a getaway special for your family.

With Older Kids: AC Hotel Portsmouth Downtown/Waterfront

I love the AC Hotel Portsmouth Downtown/Waterfront, especially for a trip with older kids who enjoy exploring downtown and sitting down for a meal with a view.

Rooftop at The Envio, above the hotel, brings something extra to the experience: a restaurant and bar overlooking the Piscataqua River and the bridges crossing it. It’s the kind of setting I’d choose for a relaxed meal after a day of wandering Portsmouth.

For a family weekend built around shopping, food, and waterfront walks, this would be high on my list. My video shows the hotel’s exterior and public spaces rather than a guest-room tour.

With Younger Kids: Hampton Inn & Suites Portsmouth Downtown

If your kids hear “hotel” and immediately ask, “Does it have a pool?” I’d look at Hampton Inn & Suites Portsmouth Downtown.

Its indoor saltwater pool gives younger kids something to look forward to after sightseeing—and gives you an option when the weather doesn’t cooperate. The hotel also includes a hot breakfast, which can make getting everyone fed and out the door a little simpler.

I’d leave space in the itinerary for swimming rather than squeeze it in at the end of an already exhausting day. Sometimes, the pool becomes the part of the trip the kids talk about most.