I loved visiting downtown Portsmouth, New Hampshire, and there are so many wonderful things to do in Portsmouth. On my road trip from Toronto to Maine, I made a point of stopping in as many lovely small towns as possible.
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I started in the larger city of Albany, New York, to discover the small town charms that lie within its quaint downtown neighborhoods. Next, I ventured to as many villages as possible in adorable Dutchess County.
Finally, I reached New England and stayed in Portsmouth, New Hampshire for an overnight stay. I recommend taking a full day to soak up the scenery and cute vibes of downtown Portsmouth NH. It’s a very walkable place, especially if you stay right in town. Leave the car behind and explore on your own two feet.
First things first: if you’re going to visit Portsmouth New Hampshire, you’d better learn how to say the name of the town. You don’t want to sound silly when you pronounce it completely wrong. So, how to pronounce Portsmouth? You don’t want to say Ports-MOUTH. It’s Ports-MUTH. Repeat after me, Ports-MUTH. Not mouth. Got it? Excellent!
Eat Breakfast at The Friendly Toast
Start the day off right with a hearty breakfast at The Friendly Toast. With a name like that, what’s not to love? Total disclaimer right here: I knew that I’d have a yummy breakfast at The Friendly Toast as I visited their location in Boston. This was on another road trip which included a day in Boston a couple of years ago. The Friendly Toast is a great spot for breakfast, lunch, and dinner in downtown Portsmouth NH. It’s also got such a wild and wacky interior design with decorations that you’ll just have to appreciate in person.
The Friendly Toast has a huge menu with breakfast choices to please everyone in the crowd. I really love their wide array of vegan breakfast items, as it can be difficult to find restaurants that serve vegan food for breakfast. Everything that’s vegetarian, vegan, or gluten-free is clearly noted on the menu. The Friendly Toast has all day breakfast, as well as lunch and dinner meals, too.
I’ll do you a quick favor and list all of their vegan menu selections, including what I ate for breakfast. There’s vegan nachos, a vegan breakfast burrito, vegan pancakes, vegan mac n cheese, the “in-taco-ble taco party” (Impossible burger with taco seasoning), the Impossible burger, the “Falafel Wraptor”, and the vegan Valhalla wrap. As you can see, there’s plenty to choose from. I went with the vegan pancakes with real maple syrup, which costs a couple of dollars extra. I’m Canadian, so I’ve gotta have the real maple syrup! I also ordered a side of tater tots with a cup of coffee.
Admire the Architecture of Downtown Portsmouth NH
Now that you’ve fueled up with breakfast, it’s time to go for a walk. Take the time to become acquainted with downtown Portsmouth NH. The entire downtown core is part of the Portsmouth Downtown Historic District, dating back to the 17th century. The architecture around town reflects over four centuries of history with five National Historic Landmarks and more than 1200 historically significant buildings. You’ll find downtown Portsmouth NH on the National Register of Historic Places.
The town was first settled in 1630 and was New Hampshire’s principal seaport for many years. You’ll see colonial era residences, old commercial buildings, and even a living, open-air history museum called Strawbery Banke. While I didn’t visit the Strawbery Banke museum, it’s worth checking out if you’re a fan of old homes and beautiful gardens.
I came across an interesting curved road called Bow Street. It’s one of Portsmouth’s oldest streets with a unique arched configuration. Before a disastrous fire in the early 1800s, there were many mansions lining Bow Street. Then, the street was rebuilt to house many small businesses, taverns, a blacksmith shop, boarding houses, and offices.
As you explore on foot, you’ll start to uncover some of the vibrant history of downtown Portsmouth NH. Take a stroll to admire the rows of brick buildings, brightly painted doors, and read the historical plaques in front of many old structures. For a more in depth look at the historical landmarks, parks, and gardens while getting some exercise with locals, check out this Portsmouth bike tour.
Discover the Street Art of Downtown Portsmouth NH
I really adore discovering a city’s street art. They usually come in the form of beautiful murals that bright up a place and can even tell a story about the people living there. There’s some delightful street art in downtown Portsmouth NH. You’ll just have to walk around town to take a look for yourself. Half of the fun of discovering street art is walking down back alleyways and the less traveled streets to find them.
The first one is a rather famous mural by marine life artist, Wyland. He started painting life size whales on the sides of buildings back in the 1980s to inspire thoughtful conversation about marine life conservation. There are 100 Whaling Wall murals in total around the world. In addition, Wyland painted on the lawn of the White House with 14,000 children to celebrate marine conservation with the President of the United States. While the Whaling Wall mural in Portsmouth is slowly decaying, it’s still a wonderful mural to visit.
As you continue your walk down Vaughan Mall, you’ll surely notice some interesting works of metal art. They definitely have a bit of a steampunk influence. Be sure to take a look at this interesting outdoor public art.
Next, head over to Ceres Street to discover the street art work, “Shark and Sea Bird”, by Shark Toof. It’s on the Granite State Minerals building and depicts a shark opening its mouth towards a window that has a sea bird sitting on top of it.
There are a few other colorful murals around town. Since half of the fun is in the discovery, I’ll let you walk around and find them on your own. They’re all located within the confines of downtown Portsmouth NH and shouldn’t be too difficult to find. The street art in the city is one of the best Portsmouth attractions.
Stop for Coffee at The Goods
Time for a coffee break! If you’re anything like me, you’re probably ready for a jolt of caffeine right about now. Head over to The Goods in downtown Portsmouth NH. It’s right around the corner from The Friendly Toast. Besides being a great place to get a fantastic cup of coffee, The Goods is also a market featuring fresh food that unites local farmers, craftspeople, and the community. Although I only stopped for some coffee (and to browse this cool little shop), there are also some vegan treats in their refrigerated case.
Visit the African Burying Ground Memorial
While Portsmouth can seem like a bit of a present day wonderland, it’s important to remember the dark history of the area. Everyone who visits Portsmouth, New Hampshire should spend some moments at the African Burying Ground Memorial. It’s right in downtown Portsmouth NH on Chestnut Street, between Court and State Street.
This memorial site is extremely important place that at one time was erased from history and existence. In the 1800s, this space was paved over and long forgotten. It wasn’t until 2003 when a work crew discovered wooden coffins and human remains that were determined to be of African descent. After much discussion, this memorial was erected in 2015 to restore this historically sensitive space as a sacred ground. It’s now a public cemetery, park, and site to memorialize the lives of the slaves buried there.
The African Burying Ground Memorial was created by the people of Portsmouth. As it reads on a plaque, “Those buried here are not part of black history or white history. This is our collective history.” The first enslaved man arrived in Portsmouth in 1645 from Guinea. Hundreds of people from Africa were forced into slavery in New Hampshire. In fact, as an affluent port town, Portsmouth had the largest population of slaves in the entire colony by 1767 (4% of the population). By 1810, there were very few slaves left in Portsmouth.
There were public records and documents referring to the “Negro Burying Yard” in Portsmouth where as many as 200 people were buried, starting as early as 1705. Even though their identities are not known, we’re encouraged to think of these people as individuals with their own stories. There are individual sculptures of people with messages written on them: “I stand for the Ancestors Here and Beyond”, “I stand for those who were taken from their loved ones”, “I stand for those who find dignity in these bones”. The African Burying Ground Memorial is a very powerful and meaningful place. I urge you to visit, read the signage and sculptures, and contemplate the events of the past and present.
Lunch at The Juicery
For a great lunch spot, I recommend stopping at The Juicery. After perhaps a heavier and unhealthy breakfast at The Friendly Toast, you might be craving something with loads of vitamins like a smoothie. I love ordering a smoothie that eats more like a meal: a smoothie bowl! The Juicery has delicious acai berry bowls with toppings like peanut butter, granola, banana, and more. In Maine, the same company owns the Maine Squeeze where you’ll find similar menu items – as featured in my vegan guide to Portland, Maine.
Go Shopping in Downtown Portsmouth NH
For those in search of a little retail therapy, one of the best things to do in Portsmouth is to go shopping. There are so many little boutique shops in downtown Portsmouth NH. You’ll find clothing shops with both new and vintage styles. There are jewelry stores, craft and hobby shops, gift shops, antiques, bookshops, home furnishing stores, and so much more. I saw plenty of stores selling items unique to New England to remember your holiday there. You never know what you might find when you go shopping in Portsmouth New Hampshire.
Take a Stroll at the Parks of Downtown Portsmouth NH
There are a couple of really lovely parks that you can reach from downtown Portsmouth NH. You can easily walk between them both as well, though there is ample parking at both parks. If you’re looking for those famous seaside views of New England, you won’t want to miss a stroll through the park.
Prescott Park is a 10 acre waterfront park along the Piscataqua River in the heart of downtown Portsmouth NH. It used to be a run down, industrial area until two wealthy sisters purchased the land and donated it to the city in 1940. The space became a public park, free and accessible to all. Since the 70s, there are local theater productions of Broadway plays at the park, outdoors during the summer months. When you walk around, you’ll notice a fence of love locks, as well as a really intriguing whale statue.
Peirce Island and Four Tree Island
Only a short walk from Prescott Park lies Peirce Island and neighboring Four Tree Island. A bridge from downtown Portsmouth NH connects the mainland to Peirce Island, and you can walk across to the smaller Four Tree Island from Peirce Island. There are many beautiful walking paths and wonderful views of the river. It’s a very peaceful spot in the city. Both parks are on my list of the best Portsmouth attractions for nature lovers.
Dinner at Green Elephant Vegetarian Bistro
Lucky me – I had the chance to dine at the Green Elephant Vegetarian Bistro in both Portsmouth and Portland, Maine! If you’re vegan, vegetarian, or love plant-based meals, you simply must dine at the Green Elephant Vegetarian Bistro. I ordered a noodle dish with loads of veggies and soy meat that was very yummy.
Enjoy a Pint at the Portsmouth Brewery
If you’re still looking for what to do in Portsmouth NH, stop by the Portsmouth Brewery after dinner for a pint of locally produced craft beer. I didn’t have the chance to sample beer from the Portsmouth Brewery on my trip. It’s on my list of things to do in Portsmouth NH on my next visit. The Portsmouth Brewery is open until late, making it the perfect evening hang out spot.
Map of Downtown Portsmouth NH
Here’s a handy map with everywhere that I’ve mentioned listed on it. You can use it to find your way around town or any Portland attractions that you’re seeking. There are many things to do in Portsmouth NH on this map.
From downtown Portsmouth NH, I continued on towards Portland, Maine and picturesque southern Maine. On my way home, I spent a day in Hudson, New York to continue the cute, small town America theme. Road trips around the USA are among the best ways to visit the villages and towns. A road trip to New England is an amazing adventure, and you’ll find that it’s not very touristy or busy in the spring.
Where to Stay in Portsmouth New Hampshire
My top choice for where to stay in Portsmouth New Hampshire is The Sailmaker’s House. It’s right in the middle of downtown Portsmouth NH, so you can walk everywhere right from your accommodation. This is a historic home, originally owned by the sailmaker, Thomas Pierce. Later, the property eventually became an inn, and today it is a charming hotel.
The Sailmaker’s House is a self catering accommodation where you’ll be provided with a key code. This provides access to the front door and your guestroom. I stayed in a room on the first floor, right outside of the coffee/tea/snacks table. Yes, there’s a table full of delicious treats and warm beverages available 24/7.
While there won’t be a breakfast in the morning at this hotel, there are always snacks out in the common area. There’s also complimentary Wi-Fi throughout the hotel, and a couple of comfy common areas if you’d like to meet with your friends and family outside of your guestroom.
There is a parking lot attached to The Sailmaker’s House that fits 9 cars: first come, first serve. I didn’t have any issues finding a parking spot. It was very convenient to be able to leave my car and walk all over town.
I highly recommend staying at The Sailmaker’s House. It’s a unique accommodation in a historic home, but has a comfortable and modern flair. You’ll have everything for a restful night’s sleep, and I wouldn’t hesitate to stay here again. Book your stay at The Sailmaker’s House and feel free to check out more reviews by fellow travelers.
Looking for more choices? There are lots of hotels in Portsmouth and Airbnb accommodations to check out. Here’s a handy booking tool where you can see all of the Booking.com accommodations and Airbnbs in one place. It’s easy to compare prices and find the best rate.