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New England by Heart

Portsmouth NH

Oracle House - Portsmouth NH

If you’re looking for a blend of history, culture, food, and natural beauty, your compass may be pointing towards Portsmouth, New Hampshire. This small, walkable city is nestled along the picturesque Piscataqua River as it widens into Portsmouth Harbor, wending its way around the many islands before emptying into the Atlantic Ocean.

Established in 1653, Portsmouth is one of the oldest cities in America and wears its history with pride. The rightfully lauded Strawbery Banke Museum, with its perfectly preserved houses from different eras, is a living testament to the city’s rich heritage. But history sprawls far beyond its borders, and walking along Portsmouth’s streets can make you almost forget that you’re in the 21st century. If you love historic house tours, your insatiable appetite might well meet its match in Portsmouth.

The original name of this area was Strawbery Banke, perhaps obviously for the wild strawberries growing on the banks of the river, but as we know, settlers in New England were very prone to naming places after the homeland, so it’s quite possible that it was named for an estate back in merry olde England. We may never know. In any case, New Englanders being pragmatic from the start, the name was changed in 1653 to Portsmouth. According to the petitioners pushing for the change, “Our port is as good as any in the land.” And indeed, Portsmouth became one of the most important ports in America.

Beyond history, Portsmouth is arguably one of the most robust arts destinations in New England, with world-class performances at The Music Hall and Prescott Park along with multiple galleries dotting the downtown.,\ The music culture dates back to 1630, just seven years after the first settlers. New arrivals were bringing more musical instruments than bibles. Unlike the Puritan and Separatists to the south, these folks were seeking land and wealth, not religious freedom. By the mid-1700s, Portsmouth had gained the reputation of a place of somewhat ill repute, and a magnet for traveling entertainers offering, let’s say, off color amusement.

When you’re tired of the arts (is anyone ever?), the foodie culture will entice you with top notch, diverse cuisine awaiting you in Market Square and beyond. After your gastronomic indulgences, spend some time walking it off with some excellent boutique shopping or a stroll through Prescott Park.

You can enjoy the best of Portsmouth in a weekend, but to fully experience this charming city, I would recommend 3-4 days, or a repeat visit. If you’ve got more time, you can branch out to places like Hampton Beach and Kittery, Maine.

Self-Guided Tours

About my self-guided tours

My Walk and Drive With Me tours are self-guided and designed to take no more than 2-3 hours. This allows you to easily incorporate them into an overall travel itinerary or simply enjoy one as a morning or afternoon excursion.

Walk With Me Tours

Portsmouth is a wonderful place for walking tours – it’s compact and full of history and eye candy everywhere you look. I include many, but not all, of the stops on the Black Heritage Trail, and I make note of them in my tours. There are plaques at those sites that provide historical information about Portsmouth’s unfortunate slave trade in its earlier era.

If this is your first time here, I recommend starting with the John Paul Jones & Governor Langdon and the Strawbery Banke and Prescott Park tours. The first will walk you past a number of historic sites, provide tours of two historic houses, and orient you to Market Square. The second will take you to Portsmouth’s most referenced attraction, Strawbery Banke. If you have time for one more, make it the Moffatts, Ladds & Warners tour, which finish out your orientation of downtown Portsmouth. From there, it’s up to you and your interests!

One other note – be sure to visit Candice Beaulieu’s The Historic New England Project website for great write-ups of houses on these tours along with others all over New England. As of this writing, she has covered the Rundlet-May House, the Jackson House and the Governor John Langdon House.

Drive With Me Tours

Other Excursions & Experiences

In Town

Market Square

Market Square

Market Square is the heart of Portsmouth. Anchored by North Church, it’s full of historical buildings mixed in with a plethora of boutique shops, eateries and watering holes, that extend down Congress and Market Streets. It’s a vibrant place where you can ramble for a few hours popping in and out of shops, take an ice cream or coffee break, or just sit and people watch.

Follow that with lunch or dinner and you have an excursion worth remembering.

USS Albacore

USS Albacore

If you don’t have “explore a submarine” on your bucket list, perhaps you should. And the USS Albacore will enable you to check that one off.

A research submarine designed by the US Navy to test experimental submarine features. It’s now open to the public and you can explore the spaces on your own while you listen to the audio recordings from former crew members that tell of adventures and daily life on the submarine.

There is also a nice little memorial garden here along with a gift shop where you can pick up a memento of your visit.

Music Hall

Music Hall

Opened in 1878 as a Vaudeville theater in Portsmouth’s more raucous days, The Music Hall has been entertaining audiences and enhancing the cultural scene in Portsmouth ever since. Saved from obscurity and the wrecking ball on more than one occasion, the plucky theater has held its own, evolving with the times and earning its permanent place in the heart of Portsmouth and its residents.

With many renovations and updates over the years, the theater now boasts two performing spaces, the Historic Theater and The Music Hall Lounge.

The Historic Theater is a feast for the eyes, with its fanciful proscenium arch and opera boxes, an elaborate domed ceiling with a crystal chandelier, and horseshoe balcony. The lobby is a marvel of imagination. In 2006, the cramped and outdated lobby was more than doubled in size by removing 700 cubic yards of ledge. It was then transformed into a “fantasy forest” of cast bronze trees, branches and vines, gilded Corinthian columns and elegant velvet settees.

Around the corner from the theater, is a 116-seat cabaret nightclub, renovated and renamed in 2022 to The Music Hall Lounge, previously the Loft. This is a more intimate space for smaller performances.

The Music Hall’s programming encompasses a wide variety of genres and artistic styles, showcasing both local talent and world-renowned artists. From music legends to emerging performers, from thought-provoking plays to captivating film screenings, the venue offers a diverse and enriching lineup of events throughout the year.


Rye NH

Portsmouth Harbor and Isles of Shoals

Portsmouth is at the mouth of the Piscataqua River, and with so much of its history tied to the water, it would be a shame not to get out on it. For a truly unique experience, consider sailing with the Gundalow Company for an afternoon or sunset outing in their authentic gundalow, the Piscataqua (of course), a traditional flat-bottomed river barge.

Another great way to get on the water is with one of the cruise companies. Portsmouth Harbor Cruises and Isles of Shoals Steamship Company provide narrated tours of Portsmouth harbor, the Isles of Shoals and the New Hampshire Seacoast. The isles themselves are part of Rye NH and Kittery ME, as the islands straddle the New Hampshire and Maine border.

Events not to Miss

Every town has some number of events throughout the year. Some have staying power, some don’t. Some are geared to special interests, like road races, while others appeal to a wide audience. Even some special interest events can become so iconic that they attract wide swaths of audiences and participants. My goal it to bring forth those events in a town (or nearby) that are enduring and treasured by the local community. For other events, be sure to check the local listings.

Market Square Day

Market Square Day

Kicked off in 1978, Market Square Day celebrates Portsmouth’s historic downtown with two performance stages and over 150 vendors. The event begins with a 10k road race followed by all day entertainment, food, crafts and merchandise. 

If you’re here for this event, it’s also a great time to explore the downtown area and all its historic buildings.

The downtown area is shut down to traffic for the June event and it’s estimated that over 50,000 people attend.

WOKQ Chowder Festival

WOKQ Chowder Festival

In June, it’s time to wake up the summer with the annual WOKQ Chowder Festival at Prescott Park. Local restaurants serve up their mouth-watering chowders in a bid to win your vote for the People’s Choice Award and compete for the judges’ Golden Ladle Award. And it’s not just about clams – entries include innovative recipes like Smoked Scallop Chowder and Spicy Seafood Chowder.

Along with the chowder, there are games, live music, children’s activities and ice cream (if you have any room left).

Seacoast Jazz Festival

Seacoast Jazz Festival at Prescott Park

Since 1983, the Seacoast Jazz Festival at Prescott Park has been delighting the community. Made possible through a partnership between Prescott Park Arts Festival and Seacoast Jazz Society, the festival was previously known as the Portsmouth Jazz Festival, then for 26 years as the Tommy Gallant Jazz Festival.

The August festival attracts local, regional and international talent and is held at Prescott Park along the Piscataqua River. As with all Prescott Park events, it is open to the public with a simple request for small donation. So bring your blanket and enjoy.

Notable Eateries & Watering Holes

I invite you to search for overall options and ratings on eateries and watering holes. My focus here is to point out those places that have historic or iconic value.

Library Restaurant

Library Restaurant

The Library Restaurant on State Street in Portsmouth was never a library. But its book lined mahogany walls and Shreve, Crump, and Low light fixtures have witnessed a lot of history. The restaurant space dates back to 1785, when it was the dining room of Judge Woodbury Langdon’s mansion, said Judge being the brother of the famous founding father John Langdon. George Washington and a string of presidents were guests of Langdon and the subsequent hotel that replaced his house in 1833.

The hotel – Rockingham House at that time – was acquired and expanded in 1870 by the intrepid Portsmouth mayor and brewer, Frank Jones, another figure that pops up regularly in Portsmouth’s history. His new and improved Rockingham Hotel was sadly destroyed by fire in 1884, leaving only the dining room intact. Mr. Jones, undeterred, rebuilt the hotel, sparing no expense and preserving the surviving dining room as the hotel’s banquet hall.

This is the building that still stands today. Luxurious spaces abound inside. Outside, the impressive brick facade sports two main entrances, above which two-story oriel window bays project outward on the third and fourth floors. Above those are the lofty busts of Langdon and Frank Jones set inside roofline pediments. Original and iconic cast iron golden lions from France guard the entrances.

The Rockingham Hotel was one of the finest north of Boston and remained a Portsmouth favorite until it was purchased by a developer in 1973 and converted into luxury condominiums. The restaurant reopened a couple years later as the Library Restaurant and has been serving upscale fare since.

So if it was never a library, why the name? Sadly, there’s no intriguing backstory – it’s simply a theme that blends nicely with its setting. One thing is for sure – this is the place to go to share a steak with the ghosts of legendary historical figures.

Ristorante Massimo

Ristorante Massimo

Massimo Morgia, born in Italy and raised in his first-generation family, opened Ristorante Massimo in 1994. The restaurant serves up authentic and upscale Italian fare in a sumptuous setting. Occupying the original 1816 custom house brick building at the corner of Daniel and Penhallow Streets, the restaurant boasts walls of brick and mahogany, exposed wooden beams and white cloth draped tables with gentle lighting. This creates a truly special atmosphere that does justice to the tantalizing cuisine.

A historic building and an amazing restaurant combine to make a memorable meal. It’s the go to restaurant in Portsmouth for special occasions and whenever you need that splurge of a truly great restaurant.

Portsmouth Book & Bar

Portsmouth Book & Bar

Portsmouth Book & Bar is a unique restaurant residing in the 1860 Custom House and Post Office at the corner of Pleasant and State Streets. Unlike the Library Restaurant, which isn’t really a library, the Book & Bar is actually a bookstore and a bar. It’s also a full service restaurant and live entertainment venue, but that would make for a very long moniker.

According to the website, there are more than 10,000 curated new and used books to be perused. Think Barnes & Noble on a smaller scale with great food, adult beverages and music, poetry readings, comedy and more. All set in an imposing granite building designed by Ammi Young (1798 – 1874), the first Supervising Architect of the U.S. Treasury Department, who designed many of the federal buildings across the U.S.

This building cries out for a little customs history. Prior to 1860, the customs offices resided at the 1817 brick building at the corner of Penhallow and Daniel Streets. That structure, with its distinctive curved Palladian window, housed shops on the first floor along with the post office, with the customs office on the second floor and the Atheneum and other offices on the third. The Atheneum, of course, later moved to its current building in Market Square. The 1817 building still stands today, housing shops and other businesses.

Traveling back even further, the customs office was a small attachment to the home of Joseph Whipple. Brother of Gen. William Whipple, a signer of the Declaration of Independence, Joseph was the customs collector for Portsmouth from 1786 to 1789. The U.S. Customs Service was founded in 1789, the same year George Washington visited Portsmouth, and Joseph became the very first customs officer in the U.S.

But back to the Book & Bar. While you won’t find a customs officer here, and your books will be free of taxes, the establishment will collect the NH meals tax on your food and beverage. After all, it would be kind of weird to be in a customs house without paying any taxes.

Portsmouth Brewery

Portsmouth Brewery

New Hampshire’s oldest brewpub, Portsmouth Brewery is the place to go to wind down a long day. With great food and handcrafted brews, highlighting locally sourced ingredients, this Market Street institution is a winner and easy to find – just look for those big mugs of beer tilting out from the brick exterior.

Portsmouth takes its breweries seriously – remember, this is the place of Stoodley’s and Pitt taverns where patriots raise mugs and voices in pursuit of independence. It’s where Frank Jones brewed the largest quantity of beer in America.

There are a number of craft brewers today in Portsmouth, and worth visiting. But the king is Portsmouth Brewery, evoking the public house of yore since 1991.


Geno’s Chowder and Sandwich Shop

Founded on Memorial Day in 1965 by local lobsterman Geno Marconi, the iconic Geno’s Chowder and Sandwich Shop is currently run by Geno and Evelyn’s daughter, Francesca. Located on the back channel of the Piscataqua River looking across to Peirce Island, the unassumingly picturesque eatery grounds the surrounding Colonial era homes to the river.

A local favorite, the casual dining spot specializes in classic New England style chowders and stews, lobster rolls and seafood dishes, served up on the deck overlooking the river. Local boats supply fresh lobsters across from the deck for the restaurant. That’s fresh.

Old Ferry Landing

Old Ferry Landing

So you’re in a historic small city at the mouth of a river emptying into the ocean in New England, and you can’t possibly do that without taking a meal at a seafood eatery on the water. Well, you’re in luck. How about an 1800s ferry terminal converted to a casual seafood restaurant run by three generations of the same family?

Could be good. Could be bad.

Fortunately, it’s good. Operating since 1975 by the Blalock family, Old Ferry Landing is a favorite of locals and visitors alike. So pull up a seat and order up a solid classic or modern seafood dish along with an excellent cocktail, and watch the tugboats come and go.

As they say on their website: Seafood. Drinks. Outside. On the water.

What more could you want?


Annabelle’s Ice Cream

You can’t miss Annabelle’s Ice Cream if you’re meandering down Ceres Street on the riverfront. That’s because there is a giant three dimensional ice cream cone hanging off the brick building. Unfair tactics – how can you pass up something like that? And you would be wise to give into the urge. With 30 flavors covering traditional and creative options loaded with the highest quality all natural ingredients, you’ll be glad you stopped.

Opened in 1982, it was purchased by 1992 by Dr. Lew Palosky and his late wife Linda. An optometrist with an office in the same building, Dr. Lew decided that the ice cream business was a more appealing career, and who could blame him? He was obviously right given the longevity of the shop.

Annabelle’s wholesales its product to restaurants, small businesses and boutiques, so if you find yourself enjoying some super-delicious ice cream, you might inquire if it’s from Annabelle’s.

Notable Lodgings

I invite you to search online for overall options and ratings on lodgings. My focus here is to point out those places that have historic or iconic value.

Wentworth by the Sea

Wentworth by the Sea

Wentworth by the Sea is a historic seaside resort hotel in New Castle. Built in 1874 on a bluff overlooking the Atlantic Ocean, it is one of the few remaining grand dames of the Gilded Age. You don’t need to stay here (yes, it’s pricey), but you will certainly want to park and wander the spaces, inside and out. Consider having lunch al fresco at Latitudes, so you can savor the setting. This is one beautiful hotel in a seaside setting that matches its grandeur.

From its founding in 1874, it has hosted numerous celebrities and dignitaries. U.S. President Chester A. Arthur was a frequent guest when he traveled from Washington to visit the Portsmouth Naval Shipyard. in 1905, the Russian and Japanese delegations met her for discussions on ending the Russo-Japanese War. Today, it’s not unusual to see a plethora of yachts docked at Wentworth’s marina.

Needless to say, the hotel offers a variety of amenities, including a spa, two pools, a fitness center, an 18-hole championship golf course, tennis courts, boating and more. With two restaurants and a pool-side bar, there’s not any particular reason to leave the resort, but of course you wouldn’t want to miss out on Portsmouth.

The Sailmaker's House

The Sailmaker’s House

The Sailmaker’s House is a circa 1800 Greek Revival home that was originally owned by John Holbrook, a sailmaker whose workshop was on the riverfront. Fully renovated in 2017, this 10-room inn boasts a lobby and lounge and all the feel of a historic house that’s been well updated. It’s also right downtown on a quiet side street, peaceful yet all of Portsmouth is right at the doorstep. 

The Hotel Portsmouth

The Hotel Portsmouth

The Hotel Portsmouth is a 19th century Queen Anne Victorian boutique hotel in the heart of downtown Portsmouth. Built in 1881 by John Sise, it was later occupied by his daughter and her husband, Alfred Gooding, a minister of South Church. A complete and careful renovation of the property was completed in 2014, leaving Portsmouth visitors with the experience of an appealing historic home with modern amenities. Your inn stay includes a gourmet continental breakfast.

Hotel Thaxter

Hotel Thaxter

Built in 1860, the brick and wood Hotel Thaxter was originally home to The First Congregational Church of Portsmouth and then the The Salvation Army before making its way into the lodging market. It’s named for Celia Thaxter, known for her cultivation of a multidisciplinary artist colony on the Isles of Shoals. 

The hotel has admirably added itself to the historic inns in downtown Portsmouth. Floor to ceiling windows on the first floor, a cozy lobby and parlor and luxuriously comfortable rooms expertly blend modern and historic elements. 

Conveniently located downtown across the street from Discover Portsmouth and the Portsmouth Historical Society, it’s the perfect launching point for exploring all that Portsmouth has to offer.

Ale House Inn

Ale House Inn

If staying in a 19th century brewery warehouse strikes your fancy, then Ale House Inn is the place to stay. The Portsmouth Brewing Company (not to be confused with the current Portsmouth Brewery) was the smallest of the city’s 19th century breweries. It didn’t survive Prohibition, but its warehouse did stand the test of time and now offers visitors a unique lodging opportunity.

While the rooms are modern, the gathering room at the inn boasts the old wood floors and brick walls, providing a sense of the original building. The inn is on Bow Street, steps from the riverfront shops and restaurants and a short walk to Market Square.

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