Just across the Elizabeth River from Norfolk, you’ll discover the historical waterfront port of Portsmouth, where the past and present collide, making it the perfect destination for travelers of all ages. In this post we’ll dive into Portsmouth History before checking out a few Must-See destinations in the area.
Portsmouth’s location on the Elizabeth River, not far from the Chesapeake Bay has long made it a prime port. The area was first explored by the English in 1608, when Jamestown colonist John Smith visited the area. In 1620, Jamestown’s John Wood saw the site’s potential as a ship building location. The early colonists lived in plantations along the Elizabeth River, before the town of Portsmouth was officially founded in 1752 by William Crawford on 65 acres carved from his riverfront plantation. Crawford was a wealthy merchant and ship owner who at various times had served in public office from Norfolk County presiding judge to high sheriff, militia lieutenant colonel and representative to the House of Burgesses. The city is named for the English port of Portsmouth, a hope at the time this port would rise to importance in trade and shipbuilding like its English namesake.
*Interesting history: William Crawford received a portion of his property from what was once land owned by early settler William Carver who was a rebel in the Bacon’s Rebellion plot. Bacon’s Rebellion was squashed after their belligerent leader died. We learned about this history when we visited Bacon’s Castle last year.
A History of Shipbuilding…
Portsmouth’s shipbuilding legacy took sail when in 1767, shipbuilder Andrew Sprowle founded the Gosport Shipyard adjacent to Portsmouth, ushering in a new era of ship building for Portsmouth.
Andrew Sprowle, a Scotsman loyal to the Crown and his fellow Scot, Virginian Lord Dunmore, exemplifies the initial hesitation many Scotsmen felt about raising arms against the British. They remembered their losses at the Battle of Culloden. This mentality did begin to shift, however, as the war waged on and the advantages of an independent America became clearer.
When Dunmore was driven out of Williamsburg, he set up his base at Gosport’s shipbuilding center, a hub of activity near Portsmouth and Norfolk. Dunmore promised freedom to any enslaved persons who would fight with the Loyalists, forming his Ethiopian Regiment. While this sounded promising, historical study reveals this freedom came at a great cost, with many soldiers dying from smallpox or never fully securing their promised liberty.
On the patriot side, African Americans also fought, including revolutionary hero William “Billy” Flora, a free Black Portsmouth entrepreneur and the “Hero of the Battle of Great Bridge.” There is a statue dedicated to Billy in Portsmouth, paying homage to his role in the Revolutionary War
The slaughter of British troops at that short, pivotal battle led to Virginia’s last Royal Governor being driven from his post. The Ethiopian Regiment, fleeing with Dunmore, was decimated by smallpox at Gwynn’s Island, never fully enjoying their promised freedom. Still, Dunmore’s decree continued to draw the enslaved, and at the War’s end, ships leaving Portsmouth carried countless once-enslaved British soldiers to a life of freedom in Nova Scotia.
With the changing tide created by the Battle of Great Bridge, Portsmouth soon became a patriot stronghold. Its crucial role in Virginia’s break with colonial rule marked the beginning of its strategic importance throughout the War for Independence.
Revolutionary Portsmouth:
After Norfolk was burned on January 1st 1776 and essentially reduced to ash, Portsmouth became the center of commerce on the Elizabeth River. However as the war continued on, Portsmouth also faced similar threats as Norfolk. In 1779, the British stormed the area, destroying the nearby Fort Nelson (built to defend the area in 1776). The patriots did not want the British to have control of the shipyard, so they were forced to burn it before retreating.
In 1779, George Washington granted enslaved men freedom in exchange for service in the Continental Army. The American Battlefield Trust has an excellent article about African Americans in the Continental Army, which became most integrated, but freedom was still a hope that wouldn’t be fully realized for most enslaved until after the American Civil War.
One of the scariest events for Virginia during the American Revolution was when the turncoat traitor Benedict Arnold marched on Portsmouth in support of his now British allegiance. They occupied the area for seven long months, burning area crops and causing chaos in the area. I lost any potential sympathy (not that I can much to begin with) for Arnold’s decision to turn after reading about his time in Virginia.
During Arnold’s occupation with The British, a true Revolutionary Spy novel emerges. Enslaved Patriot hero James Fayette operated as a Patriot double agent in the area, infiltrating Arnold’s and then Cornwallis’ headquarters. Fayette’s intel was instrumental in the British defeat at Yorktown. He eventually earned his freedom in 1787 after petitioning The General Assembly. He took the name of the Marquis de Lafayette who fought for James’ freedom. Fayette worked with Lafayette during his time as a spy. You can read more about this amazing American hero here.
After The Revolutionary War
After the American Revolution, Portsmouth continued to grow as a shipbuilding center with the Gosport Shipyard eventually being sold to the Federal Government in 1794. Today it is still in operation as the Norfolk Naval Shipyard – still owned by the Federal Government and U.S. Navy!
It was the site of a Yellow River outbreak in 1855, which led to a typically shutting down of the city and significant deaths. You can learn about the epidemic and pay your respects to those who bravely fought against the epidemic and died in the outbreak at the Laurel Hills Cemetery Yellow Fever Memorial. It is a somber but important piece of Portsmouth’s history. Interesting enough a pioneer in stopping Yellow Fever, Walter Reed, was from Gloucester Virginia, which is on another section of the Chesapeake Bay across the bridge from Yorktown (stay tuned for a Gloucester adventure soon)
During the Civil War, Portsmouth was initially under the Confederacy before Union troops took over in 1862. Civil War history can be found throughout the city as you meander through Portsmouth historic neighborhoods. Discover more Portsmouth history here.
Must See in Portsmouth:
I recommend starting your Portsmouth visit with a stop by the Visitor’s Center on High Street. The knowledgeable staff can help with maps, tourist info and recommendations for where to eat. Learn more here
Walking through History:
Portsmouth is a highly walkable community allowing you to explore a lot of the heritage and cultural sites on foot, all while taking in delicious food and spirits and perusing local shops.
The city of Portsmouth has a great guide to various walking itineraries on their official tourism page. From the Underground Railroad Tour to History Alive (with famous spy James Fayette as your guide) adventure is only a step away in Portsmouth – Walking Tours in Portsmouth
Explore Portsmouth’s Olde Towne:
Experience the heartbeat of Portsmouth’s history as you stroll the streets of Olde Towne. Located along the city’s famous waterfront Seawall, you’ll discover tons of fun things to do in this vibrant section of Portsmouth. Olde Towne boasts the largest collection of period homes between Charleston, South Carolina and Alexandria Virginia. This section is home to the oldest operating Naval Hospital and the Gosport Shipyard – first operational dry dock in the US. You can take in the quaint charm of historic houses and stunning architecture, while also immersing yourself in the vibrant neighborhoods, delicious restaurants, cool antique shops and family fun. This guide gives you the scoop of Historical sites in Olde Towne: Website
The Portsmouth Seawall is a must while in Portsmouth, this 1.5 mile riverfront walk provides scenery with lots of history along the way. For a self-guided walking tour of The Portsmouth Seawall click here
Olde Towne is home to several amazing museums including:
Jewish Museum and Cultural Center:
Learn about the history of the Jewish community in the Tidewater region at this important museum: Housed in the Chevra Thelim Synagogue, this is a place where visitors from home and around the world can celebrate and learn about the Jewish history, faith and culture. The center houses artifacts and exhibits that reflect the history of the Jewish communities in the region as well as an eighteenth century Torah Scroll rescued from a synagogue in Trebic, Czechoslovakia that was a victim of the Holocaust. Plan your visit here
Lightship Portsmouth:
Dive into Portsmouth seafaring past with a visit to this museum boat, The Lightship Portsmouth. Built in 1915, the Lightship PORTSMOUTH served for 48 years off the coasts of Virginia, Delaware, and Massachusetts remaining at strategic locations for months at a time. Now a museum, the ship’s quarters are fitted out realistically and filled with fascinating artifacts, uniforms, photographs, models, and other curious items. In 1989, the Lightship PORTSMOUTH was designated a National Historic Landmark. Plan your visit here
Portsmouth Arts and Cultural Center:
Engage with thought provoking and fun visual art and cultural and educational experiences in this amazing museum in the heart of Olde Towne. The cultural center has rotating special exhibits and tons of programming from art to history and beyond. The center is located in an historic 1846 Courthouse bridging the past and present. Plan your visit here
Portsmouth Naval Shipyard Museum:
Chart a course for The Portsmouth Naval Shipyard Museum, where you can learn about Portsmouth’s over 250-year history of shipbuilding. The museum has engaging exhibits that bring the history of the shipyard to life from colonial times to the mid-twentieth century. Plan your trip here
Portsmouth Colored Community Library:
A nationally registered historic site, the Portsmouth Colored Community Library Museum is located inside a small, one-story brick building that served as the only library for Portsmouth’s African American community from 1945 until 1963, when the city’s main library was desegregated. Originally located on South Street near Effingham Street, the library was a treasure trove for the city’s African American residents, with over 10,000 books ranging from James Weldon Johnson’s Along This Way and Henrietta Buckmaster’s Let My People Go to Langston Hughes’ The Big Sea and Carter G. Woodson’s Mis-Education of the Negro. Plan your tour of this important part of Portsmouth African American History here
Emanuel African Methodist Episcopal Church: A Pillar of History
Founded in 1772, just three years before the American Revolution, Emanuel African Methodist Episcopal Church stands as the oldest African-American church in the area. Its original location on Glasgow Street met a tragic end in 1856 when it was “burned by wicked hands.” Undeterred, enslaved and free Black individuals came together, building the current structure entirely by hand in just one year, and dedicating it in 1857.
Emanuel also holds a proud place in history as a station on the Underground Railroad. Inside, you can still see the hiding places used by those seeking freedom, as well as the location of the water duct that allowed them to crawl to the Elizabeth River, where they could stow away on merchant ships. Remarkably, no enslaved person was ever caught within the church’s walls. The church still features its original stained glass windows and hand-carved benches and pews, preserving its historic charm.
Beyond its role in the fight for freedom, the church also served as a vital community hub. During a time when mail wasn’t delivered to African Americans, two dedicated gentlemen maintained post office boxes downtown specifically to receive mail for the congregation’s members. This meant Emanuel also functioned as a substitute post office for the people living in Lincolnville.
If you’d like to experience this incredible history firsthand, please call the church secretary at 757-393-2259 between 9 AM and 3 PM, Monday through Friday, to schedule an appointment for a tour.
Hill House Museum:
The Hill House (circa 1825) is a four-story antebellum English basement home, originally constructed in the Federal Style. As the home’s architecture and furnishings have evolved through many generations of the Hill family, the internal integrity of Hill House still remains. Few changes have been made to the house over the years with the exception of several additions connecting the original house with the once separate kitchen. Also, additional changes are apparent throughout the house as each generation placed their mark on the architecture from Federal to its current Victorian influence – Plan your visit here
Trinity Episcopal Church
This parish has been a beacon of light in Portsmouth for over 250 years. The original church was founded in 1762. The original parish church played witness to The Revolutionary War, when Benedict Arnold took control of Portsmouth in 1781. When the Patriot victory was secured at nearby Yorktown in October 1781, the church bell was rung so loudly it cracked. The original bell is still on display in the church. The current church was rebuilt in the 1830s and served as a hospital during the Civil War. Their historic churchyard is the final resting place for many patriots and the Naval commander James Barron, who is best known for his role as commander of The Chesapeake in the Chesapeake-Leopard Affair. This was a naval clash that happened off the coast of Norfolk, Virginia, on June 22, 1807. It involved the British ship HMS Leopard and the American frigate USS Chesapeake. The Leopard‘s crew pursued, attacked, and boarded the American ship, searching for deserters from the Royal Navy. The Chesapeake was unprepared for the assault and, after a brief exchange of fire where it only managed to fire one shot, its commander, James Barron, surrendered the vessel to the British. Read more about this often forgotten part of American history here. Interested in touring the historic churchyard and/or attending services. Click here to learn more about Trinity Church
Catch a show at The Commodore, This is historic 1945 Art Deco Theatre shows first-run movies, and serves delicious food. If you are a historic theatre buff The Commodore is your ticket to fun.
Choo-Choo across the rails of history at The Railroad Museum of Virginia: Located at Court Street and Wythe Street, next to Olde Towne Portsmouth and the Path of History Walking Tour area, this awesome museum, tells the story of the history of Virginia’s and America’s railroads and the people who build them through engaging exhibits with artifacts detailing the history of the railroads. This is great museum for kids and adults. Learn more here.
Explore Portsmouth Natural Beauty:
Hoffler Creek Wildlife Preserve:
This relaxing haven preserves 142 acres of the Hoffler Creek watershed. Hike over 3 miles of trails through four unique habitats: a riparian forest filled with pines and hardwoods, to a meadow of native wildflowers and grasses, a non-tidal fresh water lake and a tidal creek with its expansive salt marsh. This is a place where you can truly immerse yourself in the peace of nature, from kayaking to hiking and wildlife watching. More than 200 species of birds have been identified here, making it a haven for local birders. Plan your visit here.
Paradise Creek Nature Park:
This 40 acre waterfront park is an immersive conservation project to help restore the Paradise Creek habitat. Walk two miles of trails where you can traverse an old growth coastal oak woodland (a rarity along the Elizabeth River) and a restored saltwater marsh with a view of Paradise Creek. Birders will enjoy the diversity of birds that these various habitats attract. An impressive 160 species of birds have been documented at this successful restoration site. Plan your visit here
Fun for Kids in Portsmouth:
Fun for Kids: Portsmouth is a great city for families. From parks to museums there is always fun for kids of all ages in Portsmouth
Children’s Museum of Portsmouth: The Children’s Museum of Virginia is a place where families and caregivers with children ages 1-11 are encouraged to imagine, explore, and discover together through play. Children step inside a world where bubbles grow bigger than they are, where the forces of energy electrify and spark their imagination, where they can be a farmer, a banker, a scientist, a stargazer and more. Plan your visit here
Catch a Toad Trail: On the Middle Street Mall near the entrance to the Children’s Museum, you’ll see a large toad sculpture called “I’ve been Kissed.” A local writer developed a children’s book about a toad named Bufo and his search for his special friend. Cross the street from the Children’s Museum and pick up a Toads on High brochure from the Welcome Center. There are clues to follow to find all the toads on High Street. While the kids look for toads you can browse the shops. The toads are in the windows along the way. If you’d prefer to look at public art that will take you all over Olde Towne, you can pick up the Walk Your Art Out clue sheet at the Welcome Center and discover murals, sculptures, and more along the way. Trail Info
Portsmouth Splash Park: Beat the heat at this cool city park. The Splash Park offers twelve varieties of ground nozzles that spray water upwards out of the splash pad’s rain deck. This amazing attraction offers family fun for everyone. Website
Where to Stay:
There are many wonderful places to stay in Portsmouth depending on your budget and vibe. If you are looking to stay in Olde Towne I recommend the Quality Inn or Renaissance Hotel because you can walk everywhere.
Where to Eat:
Portsmouth is a foodie town with a variety of restaurants, especially in the Old Towne district.
On the Waterfront, enjoy scenic waterfront dining at restaurants like Thyme on the River, Fish and Slips and Foggy Point Bar and Grill
Other fan favorites include High Street Pizza and Pour House, Olde Towne Public House, Lobcouser…click here for more delicious restaurants
Destination Coffee: Somethings always brewing in Portsmouth’s local coffee shops. Get your java fix at popular coffee hotspots like The Coffee Shoppe in Portsmouth’s Olde Towne. Whatever ails you – coffee is ‘The Cure’ at this delicious coffee joint. Gather is another popular place to get a cup of Joe to power you through a busy day of Portsmouth exploration.
Plan YOUR Portsmouth Vacation
Ready to book your Portsmouth getaway Resources:
In our upcoming blogs, we’ll be exploring Newport News and then onto Hampton and Gloucester for more history and must-see sites.
Don’t forget to subscribe to the blog for the latest adventures.
You can also follow us on facebook for the latest blog posts, cool reels, daily history and travel tips
We also have a podcast and vlog – American Nomad Traveler is available on all streaming platforms through Buzzsprout and on YouTube
We are now on Substack for additional content from Travel to History to Art and beyond…
Hi, I’m Adele Lassiter, the travel enthusiast behind American Nomad Traveler. This blog where I share my love for history, cool museums, art, and travel tips. When I’m not writing, I’m a singer-songwriter with a passion for Americana music. Her new album is available here: adelelassiter.bandcamp.com
Interested in partnering with American Nomad or have an idea for a travel post? Contact us at americannomadtraveler@gmail.com or by using the Contact Form below:
One thought on “Must-See Portsmouth VA: Anchored in History, Alive with Adventure”