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One of the most appealing aspects of Portsmouth is its pedestrian-friendly Olde Towne Historic District. Here visitors can stroll from nearby hotels, marinas, and bed-and-breakfast inns to chef-owned restaurants, trendy shops and exquisite art galleries. We invite you to experience the charm of Olde Towne Portsmouth, where a short stroll covers a lot of territory!

Stroll Historic High Street

As you walk the streets, you will notice names like London, Queen, King and High—these names can be traced to Portsmouthʼs British heritage. The streets bear names significant to Col. William Crawford, who founded Portsmouth in 1752 and named it after his hometown in England. These streets, in turn, form squares with names mostly of British origin, such as Bloomsbury, London, Edinburgh and Glasgow.
The wide road through the middle of the new town was called High Street and still today bears the historic designation that mimicked the name of main streets in England. The layout and the names give Portsmouth a connection to its past and to its official “Sister City” of Portsmouth, England.
If you head west on High Street, youʼll find shops, restaurants, and museums. The Childrenʼs Museum of Virginia and the Virginia Sports Hall of Fame face each other on opposite sides of High Street, offering fun exhibits and interactive activities for people of all ages.
At 421 High Street, youʼll come across the Commodore Theatre. Listed on the National Register of Historic Places and Virginia Landmarks Register, this old-fashioned theater was built in 1945 and was at the time considered the best-equipped theater in Hampton Roads. Today, the Commodore Theatre has been meticulously restored and continues to be a popular place to catch the latest films.
After checking out the theater, head back east on High Street to the corner of Court Street and High Street, where the cityʼs founder created a town square. In the original layout for Portsmouth, these four corners were designated for a church, a market, a courthouse and a jail. On the northwest corner, youʼll see an imposing Greek Revival building, surrounded by a wrought-iron fence and nearly hidden behind the massive oak trees that shade its courtyard. Built in 1846, it served as the Norfolk County Courthouse until 1960. Now it is home to the Courthouse Galleries, an art museum with two spacious galleries of ever-changing exhibits. From the original hand-colored lithographs of John James Audubon to the 17th-century engravings that depict some of the earliest images of Virginia Indians, the Courthouse Galleries museum continually strives to promote a greater appreciation and understanding of the arts.
The Courthouse Galleries is more than just an art museum. Itʼs a relaxing gathering place where you can learn the art of growing Bonsai trees one week and see a demonstration of glass blowing the next. Every First Friday, the Courthouse Galleries typically offers free musical entertainment. On the First Sunday of each month, educational programs – such as gallery talks and seminars that complement the exhibits – are open to the public, also free of charge. Art classes, lectures, poetry readings and book signings round out the vast array of offerings at the museum.

Stroll Through the Historic District

Whether youʼre a history buff or just a want to take in the scenery, meandering the tree-lined streets of Olde Towne Portsmouth on foot is one of the best ways to see this picturesque community.
In a single square mile, Portsmouthʼs Olde Towne has the largest collection of architecturally noteworthy houses between Alexandria, Virginia, and Charleston, South Carolina. The city has dedicated itself to preserving these important pieces of architecture so generations to come can enjoy our quaint historic seaport.
Head north on Court Street and youʼll enter the Historic District—hundreds of historic homes and buildings fill this small and scenic quadrant of Portsmouth. On your right youʼll pass the historic Court Street Baptist Church—a more than 200-year old church that was built and crafted by hand. Tradition states that the altar rail was carved from trees that grew along North Street.
At the corner of London and Court streets, youʼll be surrounded by a series of historic homes built in the 1800s. On the northeast corner is the Joseph Parker House—built in 1874, the house is an excellent example of Victorian architecture, complete with exquisite brick and ironwork. At 423 London is a house circa 1846 that was used as a hospital during the Civil War, and later, an apothecary shop. The architecture of this house served as a model for houses built about 40 years later at 421 and 419 London Street. At 430 Court Street is the former home of prominent businessman William G. W. Parker, brother to Joseph Parker who lived across the street. The house has also been used as a boarding house and the lodge of the local chapter of the International Association of Machinists.
Keep walking down Court Street until you get to North Street—take a left and walk one block. On your right, you will find the Watts House. Colonel Demsey Watts built this house in 1799 on a hill between Dinwiddie and Washington streets. The home was moved to its current location in 1808. Congressman Henry Clay, Chief Black Hawk and President Andrew Jackson have all been guests there.
Turn right on Dinwiddie Street and head north. Youʼll have to go right on Waverly Boulevard, walk a block and then go left to arrive on Crawford Parkway, right on the water. If you head east up Crawford, you can visit Fort Nelson Park, a 3-acre park at the entrance to the nationʼs first Navy hospital, the Naval Medical Center Portsmouth, which was built in 1830 and has served the military through every major conflict from that time to the present. Today, the park is home to many artifacts and historical signs.
Head back east on Crawford, passing the scenic sailboats and marinas resting on the shores of Crawford Bay, named after the cityʼs founder Col. William Crawford, who was, fittingly, a wealthy merchant and ship owner.
After youʼve had enough of the view—and maybe a moment to rest your feet—head back south on Court Street. Almost immediately on your left is Peterʼs House, at 315 Court Street—Pierre LʼEnfant, the man who designed the street plan of Washington D.C., also designed this house, but never had it built. William Peters obtained the design plan and built the house in 1859. Take a right at North Street, and youʼll find several architectural treasures—the Elkʼs Lodge, circa 1892; the Gaskinʼs House, circa 1808 and home to the cityʼs first silversmith; and the Macon Hotel. On the next block, check out the Washington Reed House for an example of late-Georgian architecture; the Grice-Neely House, circa 1820, at 202 North Street for its exquisite ironwork; the Hill House, which was occupied by the Hill family until 1961 and is now home to the Portsmouth Historical Association; and the Patriot Inn, which served as a boarding house for ferry workers. The oldest portion of the home was built in 1772 and it now serves as a bed-and-breakfast. Youʼll find yourself back at Crawford Parkway again, so take a right on Crawford and then your next right on Glasgow St. Circle around the block and youʼll see six beautifully preserved historic homes—the Irish Row House, settled by Irish immigrants in the 19th century; 215 Glasgow, which once housed the city market; the Ball Nivison House, circa 1780 and an fascinating example of a “tax-dodger” house, (the gambrel roof coming to the first floor allowed owners to avoid paying English taxes on two-story homes); the Red Lion Tavern, circa 1700s, a tavern for British soldiers and local soldiers during the American Revolution; the Pass House, circa 1841, used by Union forces during the Civil War as the Federal Adjutant Generalʼs Office; and the Benthall-Brooks Row Houses, circa 1840s, built by a sea captain and a fine example of English basement homes. Perhaps after all these historic homes, you need a breath of fresh air. So head east toward the Elizabeth River again and youʼll find several places to rest and enjoy the view. If youʼre ready for more fascinating history, take a tour of the Lightship PORTSMOUTH Museum, a ship built in 1915 that served for 48 years off the coasts of Virginia, Delaware and Massachusetts, helping mariners avoid dangerous shoals and enter safely into harbors at night.
Follow the river back to the High Street Shopping District and end the day enjoying a delicious meal at one of Portsmouthʼs fine independently owned restaurants.

Stroll the Path of History

As visitors explore Olde Towne, theyʼll come across informational signs noting the history and significance of various sites. These sites are part of Portsmouthʼs Path of History, a self-guided walking tour that links two of the nationʼs oldest Navy facilities—the Naval Medical Center and the Naval Shipyard.
Stops between the two parks include a string of historical sites in Olde Towne. This self-guided walking tour includes several dozen points of interest, such as homes and hotels, churches and taverns, along with monuments and parks. A few of the highlights include: At Middle and North is the sprawling Macon House, an 1855 resort hotel that soon became a Civil War hospital and barracks. Now it is divided into three adjoining apartment houses, but evidence of the past remains in regimental numbers that were chiseled into the woodwork in some of the rooms.
The Watts House at North and Dinwiddie streets, the residence where President Andrew Jackson, Chief Black Hawk and Henry Clay were once guests. Peterʼs House on Court Street, an 1859 classic revival home designed by Pierre LʼEnfant. The Red Lion Tavern on London Street, a place of refreshment for British and local sailors before the American Revolution. During its renovation, old menus and a pit for cockfighting were found in the cellar.
Public parks serve as bookends to the Path of History. A one-acre park at the south end of the Path of History, near the Naval Shipyard, is called Gosport Park. This space features artifacts that represent key milestones in the shipyardʼs 200+ years of history. Of particular interest are two 75,000-pound propellers from naval supply ships, along with other interesting memorabilia, such as a refurbished sail from a former submarine and Navy guns that were once used on vessels built at the shipyard.
At the north end of the Path of History is a 3-acre park at the entrance to the nationʼs first Naval Hospital. Located near the gate of the Naval Medical Center Portsmouth, it is called Fort Nelson Park and was recently named a “Best New Facility” by the Virginia Recreation and Park Society. It is filled with artifacts and historical markers that tell the story of the nationʼs oldest Naval Hospital. The park is home to handsome brick walkways, placards describing local history and a scattering of Navy and Coast Guard artifacts – including warship guns and huge colored buoys. This medical institution was built in the 1830s and has served the military through every major conflict from that time to the present.
Also take note of the genuine British telephone booth that stands at the North Ferry Landing as a reminder of our sister city relationship with Portsmouth, England. You will also find mounted plaques on imported English street lanterns that signify Olde Towneʼs many architecturally and historically significant houses. We invite you to visit the entire "Path of History" or stop at various sites to learn about Portsmouth's history in a leisurely fashion.

Stroll The Waterfront

A pleasant way to start your walk is on the Portsmouth Seawall, a scenic walkway on the banks of the Elizabeth River. If youʼre lucky, you might catch a glimpse of one of the massive ships going in for repair at the Naval Shipyard in Portsmouth.
Adjacent to the Seawall, close to High Street Landing, youʼll find the Fresnel Lens, a lighthouse lens dating back to 1896 when it was a part of the Hog Island Light off the Great Machipongo Inlet on the Eastern Shore of Virginia. Standing 10 feet high, the lens is one of the largest and brightest of its kind, with more than 250 prisms of optical glass.
Walk north along the Elizabeth River, and the Seawall will lead you to High Street Landing, the first of two ferry landings. Connecting downtown Norfolk and Portsmouth, the ferry service is touted as the first of its kind in America, starting service as early as 1636. Of course, the boats are newer and faster these days, allowing passengers a quick trip across the river any time of day.
Overlooking the ferry stop at High Street Landing is the Seaboard Railroad Building, a historic building constructed in 1894 and used as Portsmouth City Hall until 1980. The circular, 5-story building was given to the city by the Seaboard Coast Line in 1958. It now houses a restaurant and art gallery and offers sweeping views of the river.


There are over 20 Historic Markers found in the Olde Towne area and along the Elizabeth River. Please click on the link below for a map with locations of all of Portsmouth's Historic Markers including history for each designation.

Biking in and around the historic district of Olde Towne Portsmouth can be done at a very leisurely and comfortable pace. Because Olde Towne is home to two marinas, many boaters docked at Tidewater Yacht and Ocean Marine keep folding travel bicycles on their vessels to ride to nearby restaurants, convenience stores, museums, art galleries and to venues like the Commodore Theatre or the NTELOS Wireless Pavilion. Other cyclists enjoy the views provided by Olde Towneʼs residential district, with its period homes dating back to the 18th and 19th centuries and its grand churches with their magnificent stained glass windows. While cycling in Olde Towne Portsmouth, please remember to share the road with vehicular traffic. Other important reminders include:

 Downtown Loop/Shuttle Bus:

"The Downtown Loop" Shuttle - Portsmouth, Virginia

Visitors to High Street Landing can now ride “The Downtown Loop” through Olde Towne. This new shuttle service is a convenient way for visitors to travel from the waterfront farther up High Street, into new eateries and stores downtown, while easing parking problems and reducing congestion. Two shuttle buses run by Hampton Roads Transit will circle downtown Portsmouth, traveling from hotels to marinas to a commuter parking lot and the Naval Medical Center. Service is timed to the arrival of the Elizabeth River Ferry at High Street Landing.

“The Downtown Loop” is a downtown shuttle serving local businesses, schools and residences operated by HRT. The Loop operates six days a week, Monday to Saturday.

From 10 a.m. to 8 p.m., the buses will operate every 15 minutes. From 7:00 a.m. to 10:00 a.m. and from 8 p.m. to 12 midnight each day, service will run in 30-minute intervals, timed to the arrival of the downtown ferry at High Street Landing.

Fares will be 50 cents per ride or $1.50 for an all-day pass. HRT also will make weekly and monthly commuter cards available.

Ferry Service:

HRT's Paddlewheel Ferry is a system of three 150-passenger paddle-wheel ferry boats, one of which is the world's first natural gas-powered pedestrian ferry. The Ferry travels bet ween North Landing-Portsmouth, High Street Landing-Portsmouth and Downtown Norfolk at The Waterside. It's fast, economical and offers a panoramic harbor view. The Ferry operates every 30 minutes with 15-minute service during the summer at peak times on weekends. Schedules are subject to change based on operating situations (weather, mechanical problems, etc.). The Ferry is wheelchair accessible and allows boarding passengers to walk on with their bicycles. High Street Landing Portsmouth- Located on the river end of High Street and is the most accessible to our five museums, restaurants and shopping district. High Street Landing is the first stop on the Portsmouth side and then continues to North Landing-Portsmouth. North Landing Portsmouth- Located next to the Portsmouth Visitors Center, the Renaissance Hotel and the Holiday Inn and an easy walking distance into the Olde Towne Historic District. North Landing Portsmouth leaves Portsmouth and crosses the Elizabeth River to Downtown Norfolk at the Waterside.

Take the Ferry for Fun
Day or night, riding the Ferry is a great way to get around. Restaurants, museums, shopping and more are all within walking distance of the docks.

Take the Ferry to Work
One of the best ways to avoid rush hour traffic, particularly in the Downtown Tunnel, is to commute to work on the Paddlewheel Ferry. Commuters can buy monthly discount passes aboard the Ferry on the first and last business day of each month.

Park & Sail Program
Use the Park & Sail program and you can park for FREE in Portsmouth and then take the Portsmouth Loop to the ferry landings. Call 1-800-700-RIDE for more information or log on to
Cash Fare: $1.00
Seniors and persons with disabilities: 50¢

Paddlewheel Ferry Schedule
Memorial Day to Labor Day 30 Minute Schedule
Weekdays High Street - 7:00am to 11:30pm
North Landing - 7:05am to 11:35pm
Waterside - 7:15am to 11:45pm
Weekends High Street - 10:00am to 11:30pm
North Landing - 10:05am to 11:35pm
Waterside - 10:15am to 11:45pm

Labor Day to Memorial Day 30 Minute Schedule
Monday-Thursday High Street- 7am - 9:30pm
North Landing - 7:05am - 9:35pm
Waterside - 7:15am - 9:45pm
Friday High Street- 7am - 11:30pm
North Landing - 7:05am - 11:35pm
Waterside - 7:15am - 11:45pm

Saturday High Street- 10am - 11:30pm
North Landing - 10:05am - 11:35pm
Waterside - 10:15am - 11:45pm
Sunday High Street- 10am - 11:30pm
North Landing - 10:05am - 11:35pm
Waterside - 10:15am - 11:45pm

*New Year's Eve service ends at 2am
No service on Thanksgiving and Christmas

Take the Ferry to Harbor Park!
The Harbor Park Ferry runs between North Landing in Portsmouth and Harbor Park in Norfolk. Service runs every 30 minutes beginning one hour before game time and continuing just after the game ends. Norfolk Tides Information:

30-Day Ferry Farecard: $30.00* | 5-Day Ferry Farecard: $8.00* | 3-Day FerryFarecard: $5.00*
Ways to Purchase Farecards
In person: Visit the HRT Offices at 1500 Monticello Avenue, Norfolk, VA 23510
By phone: Call HRT Customer Service at 757-222-6100

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