Sightseeing in Portsmouth

Portsmouth Sightseeing

A history lover’s dream come true

From its antique and specialty stores to its shade-drenched streets, Olde Towne Portsmouth is much more than one of the area’s most pleasant places to take a stroll. It’s a history lover’s dream come true. In a single square mile, the Olde Towne Historic District chronicles  300 years of history in one of the largest collections of antique homes south of Alexandria. Legend has it that Benedict Arnold was held captive in one of the homes. Another was used by Union Forces to issue passes during the Civil War, while yet another concealed medicine for Confederate soldiers. You can explore this national treasure through a self-guided walking tour (available at the Visitor Information Center) or  during seasonal lantern tours or candlelight home tours during special occasions. Here are just a few ways to see Olde Towne:


Path of History Walking Tour

Path of History brochure coverA self-guided walking tour of Olde Towne that takes you to 45 sites in the historic district, about one mile total.

A 1-acre park is at the south end of the "Path of History," near the Naval Shipyard. The park has brick walkways and two 75,000-pound propellers from naval supply ships. Signs featuring key milestones in the Naval Shipyard's 200+ year history are displayed, along with various artifacts, such as a refurbished sail from a former submarine and Navy guns that were once used on vessels built at the shipyard.

The north end of the "Path of History" is a 3-acre park at the entrance to the nation’s first Navy hospital. Located near the gate of the Naval Medical Center Portsmouth, the park is home to artifacts and historical signs. This medical institution was built in 1830 and has served the military through every major conflict from that time to the present.

Stops between the two parks include the Fresnel Lens, historic homes like the Pass House and the Hill House, and places of worship, such as Chevra T’helim Temple and Court Street Baptist Church. Visit the entire "Path of History" or stop at various sites to learn about Portsmouth's history in a leisurely fashion.

Download your brochure here or pick one up at the Portsmouth Visitor Information Center.
(757) 393-5111


Olde Towne Horse & Carriage Rides

Experience the streets of Olde Towne during a horse and carriage ride. By appointment only. For reservations, call (757) 635-9963 or e-mail


The Railroad Museum of Virginia

This new museum-on-the-tracks features a five-car train, with a 1910-era steam locomotive, two walk-through gallery mail cars, a dining car, antique Norfolk-Southern caboose, and a depot-style platform. Located near the nTELOS Pavilion in Olde Towne Portsmouth.

Hours: 10 a.m. - 4 p.m. Fridays and Saturdays.