Old Town Portsmouth & The Path Of History-Top 15 Highlights

One of my favorite aspects of the Hampton Roads area is the numerous historic areas. Not just the iconic Williamsburg and Jamestown reenactment areas, but the gorgeous historic streets sprinkled all over the modern city blocks where people still live in houses from the 1700s-1800s!

I love taking a turn and finding myself treading suddenly along the cobblestone and brick pathways instead of concrete, surrounded by ancient trees and gabled houses with gingerbread trim and sweeping front porches of an era gone by. Especially on a warm, east-coast day when a soft breeze is blowing in from the bay, and the sounds of modern life are distant, it’s so so easy to feel like I’ve stepped back in time. It’s incredibly relaxing and very much like a mini-vacation.

Houses in Olde Towne Portsmouth on the Path of History

One of these gorgeous historic neighborhoods that I can’t stop drooling over is Olde Towne Portsmouth. We’ve visited explicitly for the historical walking tour twice now. Honestly, I wouldn’t mind going back just to enjoy the peaceful atmosphere of those shady brick sidewalks several times again over the spring and summer.

The Path of History in Portsmouth

The Path of History self-guided walking tour takes you in a broad square that extends from the Elizabeth River to Effingham Street. It’ll take you at least 2-3 hours to see everything and more if you choose to tour the interiors of any buildings, such as the Courthouse, churches, or the Portsmouth Naval Shipyard Museum.

The Path of History tour includes 58 landmarks, including historical monuments and places of worship; however, several of these are somewhat disjointed from the main tour. I’d recommend following the map for the Olde Towne Sites, and you’ll see most of the monuments and churches along the way. You can always drive past the others on your way out.

Besides the opportunity to see some fantastic architecture, the historic walk also offers you the chance to learn about some fascinating history where it happened. You’ll pass houses where presidents and other heroic figures stayed and visit parks dedicated to the victims of tragedies. You’ll even get a magnificent view of the world’s largest and deepest natural harbor! I won’t spoil all the details for you, but I do want to share a few of my favorite highlights with you.

You can access a full walking tour map and guide for the Path of History from the Portsmouth Tourist website. It’s extremely helpful for completing the tour!

Highlights from the Path of History Historic Tour

1. Commodore Theater

The Commodore Theater is a gorgeous restored movie theatre built in 1945. While small, the theater features state-of-the-art video and sound systems, as well as the opportunity to enjoy fine dining during your visit! Besides the cool historical aspect, the building also has gorgeous Art Deco features that you’ll want to check out.

2. Court Street Baptist Church

If you enjoy Romanesque Revival architecture, you’ll immediately love the gorgeous details of Court Street Baptist Church. The original church building, founded in 1789, burned down and was rebuilt in 1901. The current building is made of pink granite, which gives it such a beautiful and unique appeal. It also has lovely stained glass windows throughout! You can visit the interior Monday-Friday from 8 am to 4 pm.

3. Joseph Parker House

Joseph Parker House Portsmouth, VA — *Joseph Parker House*

This lovely brick residence features delicate Victorian architecture along with ornate ironwork and a decorative roof. It was built in 1874 by Joseph Parker for his family of 12 children! The house has 14-foot ceilings and, at one point, a private chapel for the family. Directly across the street, you can also view the impressive home of his brother, William Parker, who had 16 kids!

4. Glasgow Street Park

Glasgow Street Park Cemetery and Memorial, Portsmouth, Va — *Glasgow Street Park*

If you enjoy facts and memorabilia about the War for Independence, Glasgow Street Park is a good stop for you. This tiny, peaceful area is dedicated to the Virginians who fought in the war. You can view a couple of monuments and several historic graves here, then sit in the shade to enjoy the park and birds.

5. Elk’s Lodge

The Elk’s Lodge is another lovely example of Romanesque Revival architecture. The house was built in 1894 by the Armistead family. It’s an imposing building with round towers capped with green peaks, high archways, and a solid brick exterior. It was converted into an Elk’s Lodge in the 20th century, but locals also know it as the imaginary castle of Dr. Madblood, an old Hampton Roads TV series from the ’80s.

6. Yellow Fever Park

Yellow Fever Park, Portsmouth, VA — *Yellow Fever Park*

The Yellow Fever Park is both pretty and sobering at the same time. This small park commemorates the Portsmouth residents who died in the Yellow Fever Epidemic of 1855. A plaque details the events of the epidemic and points out a nearby house that served as an orphanage for children whose parents died from yellow fever. The actual park is quite lovely, with multi-colored brick pathways lined with flowers, a few benches, and some shaded trees.

7. The Watts House

House of Colonel Demsey Watts, Portsmouth, VA — *Demsey Watts House*

Directly across from Yellow Fever Park sets the Watts House, famous for hosting Henry Clay, Chief Black Hawk, and President Andrew Jackson! Colonel Demsey Watts built this lovely home in 1799. It was actually originally built in a different location about 6 streets south, but he had it moved to this (apparently) more favorable spot 9 years later!

8. Fort Nelson Park

Right next to the Portsmouth Naval Hospital, you can visit Fort Nelson Park, named for the historic fort which used to reside here. The fort was built, destroyed, and rebuilt several times between 1776 and 1862 but was eventually decimated for good by Confederate soldiers. The current park area has many plaques around the area detailing facts about the fort and hospital. It also displays several impressive artillery and naval items, almost like modern art.

9. Macon Hotel

Macon House Hotel, Portsmouth, VA — *Macon House Hotel*

This lovely building opened as a resort hotel back in 1855. The attached house was built in 1830 and served as the owner’s residence. Visitors would come to enjoy the gardens and fresh water of the Elizabeth River nearby, as well as the ocean views from the hotel. At one point, the British Consulate even lived here because of its luxurious accommodations! For a short time during the Civil War, the hotel was converted into a Union hospital, and you can still see where wounded soldiers carved their names into the wooden floor. Currently, the building serves as three sections of apartment buildings.

10. The Washington-Reed House

The Washington-Reed House was built in the 1790s and exemplifies Georgian-style architecture. It’s absolutely lovely with its plethora of decorative windows and columned entrances. And a fun fact: the street signs are actually attached to the corner of the house! You can see them right behind the light pole in this picture.

11. Hill House

The Hill House is a tall, box-like home constructed from bright red brick and trimmed in crisp white accents. It dates back to 1825, when Colonel John Thompson built it. It remained in the Thompson family until 1961, when it was willed to the Portsmouth Historical Society, along with all the original furnishings! You can tour it for $5 on Saturday afternoons or call to make an appointment.

12. 215 Glasgow Street

Original city Market, Olde Towne Portsmouth, VA — *215 Glasgow Street*

This white brick house has a rather fascinating history and some cool features. The first floor was built in the early 1800s as a residence, but the second floor was added around 1870 and served as the city market! You can see that the windows on the second floor don’t quite line up with the first-floor ones, and, inside, you can still see the stall numbers on the roof beams of the second story. It also has a “busy body” system installed on the second floor where residents could spy out onto the streets unseen!

13. The Nivison-Ball House

This quaint two-story home saw a lot of history in its day. Recent research indicates that it was built in 1752 (not 1784 as previously thought) and originally had a false roof on a second floor to avoid taxation! The house was built over on Crawford Street and relocated to its current location due to a railroad track. It served as a barracks during the War of 1812 and hosted General Lafayette in 1824 and President Andrew Jackson in 1833!

*Side note: Colonial–Although it’s not included in the Path of History Tour, the beautiful white house across the street is very noteworthy. It’s a Greek Revival House built in 1835. You’ll notice the gorgeous columns, house-wide porches, and fancy triangle roof details. In 1901, a third floor was added by literally raising the roof and reattaching it to the new story!

14. Red Lion Tavern

The Red Lion dates back to the 1700s when it served as a local haunt for sailors and British soldiers. It was also a popular spot for cockfighting, indicated by the cockfighting pit discovered in the building’s basement during renovations.

15. Lightship Portsmouth

The Lightship Portsmouth Museum — *Lightship Portsmouth*

The Lightship Portsmouth is one of only a few surviving lightships from her era! She was built in 1915 and served in several locations during her 48 years. Now a national landmark, she’s been dry-docked here in Portsmouth since 1964 and is open for tours! You can learn about the lightships’ duties and view plenty of memorabilia in the ship’s quarters.

Closing Thoughts on Portsmouth and the Path of History

With the walking tour being so extensive and primarily on old brick walkways, you need to wear very comfortable shoes! Anything with a heel is bad news because there are cracks in places and sections of the path where tree roots have made the bricks pop up unevenly.

I also recommend parking in the Middle Street Garage. It’s located right near where the tour starts and ends, and parking is cheap during the week and free on weekends.

If you’re interested in touring any of the buildings, it would be wise to call ahead and plan your timeline accordingly so you don’t miss any reserved tour times.

Finally, do it on a beautiful day! You’ll enjoy the neighborhoods and the bay so much when the sun is shining and the ocean breeze isn’t bone-chilling!

I hope you enjoyed this week’s post and that you make plans to visit Olde Towne Portsmouth this spring or summer!

As always, thanks for stopping by and reading Carried Away Travels. Your support means the world to me!

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Happy travels!