Let Our Lively Characters Guide You Through Historic Olde Towne Portsmouth, VA

9 Ratings
  • Live Guide
  • Instant Confirmation
  • E-Ticket

Our guides don't just dress the part. These expert interpreters, in the guise of real characters from Portsmouth's rich and colorful past, will entertain you with stories and songs, amuse you with word origins and colonial culture, and educate you on the history of the homes and their architectural features. Portsmouth boasts the largest collection of standing period architecture between Charleston and Alexandria, and has been an integral part of the history of our nation. Walk the streets where Benedict Arnold, Cornwallis, Lafayette, James Armistead, Billy Flora, Andrew Jackson, Chief Black Hawk, Mark Twain, and Martin Luther King Jr. walked. End at the Portsmouth Arts and Cultural Center where something new and interesting is always on display for your enjoyment. Then, find yourself in the heart of the restaurant district, with a plethora of eateries from which to choose.

Itinerary Details

This is a typical itinerary for this product

Stop At:

After gathering at the Welcome Center for introductions and some history related to the Coffee Shoppe, your guides will sing you a delightful little ditty about coming to America as you travel down Middle Street to your first stop.

Duration: 5 minutes

Stop At:

This quaint little eatery was once the site of Benedict Arnold's headquarters in Portsmouth. The most important spy of the American Revolution operated here, and you'll hear his story and many others once you meet your guide across the street. Early for the walk? Choose from a plethora of drink options and enjoy the hometown ambiance!

Duration: 2 minutes

Stop At:

Monument to Portsmouth's Revolutionary War Hero William "Billy" Flora. This free black livery owner closed up shop, grabbed his musket (Betsy) and joined an all white regiment. Listen to the account of his heroism at the Battle of Great Bridge.

Duration: 3 minutes

Stop At:

The Red Lion Tavern was established in 1752, the same year the town was founded. Learn the importance of an 18th century tavern and hear an amusing bawdy tune that might have been sung there!

Duration: 5 minutes

Stop At:

The Pass House is where folks came to get a pass to travel to Norfolk during the Union occupation of Portsmouth. Hear the unusual way one little old lady received her pass!

Duration: 3 minutes

Stop At:

See Portsmouth's own lightship museum and hear its history! There are only 17 lightships left in the U.S., and even fewer are maintained as museums. The interior of this museum is currently closed for renovations, but now that you know it's location, you can revisit it when it opens again. The Norfolk Naval Shipyard Museum is only one block away, and another point of interest you might consider after the walk (if open) or on your next visit.

Duration: 2 minutes

Stop At:

There is so much to see within just a few square blocks, that this portion of the tour is left to the discretion of our guides. Expect to see more beautiful historic homes and to hear more stories of days gone by as you stroll through the largest collection of standing period architecture between Charleston, South Carolina and Alexandria, Virginia

Duration: 30 minutes

Stop At:

Portsmouth Parish, known after the American Revolutionary War as Trinity Episcopal Church, dates back to 1762. Hear the stories of members of the congregation and its priests who played interesting roles in that war, as well as other wars that followed. It's bell was cracked ringing in the victory at Yorktown. The surrounding graveyard is the final resting place to two Revolutionary War veterans whose untimely deaths make for interesting ghost stories, indeed.

Duration: 10 minutes
This site uses cookies to improve your experience. By continuing to browse you agree to the use of cookies. Learn more in our Privacy Policy.