Holiday Homes Tour

When: Saturday, December 14, 2024 from 1-5 PM
Starting point: Holiday Market
Red Lion Square Greenspace, Middle & Glasgow Streets
(closest address is 408 Middle Street, Portsmouth, VA 23704)
Rain or Shine
$20 Golden Ticket or $15 Standard Ticket

ONLINE TICKETING HAS CLOSED. Tickets will be sold in-person only on Saturday at the Holiday Market.

Experience the spirit of olde world charm of festively decorated homes in the heart of Portsmouth’s historic district during the Holiday Homes Tour from 1 to 6 PM on Saturday, December 14, 2024.

Neighbors open their decorated homes during this self-guided walking tour. Along the way, enjoy a holiday market, live music, carolers, seasonal greenery, and historical re-enactors.

Add to the magic and purchase a golden ticket which includes admission to the Hill House Museum. Step back in time and visit this historic home in Olde Towne furnished entirely with family belongings from the 19th and 20th centuries, collected through generations, and left in their original places. The Hill family lived in the home for over 150 years. In 1956, the three surviving Hill sisters—Elizabeth, then 79; Evelyn, then 85; and Frances, then age 83—made a gift of Hill House and its contents to the Portsmouth Historical Association. The additional cost will be given to the Hill House Museum to support conservation efforts.

The Olde Towne Portsmouth neighborhood dates back to 1740 and is the largest collection of historic homes between Alexandria, VA and Charleston, SC.

We look forward to sharing Olde Towne’s magic this season!


Where is Red Lion Square? Red Lion Square is the green space located on Middle Street at Glasgow Street. The closest address is 408 Middle St., Portsmouth, VA 23704.

Where should I park? Free parking is available in any city parking lot or garage. The nearest garage is located on the corner of Middle and London streets. There is also a residential lot on Court and Glasgow St. You may park in the residential lot for about 2 hours without a parking decal. For more information about parking in Downtown Portsmouth, click here.

How long is the tour? The self-guided tour is 7 homes in close proximity. You may choose how long you stay at each destination.

What does self-guided mean? Self-guided means that we will provide you a map to see the homes participating on the tour. Tour-goers will follow the map to each location and read descriptions and histories of the homes. There will not be a tour guide, so you may set your own pace or direction. Homeowners and  volunteers may be available to chat during the tour.

How do I get my tickets? Show your email confirmation on your phone or printed at check-in. We will also have a list of everyone who purchased tickets.

Where should I check-in for the event? Check-in at the Holiday Market at Red Lion Square at Middle & Glasgow St. Pick your wristband, map, and protective shoe booties.

Where do I pick up my map? At the Holiday Market at Red Lion Square at Middle & Glasgow St.

Where do I start the tour? The tour is self-guided. Visit homes in order of your choice. Start by picking up your wristband and map at the Holiday Market at Red Lion Square at Middle & Glasgow St.

What should I wear? Holiday Homes Tour is casual event. You’ll walk outside from home to home and the tours are inside. Layers and walking shoes are good choices. Some of our historic brick sidewalks can be uneven, so please walk with care. Homeowners may require protective shoe cover booties before entering their home.


Can I purchase a ticket on the day of the event? Yes, day of tickets will be available at the Holiday Market between 1 and 4 PM.

Do you take credit cards? Yes, we do!

Are children free? Yes, children 10 and younger are free.

May I bring my pet? Unfortunately, our furry friends will have to sit this one out. 

Is there a place to purchase food? There are many wonderful, local restaurants on High Street that we recommend if you’re planning to stop for a meal or drink! For a list, check out the Olde Towne Business Association’s website here. Our Holiday Market will feature holiday treats and a beverages to purchase.

Are there other events in the neighborhood? Yes, Downtown Portsmouth and Olde Towne will be filled with the magic of the season on December 10!

Portsmouth Olde Towne Farmers Market is open just about every Saturday at 10:00 AM at the corner of High and Court St. The market features local vendors with fresh veggies, meats, seafood, arts and crafts items, and more!

Olde Towne Holiday Music Festival from 11 AM – 5 PM along High Street. This festival will features a variety of Holiday music from school choirs, strolling carolers, and local musicians as well as children’s activities, roving historical re-enactors, and marshmallow roasting stations. For more information, click here

Is there a rain date? No, this tour is rain or shine. The tour features home decorated inside. If raining, please be mindful of tracking dirt and rain inside our homes. Protective shoe covering booties will be required.

Will a bathroom be available? Yes! There will Porta-Potties available at the Holiday Market. Tour homes will not have a bathroom available for guests.

This is non-smoking tour.

This event is sponsored by Olde Towne Portsmouth Civic League. 
Questions? Please check our FAQs.
Special THANK YOU to our Holiday Homes Tour Committee and Volunteers!

Online ticket sales close on Friday, December 13. Limited tickets will be sold in-person only on Saturday.

Tickets are non-refundable. Thank your for supporting the Olde Towne Portsmouth Civic League. 

Homes will close at 5:00 PM. 

Please arrive at least one hour prior to closing.

Olde Towne Portsmouth Civic League, the City of Portsmouth, and homeowners are not responsible for any injury, theft, or issue during this event. By purchasing a ticket, you assume responsibility of the aforementioned.