"I wanted to do something meaningful in my community, and this is what my idea blossomed into," Tiana Skinner told WTKR News 3 in March, describing Half Full Bookstore. She opened it in December 2025 at the corner of High and Washington streets in Olde Towne.
This is the shop's first full holiday season, and it starts at a useful time for Prentis Place. The neighborhood has to go elsewhere for its seasonal gatherings, and in 2026 the place it usually goes, High Street, has lost one of its longest-running rooms. Where the season lands this year depends on which doors on that street are open, and the newest ones have the busiest calendars.
The Neighborhood's Green Space Is Still a Budget Line
Prentis Place is a small neighborhood next to Prentis Park and Brighton. The Virginian-Pilot described the three as adjoining neighborhoods that share many of the same streets, with Interstate 264 and the Norfolk and Portsmouth Beltline tracks among their shared edges.
In May 2024, the Pilot reported that Prentis Place and Prentis Park both lacked city-owned parks and green space. Portsmouth's proposed capital plan that year included $350,000 to find a site for a park with a playground, a basketball court and other amenities. The project now has a name in the city's books. Portsmouth's financial report for the year ended June 30, 2025 lists a "Prentis Place Recreation Area" with $1,050,000 in total capital authorization, $83,500 spent that year and $966,500 unspent.
Until that money becomes a place, the holiday events closest to the neighborhood happen in nearby Olde Towne and at Portsmouth City Park. That makes the condition of High Street a neighborhood question, too.
High Street Lost Its Longest-Running Room in February
Roger Brown's Restaurant and Sports Bar at 316 High St. closed on February 8, 2026, after 25 years, WAVY reported. The Virginian-Pilot called it "a beloved landmark of Olde Towne," named for Virginia Sports Hall of Famer and six-time NFL Pro Bowl defensive tackle Roger Brown, who retired in Portsmouth and opened several restaurants.
The building has a plan for a second life. In that same August article, the Pilot reported that developer Tim Foley of Lightwell Development had bought the property and was working with the Norfolk design firm GARC on an estimated $8 million mixed-use project, using state and federal historic tax credits. The exterior would be preserved, the inside fully renovated, and a restaurant would stay on the ground floor below about 30 apartments called The Foundry. Foley told the paper he had "plenty of interest" from regional restaurants looking for an extra location. He expected work to begin within about a month and the apartments to take about nine months to build. "It's important for us to keep the identity of the neighborhood intact," he told the Pilot.
The city is also trying to bring more restaurants downtown. A City of Portsmouth community news release from October 13 announced a $15,000 state grant for a program to incubate and place restaurants. The program includes a proposed temporary food-truck test site at Zion Church.
Taken together, the long-running sit-down spot on High Street is between chapters this season, and the city is working on the restaurant gap. For now, small retail is doing most of the work of keeping the block busy.
A Bookstore Took Over the Calendar
Half Full Bookstore's events page has more on it for the rest of November than most of High Street. Skinner spent years in public libraries, according to WTKR, and the schedule looks like a library branch's, with storytimes, signings and a recurring game afternoon.
- Saturday, November 14: Illustrator Nicole Tadgell leads a meet and greet, storytime and signing of Dear Child of Mine, written by Sophia Robinson.
- Sunday, November 15: Meet & Mahjong with Hong Kong Mahjong Academy.
- Saturday, November 21: An event with Alise Pulliam.
- Sunday, November 22: An event with Kianna Rhodes, on the same day as the city's tree lighting a short walk away.
- Saturday, November 28: An event with Corina Deiters.
Check the bookstore's page for start times before you go. Next door is Track Team Headquarters, a music and clothing brand that Samuel Lowry opened in February 2026, according to WTKR. Both shops opened within a few months of each other and stand together at High and Washington, which makes that corner the newest active stretch of the street.
November 22 Brings the Season to High Street
The city's Tree Lighting Party runs Sunday, November 22, from 2 to 8 p.m. along High Street in Olde Towne, and it's free. Santa arrives by fire truck at the Portsmouth Art & Cultural Center, where kids' activities are set up. A School of Rock concert follows, and the Snow Queen and Sugar Plum Fairy light the tree at about 6 p.m. at the Children's Museum Mall.
The afternoon starts with activities at the art center courtyard and on Court Street and ends at the museum mall. If you're coming for the lighting, plan to be at the museum mall by 6 p.m.
November 28 Is When Everything Overlaps
The Saturday after Thanksgiving is the busiest day of the season, because five separate things start or fall on the same date. The Olde Towne Business Association has Small Business Saturday on its calendar for November 28. The city's other programs line up around it:
| Time | What | Where |
|---|---|---|
| 10 a.m. to 7 p.m. | Holiday Market, first of three Saturdays; local artists and makers, live demonstrations, music | High Street |
| 4 to 6 p.m., snow at 6 | Snow Wonders, first Saturday | Children's Museum of Virginia |
| 5 to 9 p.m. | Holiday Nights at the Park, opening night | Portsmouth City Park |
| All day | Small Business Saturday; Corina Deiters event at Half Full Bookstore | Olde Towne |
The city lists the Holiday Market as "subject to change," so check the event page that morning. The museum snowfall and the opening of Holiday Nights are an hour apart and in different parts of the city. Families who want both will need to choose an order. Holiday Nights is free, but the Pokey Smokey II train costs $2 for riders 3 and older, and the city asks visitors to book a train time in advance. The ride passes more than 150,000 lights, and the evening also includes live entertainment, free crafts, hot cocoa and a fully lit playground.
After the 28th, the Season Splits Between Two Addresses
From late November on, the calendar alternates between High Street during the day and City Park at night. December 12 is the one date when High Street fills the whole day.
- Fridays, Saturdays and select Sundays through December 20, 5 to 9 p.m.: Holiday Nights at Portsmouth City Park.
- Saturday, December 5, 10 a.m. to 7 p.m.: Second Holiday Market on High Street.
- Saturday, December 12: The third and final Holiday Market, 10 a.m. to 7 p.m., overlaps with the free Olde Towne Holiday Music Festival, 11 a.m. to 3 p.m., with music at the Middle Street Mall and Visitor Center and a showmobile stage at High and Court streets.
- Saturdays through December 26: Snow Wonders at the Children's Museum of Virginia, with extended hours from 4 to 6 p.m. and snow at 6.
The last Snow Wonders is on December 26, the Saturday after Christmas, a week after Holiday Nights closes on December 20. For anyone with family visiting over the holiday week, the museum is the city event still running.
If you'd like a neighbor's read on what's opening, closing or under construction between Prentis Place and High Street, and what it means for the blocks around you, the team at Debbie Childs is glad to talk it through. Let's Connect.
