Where does downtown Portsmouth actually happen this fall? For years the answer pointed toward the water. This October it points up the hill. A crane is taking apart the old jail tower on the riverfront, and the roughly six-acre Crawford Bay site still has no developer. Meanwhile the busiest stretch of Olde Towne is the run of High Street between Water Street and Effingham Street. That stretch carries the month's biggest event, the newest storefronts, and the clearest signs of what comes next.
The waterfront will get its turn. The city has a timeline for it. That timeline runs past this year, though, and probably past the next two. Until then, High Street is doing the job that downtown Portsmouth has long expected the river to do.
The waterfront is a work zone, and will be for a while
The work most residents have seen is the demolition of the old Portsmouth City Jail and courthouse complex. Mayor Shannon Glover announced it at the State of the City address in May. He said the jail "has sat on some of the most valuable waterfront in the city" for decades. The city first planned to implode the building. Military officials judged that method unsafe because the jail sits so close to military facilities, so the tower is coming down piece by piece. 13NewsNow has described a crane chipping away at the structure.
The early completion dates have already slipped. The Virginian-Pilot reported that most of the active demolition began May 13. A city spokesperson expected it to wrap up by the end of that month. WHRO was still reporting demolition in progress on July 15. On Aug. 18, WAVY reported that Civic Center demolition had temporarily closed the exit from the City Hall Surface Parking Lot, Tuesday through Friday. The city has not published a firm finish date.
Glover has said what the cleared land is for. The city wants a pedestrian waterfront that runs from the Portsmouth Pavilion Stage all the way to Crawford Bay.
"So now we're tearing it down. We're creating space for something better." Mayor Shannon Glover, May 2026
Crawford Bay is a decision on a calendar
That pedestrian connection ends at Crawford Bay, and the site is still undecided. Three teams are competing for it: Cape Fear Development, Gold Key PHR and Hines. Economic Development Director Brian Donohue described what the city wants there as "new housing, ground floor commercial retail, so shopping, dining, entertainment uses, but also potential for a new hotel and of course public amenities." He pointed to Norfolk's Waterside, directly across the river, as an example of the energy the city has in mind.
Proposals were due Aug. 31. In August the Economic Development Authority approved up to $36,000 more for consultant AECOM to help evaluate the proposals and negotiate, with that support running through Dec. 31. Here is where the published schedule stood as of early October:
- September 2026: developer interviews
- November 2026: developer selection
- December 2026: presentation to City Council
That is a schedule, and no developer has been chosen. Donohue told WTKR in September that the process "will be somewhat time consuming." He estimated that once the city has a partner, construction could start "in the next 2 to 3 years." So even with a November pick, the riverfront between the Pavilion and Crawford Bay will mostly be cleared ground, construction fencing and plans for several more seasons.
So the season runs down High Street
That gap explains why October's calendar looks the way it does. The month's main event fills the street itself, not the water's edge.
High Street Fest returns on Saturday, Oct. 10, from 1 to 8 p.m. Admission is free. This is year two, and WAVY calls it the city's "second annual High Street Fest." The festival covers High Street from Water Street to Effingham Street, plus Court Street from Queen Street to King Street. Two stages run all day. The festival's official lineup:
- Main Stage: Bubba Ward, Better By Tuesday, Anthony Rosano & The Conqueroos, Rocky 7
- Second Stage: Fox and the Bear, The Band Monarch, PopTopic
WAVY lists the last act as "PopRock." The festival's own schedule says PopTopic. Vendor counts also differ by source. WAVY reports more than 50 food trucks. The city listing advertises more than 60 vendors, shops and restaurants, along with an all-day farmers market and to-go drinks. Main Street Director Liz Pasqualini called it "a celebration of everything that makes Portsmouth special – our people, our businesses, our creativity and our sense of community."
The rest of the month also stays close to the High Street corridor:
- Rock the Boat at HRT's Ferry, Thursday, Oct. 8, 4 to 6 p.m., at High Street Landing. The Tiki Bar Band plays, and the fare is $2 each way. This is the one October event on the water, and it starts at the foot of High Street.
- Portsmouth's Fall Wine Festival, Sunday, Oct. 18, noon to 6 p.m., at Festival Park, 16 Crawford Circle. As of this writing, the city's listing still shows the cost as TBD.
- Olde Towne Ghost Walk, Friday, Oct. 30, 5:30 to 9:30 p.m. Early-bird tickets cost $15 through Oct. 15. Regular admission is $20 starting Oct. 16.
The storefronts are filling in behind the festival
Once the festival tents come down, the street is still changing on its own.
At the corner of High and Washington, Half Full Bookstore opened in December 2025. Its owner is Tiana Skinner, a former public librarian. Next door, Samuel Lowry opened Track Team Headquarters, a music and clothing brand, in February 2026. WTKR reported that both businesses moved into units that had been empty. Skinner said opening in Olde Towne was a deliberate choice.
Farther down the street, there is a gap that should eventually fill. Roger Brown's Restaurant & Sports Bar at 316 High St. closed in February after more than 25 years. In late August, the Pilot reported that developer Lightwell plans a restaurant and roughly 30 apartments in the building. No restaurant tenant had been named at that point. Lightwell expected renovations to begin by fall and hoped to choose a restaurant within three months. The start date has already moved once. In February, WTKR reported the owner hoped work would begin in April.
The Economic Development Authority's June minutes track two more High Street buildings:
- 1220 High St. had an approved renovation permit, with work scheduled to start July 6 and finish Oct. 6, 2026. Tenant negotiations were still underway at the time.
- 1117–1121 High St. was still being renovated. Its schedule had been extended four weeks because of a plumbing-permit delay and unexpected conditions inside the building.
None of these updates is big on its own. Together, they show the street adding businesses one building at a time while the waterfront project is still being negotiated.
The street itself is next
High Street is getting its own makeover, and it runs on a multiyear timeline too. The city's High Street corridor project costs $24.5 million, and $19.3 million of that comes from a federal RAISE grant. The plans call for wider sidewalks, protected bike lanes, parking, streetscape work, and upgrades to utilities and fiber. The June minutes put completion around May 2030.
Compare that with the Crawford Bay estimate. If a developer is chosen in November and construction starts two to three years later, that start lands near the end of the High Street project. For the next few years, both ends of downtown could be under construction at once.
This month, that means a free festival on Oct. 10 and a $2 ferry party two days before it. A bookstore on the corner of High and Washington has been open since last December. A riverfront that will look very different by the time the next developer's plans become buildings. The developer selection is set for November, and the Council presentation is set for December.
If you own a home a few blocks from High Street and want to know how this fall's changes along the corridor affect its value, Conner and Company can walk you through it. Get Your Instant Home Valuation, then talk with our team about what downtown's next few years could mean for your street.
