"We wanted to find a way to create a destination place as Green Cove at 8 [p.m.] is pretty quiet." That's how Brian Knight explained it to Clay Today in July, when he and his wife Jennifer described Springside, the Walnut Street retail village they plan to open in 2027.

He's partly right. On an ordinary Tuesday, only a few downtown places stay open late. Downtown's busiest nights come from a city-run calendar of markets, parades and food truck nights, and from now through New Year's that calendar is about as full as it gets. Springside is a bet that a few dated nights a month can become every night. Before that happens, here's what's already open and on the schedule.

The Addresses That Stay Lit Past Eight

Within a few blocks of Spring Park, three places stand out for evening food and drink, based on their published hours and recent records:

1. Red's Wine Bar, 414 Walnut Street. Wine, beer and tapas, with live music, trivia and bingo nights. It's open until 10 p.m. Tuesday through Thursday and 11 p.m. on Friday and Saturday. Explore Clay updated its profile of Red's in September 2026.
2. Roger That Wings & Things, 232 Walnut Street. A wings spot that promotes itself for food, drinks and get-togethers. State inspection records show a completed inspection callback there on September 25, 2026.
3. La Casita Mexican Restaurant, 20 North Orange Avenue. Sit-down or takeout, with beer, wine and margaritas. It's open daily until 9 p.m. and until 9:30 p.m. on Friday and Saturday.

Red's goes three hours past Knight's 8 p.m. mark on a Friday. Walk from Red's to Roger That and you've covered the core of downtown's late-night food and drink, all on Walnut Street. If you know other spots that still keep evening hours, check them directly. We couldn't confirm current 2026 hours for some long-listed downtown names, so they aren't on this list.

The Walnut Street you walk tonight is also newer than it might seem. The city reopened the street after its Phase I streetscape work in September 2024. That two-year-old streetscape is the stage Springside is building on.

Spring Park Closes at Sunset, Then Hosts the Biggest Nights of the Month

Officially, Spring Park at 200 Spring Street is open from sunrise to sunset. Yet the park hosts downtown's largest evening crowds, because the city schedules special events there after dark.

Food Truck Friday shows how that works. When it returned on July 3, News4JAX reported 17 food trucks, more than 40 local vendors and live music, with Firewater Tent Revival of Atlantic Beach headlining. Guests could bring lawn chairs, blankets and coolers, and beer and wine were allowed. Hard liquor was not. The event runs on the first Friday of each month through November.

The October edition fell on October 2, so one Food Truck Friday is left this season, on November 6 from 5 to 9 p.m. After that, the park's evening schedule moves on to the holidays.

Every Evening on the Downtown Calendar Through December

These are the dated events in or near downtown between now and New Year's, mixed with a few weekend daytime staples:

Tales from the Clink is the only October event on Walnut Street itself. Clay Today's calendar describes it as a recreated trial plus tours of historic sites. It ends at 8 p.m., which leaves time to walk a few blocks to Red's for a later glass.

If your October weekends extend past downtown, Amazing Grace Farms at 4251 State Road 21 runs its Pumpkin Festival on several dates from October 9 through October 31. Hours on opening night, October 9, are 4 to 9 p.m.

December 5 Is the Night Downtown Fills Up

Christmas on Walnut Street lasts all day, from 10 a.m. to 9 p.m., but most of the crowd comes for the evening part. According to Clay Today's calendar, the 6 p.m. parade starts at the courthouse, follows Orange Avenue to City Hall, and loops back to the courthouse. The Spring Park tree lighting comes right after.

The parade turns down Orange Avenue, where La Casita sits at No. 20, so dinner along the route is an option if you book or arrive early. The Parade of Trees stays up in Spring Park all of December, and Letters to Santa runs there through December 20, so the park keeps its holiday look between the dated events.

What Springside Is Trying to Make Permanent

Every event in that table is a single dated night. Springside is the Knights' plan to give downtown a reason to stay busy on undated nights too. The Knights are Green Cove Springs natives. Brian Knight founded Pragmatic Works. Clay Today reports they bought property along Walnut Street, modeled the plan on St. George Street in St. Augustine, and plan five restaurants around a pedestrian walkway, including Italian and Southern concepts, plus room for an ice cream parlor, a spa and a food hall. No tenants have been named publicly, and we found no local reporting on the project since that July story.

The first piece is a building many longtime residents already know. The Knights bought the historic Gustafson House, which sat vacant and in poor condition for 59 years. In the early 1900s, Frank and Agnus Gustafson, known locally as Ma and Pa Gus, bought their first cow, Buttercup. They started selling dairy products to neighbors and nearby hotels, and that home business grew into Gustafson Farms.

The renovation keeps the original brick, doors, windows and flooring, and adds an elevator, a wine room, a bar, an outdoor patio and a private dining room. The plan puts casual dining downstairs and a more upscale experience upstairs. The kitchen will be run by Chef Cody Herman, whom Clay Today describes as Michelin-rated and who is coming home to family in Green Cove Springs. R. Hartwig Construction is doing the work, and the Knights are targeting a spring 2027 opening. Bobby Hartwig told the paper that residents who remember Ma and Pa Gus and Buttercup keep stopping by the job site to share stories about the house.

The River Half of the Plan

Springside covers Walnut Street. The city's plans cover the water a block away. City Pier already has a pavilion, fishing and boat slips, though no food vendor. The city's FY2026/27 capital plan, revised in July, lists City Pier Extension Phase II at $690,000: $490,000 from legislative delegation funds and $200,000 from surtax. The city's state funding request describes a longer fixed pier, a wave attenuator and a floating dock. It estimated construction from September 2026 to February 2028. We haven't found a public update confirming that work has started.

Further out, a St. Johns River Trail Phase II request describes a 3.6-mile multi-use path from Spring Park to the Shands Bridge Trail, with about half a mile running over the river. The request asks for design, engineering and permitting money, and estimates construction for 2027 through 2029. If it's built, Spring Park becomes a trailhead as well as an event lawn. For now, this fall's plan is simpler: Red's on a Friday, Food Truck Friday on November 6, and a spot on Orange Avenue by 6 p.m. on December 5.

Watching Springside and the Gustafson House take shape, or wondering how a livelier Walnut Street could change daily life a few blocks from the river? The Dana Hancock team keeps up with Clay County's downtown changes and is glad to talk through what they mean for your street. Work With Us.