3 Must-Attend Community Events in Kingston This September |
From a rolling art tour to a classic car show and an 18th-century harvest celebration — here's what's happening in Kingston over the next two weeks |
Kingston's fall event season kicks into high gear over the next two weeks with three distinct celebrations that showcase the city's artistic spirit, automotive passion, and living history. Whether you're an art enthusiast, a car collector, or a history buff, there's something happening here for you.
11th Annual Art Walk Kingston
When: Saturday-Sunday, September 19-20, noon-5pm
The largest open studio tour in the Hudson Valley returns for its 11th year, transforming Kingston into a two-day art pilgrimage. More than 200 artists will showcase their work across 60 locations — from home studios to established galleries — spanning three distinct neighborhoods connected by bike lanes and rail trails.
This year's event features hand-embroidered textiles by Aurelie Hug, ceramics by Scott Zimmer, photography by Lynne Breitfeller, and portraiture paintings by Sharon Frey. Participating galleries include 68 Prince Street, Transart Gallery @107, Utopia, D.R.A.W., the Lace Mill, the International Museum of Dinnerware Design, Kingston Social Gallery, Station, and The Department of Things.
Saturday's special programming includes a steamroller print demonstration by the Neighborhood Print Studio and live music by M'Bollo accompanied by artist Nancy Ostrovsky. Printed maps will be available at Rough Draft, Village Coffee & Goods, Village Grocery, and Kingston Wine Company starting September 12. More info: artwalkkingston.com
6th Annual Uptown Car Show
When: Sunday, September 20, 11am-3pm
Classic cars, custom builds, and vintage favorites take over Kingston's historic Stockade District for the 6th annual Uptown Car Show. The event features 17 award categories with 28 total awards, including first-place trophies and second-place plaques chosen by professional judges.
Headlining the Pugsly's Barbershop Stage is rockabilly legend Reverend Horton Heat, with special performances by The Sci-Flies and Messer Chups. The show runs from 11am to 3pm, with judging cut-off at noon and awards announced at 3pm.
All show cars must register at Dietz Stadium parking lot, where pre-registered vehicles will obtain display cards before being directed to show parking. Day-of registration is available, but the first 50 pre-registrants receive a free 2026 Car Show dash plaque. Spectators can enjoy free parking at Dietz Stadium and Kingston Plaza. More info: mainetti.law/carshow
18th Century Autumn Fest
When: Saturday, October 3, 11am-4pm
Step back in time at Senate House State Historic Site's annual Autumn Fest, where visitors can experience key 18th-century activities that helped early Kingstonians prepare for winter. Demonstrations include blacksmithing, meat smoking, candle dipping, and apple pressing — all hands-on opportunities to try your hand at historical crafts.
The event features live performances of juggling, fire spitting, and unicycling alongside crafts for visitors of all ages. Guided tours of Senate House — New York's first capitol building, where the state's first government met in 1777 — are available, and the site's museum features two brand new exhibits.
All outdoor event activities are free and family-friendly, making this an accessible way to experience Kingston's revolutionary history while enjoying the crisp autumn air. More info: parks.ny.gov/historic-sites/18
Plan Your Weekend
With Art Walk Kingston spanning Saturday and Sunday, the Uptown Car Show on Sunday, and the Autumn Fest the following Saturday, Kingston offers a packed two weeks of community celebration. Each event is walkable or bikeable, with parking available at municipal lots and nearby facilities. Bring your appetite — food vendors will be on hand at all three events. |
Sep 26, 2026
3 Late October Live Music Events in Kingston NY You Can't Miss
From cult classic screenings to cello rock to Halloween cover band battles — Kingston's late October music scene has something for every taste
Sep 22, 2026
People's Place: 50 Years of Serving Kingston's Most Vulnerable Neighbors
Kingston's Community Hub for Food, Friendship, and Support Since 1970
Sep 22, 2026
Nekos-Dedrick's Pharmacy: A Kingston Institution for Generations
Kingston's oldest independent pharmacy continues to deliver personalized care with a smile
Sep 22, 2026
18th Century Autumnfest at Senate House Returns October 3-4, 2026
Step Back in Time at Kingston's Premier Revolutionary War Living History Event
3 Comments
Join the conversation
Reverend Horton Heat at a car show in Uptown Kingston is not something I expected to see on my Sunday plans but here we are. Feels like a weird combo but I kind of love it. Hope they get enough cars registered, last year the turnout felt a little thin on the Stockade blocks near Crown Street.
Greg MaloneHa, right? Reverend Horton Heat is such a random get for a Kingston street show but honestly rockabilly and old cars is a pretty natural pairing if you think about it. And yeah Crown Street did feel sparse last year. Hoping the pre-registration push helps fill things out a bit more this time.
Went to the Art Walk last year and honestly it was one of the best weekends I've had in a long time. The Lace Mill stop alone is worth the trip. Glad to see Lynne Breitfeller is participating this year, her photography is incredible. Already marking my calendar.