5 Family-Friendly Events in Kingston This September 2026

September in Kingston is packed with events that bring families outdoors before the leaves turn. Here are five verified happenings worth putting on the calendar.

1. Hooley on the Hudson — Sunday, September 6

The 25th annual Hooley on the Hudson takes over T.R. Gallo Waterfront Park (1 Broadway) from 11:30 a.m. to 8 p.m. Three stages of live Irish music, step dancing, craft and food vendors, and a Parade of Dignitaries kick off the day. For families, the Lil' Hooligans Tent run by Play Haven offers free crafts, face painting, a shaded play area, and diaper-changing stations from noon to 5 p.m. Admission is free, with shuttle service from city parking lots.

Register for Lil' Hooligans on Eventbrite.

2. Tour de Kingston — Saturday, September 12

The 21st annual Tour de Kingston starts and finishes at Forsyth Park (125 Lucas Avenue). The 5-Mile Family Fun Ride leaves at 10 a.m. — flat, traffic-escorted, and completely free. Kids get a yellow Tour de Kingston T-shirt, and free helmets are available for those who need them. A bike safety booth runs all morning. The ride benefits YMCA youth bicycle safety programs. Registration opens at 7:30 a.m.; online deadline is September 10.

3. Kaatsbaan Annual Festival — September 5 & 12

Kaatsbaan Cultural Park (120 Broadway, Tivoli) hosts its annual festival across three Saturdays — the September dates feature storytelling, dance, and outdoor performances on the Mountain Stage with Catskill views. All shows run about an hour and are all-ages. September 5 centers on playwrights and a cabaret sing-along; September 12 closes with large-ensemble dance. Tickets start at $25, $15 for students. Combo discounts available.

4. Hudson River Hooray! Concert for Kids — Saturday, September 26

At 2 p.m., the Hudson River Maritime Museum (50 Rondout Landing) hosts an interactive concert with Emily Music for Kids. Families sing, dance, and learn songs about boats, sailing, fishing, and Pete Seeger's Hudson River legacy. Tickets are $9 for adults, $5 for children 12 and under. Details and tickets here

5. Play Haven at the Kingston Farmers Market — Saturdays, September 5–26

Every Saturday through the season, Play Haven Play Haven sets up a free kids' activity tent at the Kingston Farmers Market (285 Wall Street, Courthouse lot), 9 a.m. to 1 p.m. Expect crafts, open play, and seasonal themes — a low-key way to keep little ones entertained while you shop local produce and prepared foods.