Labor Day weekend 2026 is looking like a good one for Chautauqua County families. Whether your crew wants fireworks, a parade, a boat parade, a free night at the races, animals, a Harry Potter club, a festival, or just an excuse to get out of the house before the school-year routine fully takes over, there is plenty happening Friday through Monday.
Don’t be the family that finds out about the fun after it happened.
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Yes, send me the fun! →Here are 12 family-friendly Labor Day weekend events in Chautauqua County to add to your plans!
Last updated: August 31, 2026. Event details, weather, and schedules can change, so please use the links below to confirm before you go.
Friday, Sept. 4
🎶 Cassadaga Labor Day Festival: Street Dance
American Legion Post 1280, Cassadaga | 5:30–8:30 p.m.
Kick off the Cassadaga Labor Day Festival with a Friday-night Street Dance featuring Mock Pepper and food trucks. It is an easy, festive way to start a long weekend with the family.
Get event details for the Cassadaga Labor Day Festival >>
🎶 First Friday Westfield
Downtown Westfield | 5–8 p.m.
Take a Friday-evening stroll through Westfield, where Main Street businesses stay open late and families can browse street vendors, enjoy live music, and soak up a little small-town charm.
Get event details for First Friday Westfield >>
🍂 Findley Lake Harvest Festival
Findley Lake | Friday–Sunday
Findley Lake’s annual Harvest Festival brings three days of live music, food vendors, local shopping, craft vendors, a Family Fun Zone, and early-fall festival fun. It is an easy pick for families ready to trade summer weekends for cozy festival season.
Get event details for the Findley Lake Harvest Festival >>
Saturday, Sept. 5
🎉 Cassadaga Labor Day Festival: Cassadaga Days and Fireworks
Various locations in Cassadaga | Beginning at 8 a.m.
Saturday is a full day of festival fun in Cassadaga. Start with the CassadagaMan race at 8 a.m., then head to Cassadaga Days beginning at noon for food, a bounce house, dunk tank, vendors, local businesses, and live music from 5–7 p.m. Cap off the night with fireworks at 9 p.m. at Johnny Fessenden Ball Fields.
Get event details for the Cassadaga Labor Day Festival >>
🏃 Daniel Feather Memorial 5K and Kids' 1K Fun Run
Bergman Park, Jamestown | Kids' 1K at 9 a.m.; 5K at 9:30 a.m.
Kids 12 and under can take part in the Ron Graham Memorial 1K Fun Run before the Daniel Feather Memorial 5K Run/Walk. Proceeds support youth programming and scholarships through Chautauqua Striders.
Get event details for the Daniel Feather Memorial 5K and Kids' 1K >>
🪴 HousePlantApalooza
Mike's Nursery, Lakewood | noon–5 p.m.
This second annual plant festival brings together local vendors and businesses, food, raffles, and more. It is a nice stop for families with plant-loving grown-ups or kids who enjoy browsing something a little different.
Get event details for HousePlantApalooza >>
🏎️ FREE Admission Night at Stateline Speedway
Stateline Speedway, Busti | Grandstands open at 4 p.m.; racing begins at 7 p.m.
Grandstand admission is free for everyone at Westfield Ag & Turf Free Admission Night. Come early for the pre-race autograph session, then stay for seven classes of racing. The first 500 kids in grades K–5 will receive a free backpack with school supplies while supplies last.
Get event details for Free Admission Night at Stateline Speedway >>
🎨 Chautauqua-Lake Erie Art Trail
Locations countywide | Saturday and Sunday, 10 a.m.–5 p.m.
Make your own art-filled road trip through Chautauqua County during this self-guided open-studio and gallery tour. Meet artists, explore studios and hubs, pick up an Art Trail Passport, and see corners of the county you might not otherwise visit.
Get event details for the Chautauqua-Lake Erie Art Trail >>
Sunday, Sept. 6
🚤 Cassadaga Labor Day Festival: Farmers Market, Boat Parade, and Concert
Various locations in Cassadaga | 12:30–7 p.m.
Sunday’s Cassadaga Labor Day Festival lineup starts with the Farmers Market from 12:30–3:30 p.m. at Ames Common, plus a takeout chicken BBQ beginning at noon at American Legion Post 1280. Don’t miss the patriotic Boat Parade at 4:30 p.m. (lineup at the DEC Launch at 4:15 p.m.), followed by a free Aces & Eights concert from 5–7 p.m. at the Floating Stage at Cassadaga Beach.
Get event details for the Cassadaga Labor Day Festival >>
🎆 Jamestown Labor Day Festival
Bergman Park, Jamestown | noon–dark
Jamestown’s 45th annual Labor Day Festival has plenty to make a day of it: food, arts and crafts, kids’ lawn games, magic, community bingo, professional wrestling, live music, and an 8:30 p.m. fireworks extravaganza. Admission is free; parking is $5.
Get event details for the Jamestown Labor Day Festival >>
Monday, Sept. 7
🦆 Cassadaga Labor Day Festival: Grand Parade and Ducky Derby
Maple Avenue and Cassadaga Beach, Cassadaga | Beginning at 11 a.m.
Wrap up the Cassadaga Labor Day Festival with the Grand Parade at 11 a.m. on Maple Avenue, followed by the Annual Ducky Derby at noon at the Maple Avenue bridge. Then, at 1:30 p.m., join the Lawn Mower/Golf Cart/Bike Dice Run, starting at the beach and winding around the lake with chances to win prizes. For Ducky Derby tickets, call or text 716-720-3935.
Get event details for the Cassadaga Labor Day Festival >>
💥 Fritz & Lynn Seamens Labor Day Demolition Derby
Stateline Speedway, Busti | Grandstands open at 12:30 p.m.; derby begins at 3 p.m.
Car-loving kids will not want to miss this full afternoon of demolition-derby action. Watch full-size, compact, youth, and Powerwheels divisions, with BBQ and concessions available before the heats begin.
Get event details for the Labor Day Demolition Derby >>
Looking for even more things to do? Browse our full Chautauqua County events calendar for family fun happening all week long.
Know of an event we should add? Email karam@macaronikid.com!
