Sleepy Hollow Music Festival 2026
Sat, Oct 03
|Kingsland Point Park
Everclear, The Smithereens and a full day of music in Sleepy Hollow, plus food trucks, beer gardens, a Kids Zone and the Headless Horseman himself. Gates 11am, music noon to 8pm.
Time & Location
Oct 03, 2026, 11:00 AM – 8:00 PM
Kingsland Point Park, 299 Palmer Ave, Richmond Hill, ON L4C 1P4, Canada
About the event
Sleepy Hollow in October is already a whole thing. Add two stages of live music and it turns into the best Halloween party you have been to.
The 2026 lineup: Everclear, The Smithereens featuring Marshall Crenshaw, Fastball, Sophie B. Hawkins, SoulShine: An Allman Brothers Experience, Anthony Giaccio & the Assortments, Rachel Ana Dobken, Imposters, The Altogether, and School of Rock Briarcliff Manor, plus a DJ set spinning 90s favorites. No overlapping sets, so you will not miss a minute of music.
There is a costume parade, Halloween crafts, a massive Kids Zone with inflatables and an instrument petting zoo, over a dozen food trucks, 30+ makers in the Makers Market, beer gardens, and a VIP lounge. Kids 12 and under are free with a ticketed adult, two kids per grownup.
Gates open at 11am. Music kicks off at noon. Everything wraps at 8pm. GA tickets are $62.50.
Kingsland Point Park,…