The WinterSong Music Festival is returning to Whitchurch‑Stouffville, Ontario, from January 22 to 24, 2026, featuring more than 100 musical acts across the community. The three‑day event aims to boost winter tourism and support local shops and restaurants.
Organizers — Epidemic Music Group and Discover Stouffville (the Town of Whitchurch‑Stouffville tourism office) — say concerts will take place at 18 venues. These include Latcham Hall, the Stouffville Library, the Stained Glass Centre for the Performing Arts, and various downtown cafes, bars and other local businesses.
Headlined by Canadian musician Jim Cuddy, the 2026 festival also features an artisan market and a youth stage for emerging performers. WinterSong began as an annual celebration of a Guinness World Record set in 2017 at The Earl of Whitchurch pub for the “Longest Concert by Multiple Artists” (more than 437 hours).
By drawing visitors from across the Greater Toronto Area, organizers say the festival increases weekend bookings at local accommodations and brings more foot traffic to downtown businesses. While headline shows require paid tickets, many smaller performances held inside local businesses are free to attend.
