Upcoming Winchester Events

Check out what's happening all around Winchester, ON

2026 South Mountain Fair

Thu, 13 Aug at 04:00 pm 2967 Lough Rd, K0E 1W0

The 14th Annual Art on the Waterfront

 Sat, 06 Jun at 10:00 am Main Street Free

Mother's Day Family Paint Day (6+ yrs)_LOVE BLOOMS

 Sat, 09 May at 10:00 am Sam Ault Arena CAD 40

14th Annual Art on the Waterfront

 Sat, 06 Jun at 10:00 am Main St., Chesterville, ON, Canada, Ontario K0C 1H0

Garden Party Mother’s Day Market

 Sat, 09 May at 10:00 am The Winchester Arena

Amanda and Kurtis’ Stag & Doe

Sat, 09 May at 08:00 pm The Winchester Arena

South Mountain Community Yard Sale 2026

 Sat, 09 May at 08:00 am South Mountain, Ontario

Russell Legion Annual Golf Tournament

 Sat, 12 Sep at 11:00 am Cloverdale Links Golf Course

SDG Geek-Con 2026

 Sat, 09 May at 10:00 am Chesterville and District Arena

South Mountain Pop-Up Market Taking Place During The South Mountain Community Yard Sale!

 Sat, 09 May at 08:00 am 10635 Maple st South Mountain

Winchester Multi-Sport Day Camp - For Kids Aged 6 - 12

 Mon, 29 Jun at 08:30 am The Winchester Arena

Chesterville Market 2026

 Sun, 21 Jun at 11:00 am Mike Dean Local Grocer : Chesterville / Bourget / Sharbot Lake (Chesterville, ON, Canada)

Brad and Robyn’s Stag and Doe

Sat, 27 Jun at 08:00 pm The Winchester Arena

2nd Annual Northern Thunder Vintage Motorcycle Show

 Sat, 01 Aug at 10:00 am Winchester Catering & Events

South Mountain Fair Demo Derby

 Thu, 13 Aug at 07:00 pm South Mountain Fair

AUDITION NOTICE : " LITTLE WOMEN" by Louisa May Alcot

 Wed, 20 May at 07:00 pm 478 Main Street, Winchester, ON, Canada, Ontario K0C2K0

Four Old Broads written by Leslie Kimbell

 Fri, 24 Apr at 07:30 pm Old Town Hall CAD 23

Joelle & Justin's Stag and Doe

Sat, 06 Jun at 08:00 pm 577 Main St, North Dundas, ON K0C, Canada

Keagan & Alexy’s Stag

 Sat, 30 May at 07:00 pm Vernon Recreation Hall

Farmer Johns Summer Party

 Sat, 25 Jul at 10:00 pm 13346 Forward Road Chesterville ont. k0c 1h0

Sandy Throw

 Sat, 09 May at 08:00 am 10668 Sandy Row, North Dundas, ON K0E 1W0, Canada

Sarah & Jacob's Stag & Doe Golf Tournament⛳

Sat, 18 Jul at 03:00 pm 10668 Sandy Row, North Dundas, ON K0E 1W0, Canada

MTAS Father Daughter Princess Gala

 Sat, 09 May at 06:00 pm 2967 Lough Rd

FIELD CROP RESEARCH DAY

 Tue, 30 Jun at 08:30 am 12088 Baker Rd CAD 90 to 113

Nation Valley ATV Club Annual General Meeting

 Tue, 12 May at 06:00 pm Country Kitchen Restaurant - Winchester

Farmer Johns Summer Party

 Sat, 25 Jul at 12:00 pm 13346 Forward Street, Chesterville, ON, Canada, Ontario K0C 1H0

Energy & Sound Healing

 Fri, 15 May at 06:30 pm Havre de Paix - 11464 County Road 3, Inkerman, ON

Alex & Cassie's Stag & Doe

Sat, 02 May at 07:00 pm Joel Steele Community Center - 577 Main Street West, Winchester, ON

The Outliers RC 3rd Annual Rodeo

 Sun, 07 Jun at 10:00 am 2260 County Road 7 Chesterville

Mindfulness Day Retreat

 Sat, 06 Jun at 09:00 am Briarcroft - 11397 County Road 3, Inkerman ON

Beginner mouse taxidermy class

 Sun, 31 May at 01:30 pm The Odd Stop CAD 161

Beltane Celebration 2026

 Sat, 02 May at 03:00 pm 11397 Stormont, Dundas and Glengarry County Road 3, Inkerman, ON K0E 1J0

Nation Valley Mud Run

 Sat, 20 Jun at 09:00 am PO Box 844, Winchester, ON, Canada, Ontario K0C 2K0

Maori Haka Workshop

 Sat, 16 May at 10:00 am Old Town Hall-Winchester, ON

Dairyfest 2026

 Sat, 08 Aug at 08:00 am 577 Main St W, Winchester, ON, Canada, Ontario K0C 2K0

Summer Nights Ride

 Sat, 22 Aug at 04:00 pm PO Box 844, Winchester, ON, Canada, Ontario K0C 2K0