Share This Article
Summer in Caledon is filled with community festivals, fairs, food events, cultural celebrations, outdoor activities, farm experiences, markets, family-friendly events, and free things to do across the town.
From major events like Caledon Day and the Caledon Fair to Ribfest, Canada Day celebrations, arts festivals, and charming small-town experiences in Bolton and Caledon Village, this guide highlights the best Caledon summer events 2026 to help you plan your season.
June 10th to 14th – RBC Canadian Open
The RBC Canadian Open brings world-class golf to TPC Toronto at Osprey Valley, featuring professional players, tournament action, fan experiences, and a major sporting atmosphere in Caledon.
Where: TPC Toronto at Osprey Valley, Caledon
When: June 10th to 14th,
Admission: Ticketed
(Golf Tournament)
June 13th and 14th – Italian Heritage Day 2026
Italian Heritage Day celebrates Italian culture, food, music, vendors, community, and heritage in Downtown Bolton.
Where: Downtown Bolton, Caledon
When: June 13th and 14th, 8:00 am – 6:00 pm
Admission: Free
(Cultural Festival)
June 19th to 21st – Caledon Fair 2026
Caledon Fair returns with agricultural exhibits, live entertainment, midway attractions, food, competitions, vendors, and classic rural fair programming.
Where: Caledon Fairgrounds, Caledon Village
When: June 19th to 21st,
Admission: Ticketed
(Cultural Festival)
June 20th – Caledon Day
Caledon Day brings live music, food, local vendors, family activities, community programming, and a large outdoor celebration to Caledon East.
Where: Caledon East Community Complex
When: June 20th, 2:00 pm – 10:00 pm
Admission: Free
(Festival)
July 1st – Caledon Canada Day and Strawberry Festival
Caledon Canada Day and Strawberry Festival celebrates the holiday with food, community programming, vendors, entertainment, and family-friendly activities.
Where: 18297 Hurontario Street, Caledon Village
When: July 1st, 8:00 am – 4:00 pm
Admission: Free
(Festival)
July 3rd to 5th – Caledon Ribfest
Caledon Ribfest brings ribs, barbecue, food vendors, live music, family activities, and community festival energy to Bolton.
Where: 7 Timothy Street, Bolton
When:
July 3rd, 11:00 am – 11:00 pm
July 4th, 10:00 am – 11:00 pm
July 5th, 10:00 am – 7:00 pm
Admission: Free / Food available for purchase
(Food Festival)
August 14th – Midnight Madness
Midnight Madness transforms Downtown Bolton into a lively street festival with shopping, food, entertainment, vendors, and community programming.
Where: Downtown Bolton, Caledon
When: August 14th, 6:00 pm – 11:00 pm
Admission: Free
(Street Festival)
