Explore Ontario’s Southwest:
10 Can’t-Miss Getaways
Just Across the Border!
Ready for your next road trip? Ontario’s Southwest is bursting with charming towns, scenic trails, local eats, and unique stays. We’ve rounded up 10 unforgettable itineraries across 10 amazing DMOs, perfect for adventure, flavour, and a little well-deserved R&R, all just a short drive from the US border.
Explore Our 10 Southwest Ontario Destinations
Can’t-Miss Events Across Ontario’s Southwest
Calling all US travellers! From vibrant festivals to one-of-a-kind celebrations, Ontario’s Southwest is packed with events that celebrate local flavours, history, and culture. Make your next weekend getaway unforgettable with experiences you can’t find anywhere else, just a short drive across the border.
Mark Your Calendar...
Sugar Bush Season
- Recurring daily, and ends on Apr 12, 2026
Eat and Drink Norfolk
- Recurring daily, and ends on Apr 11, 2026
Come From Away
- Recurring daily, and ends on May 24, 2026
Big Cheese Days
- Recurring weekly on Saturday, and ends on May 30, 2026
Caledonia May Long Weekend Celebration
- Recurring daily, and ends on May 18, 2026
RetroFest
- Recurring daily, and ends on May 23, 2026
Carrousel of the Nations
- Recurring weekly on Friday, Saturday, Sunday, and ends on Jun 21, 2026
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