Headwaters Fun & Festive Finds

A hand-picked sample of our many year-round festivals, fairs and events too unique to classify. To make the most of them, bookmark our events page, subscribe to our email blast, or move up here.


Grand Valley Duck Race | Photo by: Pete Paterson


1. Grand Valley Lions 20th Anniversary Duck Race

What: Feel true community spirit all day long May 23, with free breakfasts, garage sales, tractor races, town dinners, and of course the great race itself, with all proceeds going to community needs.

When: May 23

Where: Grand Valley




Canadian Open Old Time Fiddle Championship in Shelburne, Ontario | Photo by: Pete Paterson

Handmade fiddle by Shelburne’s Jim Cheyne in 2003. The front of the fiddle is made from spruce wood sourced via the local works department from a local tree. The maple for the back of the fiddle was from Robinson’s Saw Mill in Shelburne.
The original hand-drawn paintings were done by Shelburne artist Sandy Harron and depict:
The first female Fiddlefest winner – Eleanor Townsend
The first seven-time Fiddlefest winner – Ed Gyurki
Everyone’s Favourite — Johnny Mooring
The Invincible – Vince Mountford
Shelburne’s Fiddleville State Setting


2. Canadian Open Old Time Fiddle Championship

What: Tradition and community at their toe-tapping best, in the 65th edition of this leading North American fiddle competition. Homemade country dinners and lots of dancing to work them off.

When: Aug. 5-9

Where: Shelburne




Orangeville Blues and Jazz Festival | Photo by: Pete Paterson

An annual tradition, the Blues Cruise features 12 bands; 200 cars; 3,000 people on Orangeville’s main drag as part of the Orangeville Blues and Jazz Festival.


3. Orangeville Blues and Jazz Festival

What: Stroll, sit and sway at this shut-down-the-whole-downtown music festival founded by Orangeville’s Larry Kurtz, with 80-plus acts from jazz & blues to gospel & soul, local food and drink, and fun events like a vintage car and motorcycle exhibition.

When: June 4-7

Where: Orangeville




Headwaters – A Taste of Maple | photo by: Pete Paterson

Headwaters celebrates the season with all things maple.


4. A Taste of Maple

What: Our trees work all year for this. Come up in late March, when the entire region creates maple-mad menus, treats, activities, tours and more, right when this sweetest of syrups is at its best.

When: Mar. 11 – Apr. 10, 2016

Where: Throughout Headwaters




Erin Fall Fair Ribbon | Photo by: Pete Paterson

Erin’s Fall Fair is an annual tradition for many on Thanksgiving weekend.


5. Erin Fall Fair

What: It doesn’t get more country than the 165th year of this classic Thanksgiving weekend event. Livestock and produce competitions, rides, country entertainment, car shows, dog shows, and way too much food.

When: Oct. 9 – 12

Where: Erin Fairgrounds