September is the best month in the calendar to be from here. That is opinion and I will stand behind it. What is not opinion is the overlap: fair season and the first of the colour arrive in the same few weeks.
Eight worth the drive this month — and for once, all five of the regions we serve are on the list.
September 17–20 · Haliburton Highlands
Hike Haliburton
The twenty-third edition of what its organizers call Canada’s largest hiking festival: more than thirty-five guided hikes led by local volunteers, plus self-guided routes and ticketed excursions with local outfitters. The guided hikes are free, but they require registration — book before you drive up. ColourFest, a family festival at Head Lake Park in Haliburton, runs alongside it on the 19th. Details →
September 18–19 · Oro-Medonte Fairgrounds
The 172nd Oro World’s Fair
The 172nd edition, which puts it among the oldest fairs in Simcoe County. Livestock, the school fair, the exhibit halls and the midway, at the fairgrounds at Sideroad 15 & 16 East in Oro Station. If you have never been to a proper agricultural fair, this is the one to start with. Details →
September 18–20 · JD Lang Park, Bracebridge
Bracebridge Fall Fair & Horse Show
Midway rides, classic carnival games, the horse show, a petting zoo, interactive exhibits and a serious lineup of food vendors. Three days of it, on the fairgrounds at JD Lang Park. Details →
September 19–20 · Port of Orillia
Couchiching Fest
An artisan and vendor marketplace right on the water at the Port of Orillia, run through the Orillia District Chamber of Commerce. The waterfront is the best room in the city, and this is a good excuse to spend a day in it. Details →
September 23–27 · 50 Exhibition Way, Lindsay
The LEX — The Lindsay Exhibition
Home to one of the largest agricultural fairs in Ontario, by its organizers’ own description, and five full days of it. If you are anywhere in the Kawarthas at the end of the month, this is the event of the season. Details →
September 25–27 · 11 Michael Anne Drive, Coldwater
Coldwater Fall Fair
The village fair, three days, and about as close to the archetype as these things get. A short drive up Highway 12 from Orillia. Details →
September 26–27 · Gravenhurst
Gravenhurst Autumn Arts Tour
A self-guided weekend tour of local studios and makers, run by the Town of Gravenhurst and scheduled for the autumn season. A good excuse to drive some back roads with a map and no particular hurry. Details →
September 27 · Stockey Centre, Parry Sound
Dinner Theatre: Tom Thomson’s Wake
Presented by Shipyard Kitchen Party at the Charles W. Stockey Centre on Bay Street, from 4:30. Thomson painted Georgian Bay and Parry Sound sits on it, which makes this about the right room for the subject. The Stockey’s September season is worth a scan generally — there is something on most weeks. Details →
Two for the first weekend of October
Fair season does not quite end with the month. The Bobcaygeon Fall Fair runs October 1–3 at 47 Mansfield Street (details →), and the 176th Orillia Fall Fair runs October 2–4 at ODAS Park (details →). Worth knowing that the Orillia fair is not actually in Orillia — ODAS Park sits on forty-five acres in Severn Township, just outside the city limits.
Dates and details were confirmed with each organizer at the time of writing, but fair weekends do occasionally move — check the organizer’s page before you set out.
If any of this has you looking at the towns as well as the events, that is usually how it starts. I have known this area my whole life and have been serving these waters since 2005, and I am always happy to talk about what it is actually like to live in any corner of them — no agenda, just answers.
Lake Country Real Estate Team | eXp Realty | Serving Simcoe County, Muskoka, Parry Sound, Kawartha Lakes & Haliburton
