They weren't real pioneers, of course - they were employees and volunteers (often called interpreters) at multiple heritage sites that I visited while researching and writing my Master's thesis. But it didn't really matter - they dressed in traditional costumes and engaged in period-appropriate activities - so the sensation of stepping in the past was reinforced at every turn of the corner.
Now, I haven't been to every site in Ontario, but of the places I've been to, there is one I like the most - Westfield Heritage Village
There is definitely a benefit for being located far from the city - lots of room to play with. Because of its large territory, even 30+ buildings and a railroad with a locomotive still feel perfectly spread out. I may have been lucky, but every time I visit the village, it's quiet and almost deserted (school groups usually come during the week) - so it's just a pleasure to walk around, enter the buildings and talk to interpreters.
Meet my favourite interpreter at Westfield or should I say Captain Charles, the head of Queen's Rangers? He was the only one to stay in character and never to come out of it in the 20 minutes that I spent challenging him with naïve questions about different tools of "his" log cabin. Love the guy!
Any season is great for time travel, but my favourite is late fall. Every heritage site would have Christmas-inspired activities that you can participate in and, of course, the place will be nicely decorated for the holidays.
Doon Heritage Crossroads
Very similar to Westfield, but a slightly smaller village.
It has a great winter program:
leading up to Christmas, carol singers perform in an old Church every Sunday. And you can join them too! This is one of my great memories of Doon.
Black Creek Pioneer Village
Another village similar to Westfield and Doon. Because of proximity to Toronto, it's busier and the entrance is more expensive.
On the other hand, it's open every day and has more programs - like ghost tours, harvest festivals and Christmas dinners.
Before you tell me it's not a castle, consider that in Canada this is about as close as you can get to a castle. One of Canada's first premiers called this place home in the 19th century.
There are no costumed interpreters but some summer programs sound interesting - like gardening and cooking with period-appropriate ingredients and techniques.