For taking advantage of that 'up to (several) people can meet outside' rule or just spending time in fresh air. I'll gradually gather a list of places to meet people for conversation. Criteria: on the subway, or not too far from it; not too crowded on weekdays; ideally some takeout or coffee nearby.
Central Area:
- Chorley Park. Long walk from Summerhill Station or short bus ride from Rosedale Station. Not crowded on weekdays. Directly above the well-known Don Valley Brick Works. Nearby coffee on a quiet shopping street.
- Ramsden Park. On the subway (Rosedale Station). Saw that meetups were hosted there.
- Christie Pits Park. On the subway (Christie Station), relatively more crowded. Went to a meetup there. Next to Koreatown (many sit-down restaurants, for when those are allowed to open).
- Not checked yet -- Bickford Park. Near Christie Pits and on the subway (Christie Station), could be an alternate location.
- Queen's Park. On the subway (Museum Station). Last year TJEX hosted some meetups there on weekends, but it didn't work too well because the Parliament building nearby attracts protesters. There are other green spaces on the University of Toronto campus nearby.
- Queen's Park. On the subway (Museum Station). Last year TJEX hosted some meetups there on weekends, but it didn't work too well because the Parliament building nearby attracts protesters. There are other green spaces on the University of Toronto campus nearby.
- Forest Hill Village. On the St. Clair streetcar (from St. Clair or St. Clair West Stations). More of a shopping street, but there is a quiet neighbourhood and some parks in the vicinity.
Waterfront:
- Ontario Place. Some distance from the Exhibition streetcar line (509,511). Open access park (lakefront, fresh air), not too many people on weekdays.
West End:
- High Park. Near the subway (High Park Station). Very large, quiet on weekdays. Grenadier Cafe is actually operating with a reduced menu (coffee, ice cream, hot dogs, chili) even though Google Maps says it's closed.
North York?
- Not checked yet -- Muir Gardens and Ravine. Near the subway (Lawrence Station).
My ambition is to make a list of tourist sites in Toronto that are outdoors and don't charge admission. But for now I'm just listing neighbourhoods I remember that have a historic flavour and are not too insanely far from the city centre.
For biking, Toronto has an extensive ravine trail system (pdf, pdf of east side) along the Humber and Don rivers.
Some out of the way 'village' neighbourhoods (and other interesting places) that come to mind:
- Unionville Village historic district, fairly far out. Video in 2020, self-guided tour.
- Older neighbourhoods up on Yonge: Thornhill Village (walking tour) and Richmond Hill Village.
- Rosedale and Moore Park.
- Kleinburg and the nearby park below McMaster Art Gallery.
- University of Toronto Campus if you haven't been there yet.
Online sites with self-guided walking tours of different places. These tended to be biased towards more crowded areas:
- City of Toronto Architecture Tours. The tour of the The Annex is located in a more quiet neighbourhood.
- Heritage Toronto (also here) lists some self-guided tours.