Have you checked out the Weekender Ride in Ontario on May 2nd/3rd 2020? My long-time friend Mike Garrigan and Blacksmith Cycles are putting on this event for the second year. I will be riding Day-1 on one of the longer routes so it might be a good chance for us to connect on the road and/or after for dinner in Midland!
This event caught my eye because it is a low key weekend that could serve as a very good training block for a variety of abilities and goals while being a great social weekend as well. For many events, it is also timed well!
There is a range of routes (180km up to 350km split between the two days) and the price is quite good for a weekend that takes care of your accommodation, and route!