I live in Jackson's Point but buy my pass at Leatherdale Marine. A loop I enjoy often is taking B103 to Innisfil and run the lake to hop on the rail line near the 401 junction. Ride the rail line to 203 and then North on B across Couchiching. South to 207 ending up at Brechin and riding the lake back to Jackson's Point.
The longer loop is 421 to B, to B204 to Coldwater for lunch, and then run B104 back to B in Orillia. 207 to Brechin.