Calgary? Hmm, real winter. For me, its 2-5 day trips. I roll down my driveway for the most part, ( Boston, MA area) and go. Even 1 overnight is good. I've pedaled much of New England. House, wife, adult kids, not quitting job and pedaling for a month. 4-7 days is a good stretch I think. Try riding from home? Got a route or destination? Gear and bike? Planning is the fun part for me. Try "map my rides" or " ride with gps" The alone time? I treasure. For me, I like to get out of my comfort zone, stretch it a bit. I love to camp and mt bike almost every weekend. Bike packing is the perfect mix of the two. Try this, just do one over night, you don't even have to camp( credit card touring it's called) Ride somewhere, stay over night. Go back home the next day. Maybe by a different route. Just start and enjoy. Pretty helpful group here. Also try Bikepacker.com and Adventure cyclist, both will get you out the door.