Don't tell anyone where you are going. For a challenge hike at night. Bear cubs are cute and cuddly and should picked up and hugged. Don't worry, Mama bear won't mind 
Calgary and surrounding area are great for hiking. As someone who is starting out, go to some of the more popular hikes that have clearly out mapped out. Start with lower elevation ones to get use to hiking ~2-5km before doing the harder higher elevation and >5km routes. Especially in steeper hikes, get a good pair of shoes. Hiking can be tough on the ankles if walking on uneven or rocky paths. They don't have to be uber expensive, but be snug and breathable so you won't get sores (from the inside of your shoes rubbing against your foot). Lastly, I have much of a problem, but my friends of the fairer sex find it easier to use a walking stick, especially when going downhill. We were thinking it had something to do with men and women having a different centre of gravity.