I rode all over the neighborhood growing up, with my brother and friends and stuff. But I never rode to school. I remember the summer of 1995 when I took Driver's Ed, I rode my bike about 1.5 miles to the Community Center. But I never tried riding the ~1 mile farther to the high school. I did ride to the local Walmart a number of times in the 90's, before I started driving. That was about 2.5-3 miles each way and it always seemed like a hard ride to me. That was back when I used sidewalks along busy streets and such.
I took my son to the first day of Pre-K last year in the bike trailer, which because the road by our neighborhood isn't continuous, it's over 2.5 miles each way due to the roundabout way we have to go, and more like 3 miles for 3 months in winter when the park is closed for Christmas lights. If they would ever finish and connect the road by our neighborhood, my son's school would only be a quick 1.2 miles from the house.
I've been waiting for that road to get connected for over 10 years now.