a looooong time ago my buds and i had a Thursday nite ride at Calumet Co park. we'd bring dogs, friends, wives, kids (in order of importance) and some food. the kids and wives that did not ride would chill on the playground and lush grass by the lake while we did a few laps. we'd stop and take over kid watch while others rode and cooked/ate. it was very cool and a good way to get a ride in and have fam time simultaneously.
CCP is not the best trail in the area but they are dog and fam friendly and the loop is short enough that you can do a few before your peeps start wondering where you are.
i'm looking to resurrect this nite next season.
what nite we do it really does not matter but i'd like to make it a set thing. i know there are good road bike rides on Tues/Thurs and i'll be doing 1 of those (dont't hate. miles, miles, miles) so we can pick a nite that works for the masses.
if you are interested pm me your e-mail address and i'll add u to my cycling dist list. we'll kick it off as soon as the trails open in the spring.