Yes! There are some baby sitting options in town (https://www.cbbabysitters.com/) if you would like a parents-only night.
Quickest way: There are short shuttle flights from DIA to Gunnison if you want the quicker option without the drive. Gunnison is about 30 min from Crested Butte. Scenic Way: If you are up for a drive, flying into DIA is the cheapest option. It does entail a 4-4.5 hour drive. BUT, you will be driving through the beautiful Rocky Mountains!
All of the events of the weekend are happening in Crested Butte proper. Crested Butte South and Mount Crested Butte are nearby and great options to stay. The main difference is that Mount Crested Butte has more hotel and condo options since it is the site of the ski resort. There is also a free shuttle that takes you between town and Mount Crested Butte. Crested Butte South is only 15 minutes away and has many more single-family Airbnb options.
Crested Butte is VERY walkable. People mostly get around on bikes, but you can easily walk from one end of town to the other. There is also a free town shuttle that takes you from Mount Crested Butte to town. There is a free commuter bus that takes you from Crested Butte South as well. Many trails are accessible from town and all of our events are easily walkable. So you can ditch the car once you are here if you want!
Yes you can! Wheelies and Waves, Float Shack, Alpineer, Big Al's Bike Shop are all good options.
There are a couple grocery stores in town if you want to grab some essentials. Clark's Market (a little larger) and Mountain Earth (smaller organic grocer). Be aware that there is usually a mountain town premium. So if you are driving from Denver it might be worth grabbing some things down there first.
Up a new notches from casual but be comfortable!