Lots of possibilities that we've never been able to fully exploit. Part of the issue is that the three trails not only start in three different places but end in three different places. Another is that running it as an age group overnight makes a more strenuous hike a harder sell because the likelihood is that it will be a mix of stronger and weaker hikers. Here are the choices and some of the issues around them:
Drive Time: 1 hr 45 min
Hike Time: 2 hours each way
Swim: Tumbledown Pond
Age/Ability: Older (13-15)
Parker's Ridge Trail: This is the most gradual of the trails but also the longest. It also comes to an overlook above Tumbledown Pond and descends. Matt Strudwick led a trip day version on this trail and ran out of time. No one had the energy to descend to the pond knowing they would have to climb back up to make the return trip. I considered this route for an overnight once hoping to use an old shelter at the trailhead. And although the shelter is no longer available it's something we might still consider as a route after an overnight at Coos Canyon.
Loop & Brook Trails: To my knowledge, this is something we haven't tried because the trailheads are 1.4 miles apart and the Loop Trail in particular would be a difficult descent (iron rungs leading through an opening in the boulders) which is why we usually hike the Brook Trail both ways. But with two minis and an adventurous group it would be definitely be possible.