While staying at my sister's on vacation, I was able to find this nearby park and get three days of fine trailrunning in on this loop. The East Esker Trail, according to the write-up on the map, (get one at the Park Office), is a challenging 4.7 mile trail. Looking at the map, it is also the longest trail and has several rolling hills as you would expect with an esker. What is an esker? Click here to find out: Esker. I use to run on an esker trail when I lived in Massachusetts, so I knew this would be a fun but tough trail. With eskers, I usually expect continual rollers, and the feeling that I am high up in the hills/mountains, even when I am not.
The East Esker Trail, starting from the little parking area near the junction of Douglas and Pond Road, (just south of the Calvary Lodge) and heading in a counter-clockwise direction, begins by going up a short hill and then leveling out. Eventually it deposits you out near another trailhead entrance/parking area for this same loop. Just before I got there, as the trees opened up, near a small prairie on top of a knoll, I saw the same bunny rabbit sitting by the trail every day! I think he/she must've lived nearby! It's pretty funny, because that is the only rabbit I saw the whole time I was there, while I counted 30-50+ deer everyday between my driving and running through the park! Sometimes I almost had to shoe the deer off the route.
Anyway, after the bunny, the trail turns North and goes back uphill again. There are several hills in this first mile, making it the hardest of the 4-5 mile loop. (BTW, once you figure out the main loop and where you are, route finding is pretty easy.) The second mile is not much easier, but once you hit the water tower and start coming back down, (around 2.4?) the second half of the run is where you can make some time back up on the downhills and flats. This half has a few portions of nice single-track as well as double-track and skirts a pond for part of it. The second half is not without hills, but it seems like there are less than the first half.
Most of this whole route is tree covered, so with the high humidity we had that week, I was pretty wet afterwards, though there's little problem with sun. Also, wear a hat, because the greenheads/horseflies/whatever they were, go for your head, totally annoying, and sometimes biting. A visor the second day meant I was continually being attacked up top, whereas a cap the other two days seemed to help lessen the issue.
Double loops were fun, but tiring. The family mini-van was a great aid-station. The park is something like 2500 acres and has all types of other trails, a playground, and various ponds. So it could be totally possible to make your outing family friendly with lots of things for the kids and other non-runners to do.