Casey,
Are you currently in Weston, CT?? I've been through there before - used to live in CT ages ago. You have the Devil's Den Preserve right out your back door - 20 miles of trails that connect up to the 70+ miles of the Saugatuck Valley Trails System. I just took a quick look at the topo map, and while it's certainly not hiking in Colorado, there are several hundred feet of elevation changes around the Saugatuck Reservoir.
o5