Chicago, IL
The best riding I do is NOT LOCAL! The local trails have two-way singletrack and let me tell you that there is nothing worse than flying down a trail on a juiced Jekyll and running into oncomming traffic riding helmetless on a Huffy!
For great riding, I put the bike on the roof and head to Michigan--Fort Custer State park, for great riding and parental hospitality!
Cheers,
Tom