A passionate cyclist, hiker, and runner, Villaire is a regular contributor to the Backpacker magazine website and has written freelance articles on outdoor recreation for various publications, including Windy City Sports magazine, Silent Sports magazine, Rails to Trails magazine, The Chicago Tribune, and the Des Moines Register. He served as the editor of a weekly Chicago neighborhood newspaper and he worked for a number of years as a publications editor for a large, Chicago-based nonprofit. He has served with Illinois Leukemia and Lymphoma Society as a hiking leader for its Team in Training program. Villaire is the author of the book, 60 Hikes with 60 Miles: Chicago, published in its second edition in 2008. He also wrote the forthcoming books, Camping Illinois, Road Biking Illinois, and Best Bike Rides Near Chicago (FalconGuides).