Open roads, rolling hills, and varied terrain - just outside your front door!
Cycling in the Driftless is challenging for even the most accomplished rider, and we can help you craft the perfect experience with your goals and current conditions in mind. Quality cycling and quality time are closer than you think.
Galena, Elizabeth, Stockton, and beyond..
Our charming communities are home to welcoming shops, cafes, and accommodations: creature comforts perfect for riders and their biggest fans. Whenever possible, we incorporate town visits, historic sites, and attractions into ride plans.
Learn more about visiting Jo Daviess County from our friends at Galena Country Tourism.
Your Guide
Originally from Chicago, James began cycling the Driftless on day-trips that started before dawn and never lasted long enough. He moved to the countryside near historic Galena, Illinois in 2020, creating and mapping area routes as a hobby.
With an encyclopedic knowledge of local roads and trails, and a desire to help more people find similar joy, he has organized rides for individuals and groups of all abilities. He believes cycling offers a powerful connection to the environment, our history, and ourselves.
James is a real estate agent and active volunteer in his community. He also enjoys collecting antiques and traveling with his wife.
