UPDATE: As of June 1, 2025, there are many roads & detours due to construction within Jefferson & neighboring counties that may impact your ride on the Serpent. Please check out our Travel Updates page to stay informed before starting your journey!

The ride starts and ends in Madison, Indiana, enjoyed by thousands every year as one of America’s great weekend getaway towns. It’s also known as Indiana’s Music City, so there’s plenty to do and see when you roll back into town after a day on the roads.

The route goes through several other quaint Indiana towns where a weary traveler can enjoy a little relaxation before heading back out. These include Friendship, Rising Sun and Vevay. Generally speaking, if you take breaks in these towns and travel at a moderate pace, the Serpent will take about 4 hours to complete.

All the roads are well paved and well-marked, although the pavement on hillsides and near the river is prone to sliding and getting a little bumpy, so keep your wits about you and don’t exceed your limits. The “Snake” can bite if you’re not careful!