Enjoy lightly traveled scenic country roads with a combination of flats, rolling hills, and climbs. The 67 and 100 routes travel along some streams, through covered bridges and beautiful country side.

If you like some hills, and want to train for the Annual Hilly Hundred ride, the Hilly 67 or 100 mile route is for YOU! You can even extend you route by just under 4 miles by adding the Optional Rail Fence (Hell Fence) hill, which is a continuous climb up!

Our most popular route is our 34 mile Lake Santee Route. While at the lake, enjoy traveling around the beautiful 6 mile Lake and then stop at our well-stocked SAG stop were you will find watermelon, and all kinds of fresh fruit and other goodies.

(New) this year, we have added a 50 mile route. This new route adds two different directions. The 1st half of the route goes to the Kingston area, back to town, and then the 2nd half travels to the town of Westport. Before returning to Greensburg, you'll travel through the historic Westport covered bridge, then back to town.

All routes except for the 16 and 50 travel around beautiful Lake Santee.

Music will be played at some of the SAG stops. All SAG stops are well stocked with refreshments and most have restrooms. All routes have SAG support to help keep riders safe. On your return, enjoy lunch with your choice of a grilled pork tenderloin or hamburger, side salads, dessert, drinks and more while listening to live music played from 11:30-2:30 or 3pm. If you would like a cold brew, there are various pubs on all sides of the square. All proceeds go to the YMCA's Annual Campaign.

Date: June 28, 2025
Distances: 16, 34, 50, 67, 100 miles
City, State: Greensburg, Indiana
Start Location: 150 Courthouse Square
Start Time: 7:00 am
Online Information: https://www.treecityrollingtour.org/
Email:
Phone: