The Naperville Rotary Ride hasn’t been the biggest or most elaborate on the suburban invitational bike ride calendar, but for nearly three decades now it’s taken bicyclists on great exurban roads and helped charities.
The 2026 edition started in a retail parking lot off the west end of Frontier Park in Naperville, then took 210 riders on roads again heading into Kendall County.
Those roads leave Will County to go west and south of Naperville, Aurora and Oswego, then by Yorkville and the small Fox River town of Millbrook. They’re a cyclist’s treat outside the suburban sprawl.
Plus the ride benefits children and families. The Rotary Ride since 1997 has been run by the Naperville Sunrise Rotary, one of four Rotary clubs in Naperville. The 35-year-old club that now has about 40 members, according to the Daily Herald, has made the ride one of its annual fundraisers.
The club says on its website that the 2026 Rotary Ride is contributing to the Grow Wellness Foundation for an in-school counseling program, Little Friends for family respite services, and the YMCA for an early childhood preschool scholarship program. It’s in keeping with the larger Rotary mission to help local organizations.
The route
The somewhat tightly spaced base of the ride happened to be not only by a Trek bike shop but also right by Will County’s Tall Grass Greenway Trail. And that’s where the ride began.
On a mostly out-and-back route with rest stops at about 11, 22 and 30 miles out, riders could choose their distances. A stop in Silver Springs State Park and a trip through Millbrook made the longest distance about 63 miles.
We all started on the Tall Grass Greenway west over Route 59, proceeded a couple of miles, then turned south onto the Normantown Trail, passing big homes’ mostly deluxe patios for a few miles. We finally got onto a road, 119th Street, after 5 miles.
Cyclists who live nearby and enjoy the roads in the country can guess what came next. We wended our way west on 119th-turned-Scotch Road, Stewart Road and Woolley Road into Oswego. The first and biggest rest stop came in Prairie Point Community Park.
Then we got to Grove Road and took it to the legendary Reservation Road. I call it legendary because over the years I’ve heard from cyclists about how pretty the road is. I can confirm both scenic open land and canopies of trees. (The road gets its name from bisecting two former American Indian reservations, or really reserves for one individual each, granted by the U.S. in the Treaty of 1829, according to longtime local historian Kevin Matile. Read more about Reservation Road separately.)
After that, we rode south on Minkler Road, jaunted about a half mile west on a somewhat difficult Route 126, turned south on cycling favorite Ashley Road (that goes all the way to Morris if you want), then west on Ament Road. A small rest stop was at a fairly random point on that road.
The long route then took us to a loop that included a rest stop near the entrance of Silver Springs — which offered quiet forest and Fox River scenery if we rode the park’s circular road — and then crossed the Fox. We rode Millhurst Road, then Whitfield Road back southeast across the Fox and into Millbrook.
It was disappointing not to ride Fox River Drive back northeast toward Silver Springs; the road doesn’t offer river views itself but still goes through pretty country. But the Rotary had us take Budd Road east to make a loop without repeating any roads — until we got back on the route on which we rode west. And back to the start we went, trails over the last 5 miles and everything.
Ride perks
The Rotary’s three rest stops were nothing fancy: no PB&J stations or baked goods or anything. The same things were offered at all three stops: bananas, oranges, packaged beef jerky, small packages of cookies and bars, and little packages of dried edamame.
Water coolers were provided, but more impressive was that protein drinks were offered, including a Starbucks caffeinated version. I hadn’t had a breakfast but could get fueled up fine at the 11th-mile rest stop; the snacks were offered at the ride start, too.
The bigger payoff came at the end when subway sandwiches and cheese, pepperoni and vegetarian pizza were supplied. It was Little Caesars pizza, but after 63 miles, we weren’t fussy.
The food was laid out on a few card tables in a section of the parking lot — no big tent or anything, so it looked pretty informal. And it behooved you to finish the ride early, because the Rotary volunteers were getting packed up by 2 p.m.
The crew certainly did its job with the road markings. They used simple, big, bright arrows both before turns and confirming after turns. The organizers put the routes on the Ride for GPS app, too, but you could have easily found your way with their arrows.
And the Rotary had at least a couple of sag vehicles along the route, with phone numbers provided ahead of time.
All in all, it’s impressive that this fairly small Rotary club put on this ride and made use of the great roads in the area. If you don’t need too much guidance, the Rotary Ride is worth doing.
• Do you find reviews and information like this valuable? This free website is made possible almost entirely by readers like you. Consider donating to help defray the costs of gathering and presenting this material.
