An organized bike ride on the pretty open roads of McHenry County was an annual event put on by the McHenry County Bicycle Club. But when the club could no longer do it, Trudy Wakeman took it over.
Now the McHenry County Century Ride is one of the events put on by Race Production By Trudy.
Wakeman’s company puts on other running, cycling and triathlon events, too. And she often does it for charity.
The Century Ride is a fundraiser, just from the entry fees, for the Lake in the Hills People for Parks Foundation. It helps “financially back programs for residents who may not be able to afford” park programs, according to the ride’s web page. “This in itself enhances the lives of children with the sole purpose of play, social interaction, arts, and a variety of benefits that can last a lifetime.”
Wakeman is just the one to run it. She is the former director of parks and recreation in Lake in the Hills, and she’s been a triathlete herself up to the Ironman level. “This is my retirement now,” she told me.
The ride’s views
The McHenry County Century Ride really can be any length you want, from 15 to 101 miles. It starts at Sunset Park in northwest Lake in the Hills — on the edge of suburban Chicago sprawl, meaning country roads are close at hand.
If you know McHenry County roads, you know they’re a sort of an Intro to Wisconsin. It’s certainly farm country, but as the terrain gets hillier the farther north you go, the scenery gets prettier.
Especially in the spring, it’s awfully green — yes, there are trees here and there.
So that’s what you’ll see on this ride. The one required route ran 14 miles out of Sunset Park and the last bit out of Lake in the Hills, via trails or roads.
But soon enough we were on the country roads headed to Union, home of the Illinois Railway Museum and, for 43 years anyway, Donley’s Wild West Town.
The roads were mostly lightly trafficked, but the routes did sometimes take us on busier, striped roads and we had to stay single-file. That makes this ride best for serious cyclists and casual bicyclists, less so for families.
We didn’t make tourist stops in Union; instead we had a rest stop at a little shelter off Park Street. That served as the hub for the remaining loops.
The routes
Four loops were created for 2026, named after key roads. The “Becks” route was about 14 miles out southwest. The “Harmony” route was 21 miles out west.
The “Garden Valley” route was about a 15-mile square to the northeast. And the “Deerpass” route is a figure-eight pair of loops to the north.
All the routes were available for download in the Ride for GPS app. Plus 50-, 63- and 101-mile routes were assembled, with the latter combining all the loops.
I did the metric-century route, which included the Becks and Deerpass route. Metric riders could have selected the Harmony route instead of Deerpass to make their distance.
Deerpass Road turned out to be the hardest road for me. It was just a 2-mile stretch lining the west side of one of the two loops within the loop, but it was the most prominent roller on my ride, and we happened to take it north against the wind.
That’s the thing about riding in the country, you know: You’re subject to the whims of the wind. For this ride in 2026, the north-northwest breeze wasn’t too bad, and actually it provided a big boost on the way back east and south to Sunset Park.
A professional ride
No matter which route anyone chose, there should have been no problem following the directions on the road. Wakeman employed professional route markers, with the colored rectangular arrows, and yellow signs with big black arrows were inserted into the ground at intersections.
Wakeman also got help from two nonprofits and other volunteers to assemble the rest stop and drive SAG vehicles.
The rest stop was well-stocked with PB&J sandwiches (handmade, not the packaged stuff), berries and bananas, cookies and bags of chips, plus pickle juice, Gatorade and water. A few portable restrooms were available, no big waiting.
At the end in Sunset Park, Wakeman provided pinwheel sandwiches as well as more cookies and chips. The park offered plenty of space to park and get ready, and it wasn’t hard to drive to — only far if you’re coming from nearer suburbs.
Thorough web and registration pages, and regular emails from Trudy before the ride (and even the morning of to warn us to wait out a thunderstorm) rounded out a pretty professional-level operation.
All in all, the “Century Ride” was a lovely way to sample the McHenry County roads around Lake in the Hills and Union.
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