Day 18

Sheridan, WY to Gillette, WY

• Miles: 108 mi

• Elevation Gain: 4,766 ft

Today’s Ride

Another big day! We rode 108 miles with 4,766 feet of climbing from Sheridan to Gillette, WY. After the massive effort of Big Horn Pass yesterday, today we leaned on our pace line to tick off the miles more efficiently.

The morning was beautiful rolling out of Sheridan, and we passed through several small towns along the way, including Ucross — population 26. The scenery was wide open, the roads stretched long, and we kept our heads down, focused on the finish.

It felt good to roll into Gillette by 3:30 p.m., with hopes of an early bedtime after two tough back-to-back days and another long one tomorrow!

Remembering My Friend Jessica
Gillette is the hometown of my best friend, Jessica, who was one of the biggest reasons I said yes to this cross-country adventure.

Jessica passed away in 2024 after a 12-year battle with a brain tumor. Through countless surgeries, rounds of chemo, and radiation, she lived her life with joy, positivity, and courage. She said yes to opportunities, laughed often, and never wasted a minute.

To be clear, Jessica would have thought I was crazy for doing this ride. But she also would have been my biggest cheerleader. Tonight, I honor her — her perspective, her zest for life, and her example that reminds me daily: don’t wait, live your life now to the fullest.

Tonight, I am exhausted but grateful. This ride continues to test me physically and emotionally, but moments like today remind me why I’m out here — to celebrate life, friendship, and the chance to see the world one pedal stroke at a time.

Our smiles say it all. Jessica lived with joy and laughter, and I’m so grateful to have shared so many moments like this with her.