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Skyler Bolks Pedals into Summer with Clean Comedy, Gravel Roads, and a Whole Lot of Koozies

Skyler Bolks, the clean-cut comedian with a derailleur and a dream, just wrapped up a double-header weekend of laughter and lycra. Whether you caught him cracking wise at the Box Event Center in Box Elder or grabbing post-ride pints with RASDak riders at the Lost Cabin Beer Garden in Hill City, one thing’s clear: Skyler’s not just riding high—he’s gearing up for something big.

Box Elder Gets Box Seats

Saturday, Skyler performed his clean comedy show to a full house at the Box Event Center, delivering a tight, clean set for well over 200 comedy fans in the Rapid City area.

A night of comedy was followed up by pinball and arcade games as it often goes when Skyler is on the road. The customary shower beer was put on hold to keep his wit sharp and his quips quick for the next days adventure.

Hill City + RASDak = Spokes and Smiles

Sunday night kicked off in true two-wheeled style as Skyler brought cycling comedy to RASDak (Ride Across South Dakota) riders under the setting sun at Lost Cabin. In between stories about midwestern wind resistance and saddle-related soul searching, he previewed material from his upcoming 1,000-mile “Jokes and Spokes” Bicycle Comedy Tour, which launches this weekend.

Skyler’s no stranger to long-haul rides—he completed RAGBRAI last year and survived on a steady diet of granola bars, ice cream, and small-town root beers. Now, he’s diving deeper into the cycling scene, blending punchlines with pedals on a mission to become the face of gravel cycling humor (a surprisingly open market, it turns out).

And he wasn’t just pedaling jokes—he was spinning for a cause. Skyler pledged $150 from weekend koozie sales to support the Bike Park Project in Ogallala, proving he’s got just as much heart as handlebars.

“Jokes and Spokes” – Coming Soon to a Trailhead Near You

With the wheels officially turning, Skyler is in final prep for his “Jokes and Spokes” bike tour, a 1,000-mile ride that will combine live comedy shows with scenic routes, gravel cycling legs, and lots of awkward tan lines. The tour aims to highlight local bike communities, promote safe riding, and—of course—make people laugh wherever there’s a flat tire or flat beer.

Whether you’re in it for the humor or the handlebars, follow Skyler for updates, tour dates, and behind-the-scenes from the saddle. Because this summer, the road is long—but the jokes are tight.