When you hear “36 miles,” it might sound like a casual ride, unless you’re in the Ozarks. One of my earliest cycling adventures in Bentonville came in January 2024, when I signed up for The Rule of 3.99, a ride benefiting Pedal It Forward and the precursor for the big race in May, The Rule of Three. I thought it would be easy cruising with a friend I’d met soon after moving here. Instead, the relentless punchy climbs and challenging terrain turned it into an unforgettable test of grit—and a ride I’ll never forget.

 

Why I Signed Up for the Rule of 3.99 Short Route

I've always loved the alt-biking vibe, so this ride felt like the perfect way to dive into the trails of my new home. The idea of tackling tarmac, gravel, and singletrack, all on one bike, was irresistible. So, I went for the “Short Route,” roughly 40 miles, starting and ending at Bike Rack Brewing Co. in Bentonville.

A Hard, Cold, and Unique Ride 

The rollout of town was pure joy. My riding partner and I (along with 700 other cyclists) cruised along the Razorback Greenway heading north toward Slaughter Pen, then bombed down the ever-thrilling J Street before hitting Price Coffee Road—a stretch of gravel beloved by locals and a staple for pros in the Life Time Big Sugar Gravel race.

 

Next came one of the coolest features of gravel riding in Northwest Arkansas: the gravel connectors! These purpose-built trails link different parts of the region without forcing you onto major roads, and they’re a game-changer for exploring. It was about then that I realized I might be a little underdressed—and maybe underbiked—for a day that “felt like 29.” The soggy gravel clinging to my tires didn’t help either; it was like pedaling through sticky glue. Thankfully, I was riding with a true local whose guidance and encouragement kept me rolling as I slid around corners and started to understand why gravel riding here has such a devoted following.

 

Muddy bicycles at the rule of 3.99Mers' bicycle caked in mud

 

This ride doesn’t come without fun; halfway through the route we had one of the best aide stations I’ve ever encountered: one fully stocked with not only snacks but a hot mobile sauna for this very cold and blustery day. Did I mention the wind picked up from the north? Yeah, downright bone chilling. 

 

The warm-up was welcome because the next stretch took us onto singletrack. We climbed Pinion Creek, snaked over to Mormon Trail, and connected to the Back 40 system—just as the rain started spitting and faster riders from the long loop crossed our path. I did my best to stay clear, and they did their best to stay friendly despite the cold and burning legs.

 

Under the highway—yes, there are dedicated bike tunnels here—I realized my riding partner was in a different league. While I huffed up 13% grades on a bike not built for singletrack, he casually chatted along Tavistock Canyon. His hardtail choice suddenly made perfect sense. From there, we dropped into Down Under, a chip-and-seal descent that’s pure joy: flowy turns and a holler at the bottom. By the end, with frozen hands and fried legs, we skipped the last few miles of singletrack. Thankfully, Bentonville’s bike lanes made the ride back easy. The free beverage for riders at Bike Rack Brewing Co. was well earned.

From Mud to Pure Joy

Looking back, my Strava title still says it best: Rule of 3.99—hard, cold, and my back hurts. Oh, and very muddy. But now, I see it differently. What an incredible introduction to Northwest Arkansas. The longer I’ve lived here, the more I appreciate rides like this—where you can link tarmac, gravel, and singletrack into one epic adventure. That mix doesn’t happen just anywhere; it’s something you can only experience here in Bentonville. Add in a few gear upgrades, and these rides have become some of my absolute favorites.

 

Plan Your Cycling Experience

If you’re ready to ride in Bentonville, but not quite ready to tackle the Rule of 3.99 (or the Rule of Three), check out these other super fun curated routes: