If your perfect summer weekend includes crisp mountain air, a bike, and a challenge worth pedaling for, mark your calendar for August 2, 2025. That’s when Crooked Gravel Bike Ride kicks off Crooked Weekend in Winter Park, Colorado, with scenic routes, epic climbs, and the kind of scenery that makes you forget you’re in the middle of a race.
Hosted at the Rendezvous Event Center, this annual event brings gravel riders from all over to experience what Colorado does best—wide-open views, fresh trails, and a whole lot of altitude. Whether you’re pushing for a personal record or cruising for the views, this ride gives you a front-row seat to everything that makes Winter Park a favorite for cyclists.
A Course That Pushes and Inspires
The event features two main routes: a short course and a long course. Both start with a neutral, police-led rollout down Main Street, giving participants a high-energy sendoff before hitting the open gravel.
The short course covers 25 miles of rolling terrain—enough to get your heart pumping, but still perfect for casual riders or anyone looking to ease into gravel riding. With wildflowers lining the road, aspen groves flickering in the breeze, and the sound of brooks along the way, every mile feels worth it.
The long course is built for those who want to go all in. It offers more miles, more elevation, and more reward. Riders climb to over 10,500 feet and tackle a 12-mile sustained incline that defines what it means to earn the view. It’s a true test of strength, grit, and endurance—but the landscape pays you back tenfold.
You don’t have to be a pro. You just have to love the ride.
More Than a Race—It’s a Weekend
Crooked Weekend isn’t just for riders. It’s a gathering of friends, families, and fans of the outdoors. There’s a buzz in town all weekend, with visitors filling shops, restaurants, and sidewalks. The event closes with live music by Puddle Stomp, turning the finish line into a celebration that goes beyond medals and finish times.
There’s also the Crooked Gravel Run on Sunday, August 3. So even if you don’t ride, there’s a reason to stick around and soak it all in.
Everything starts and ends downtown, which means you can walk to the start line, meet friends for a beer after, or grab dinner without moving your car. That’s the beauty of Winter Park—it’s built for weekends like this.
Rest Easy After the Ride
After logging that many miles and climbing that much elevation, you’ll want more than just a place to crash. You’ll want a space to recover.
The Jabberwocky offers just that. Our mountain home is calm, cozy, and just minutes from the Rendezvous Event Center. It’s where you can come back, stretch out, and enjoy the kind of peace you won’t find in a hotel lobby.
Take a long shower. Rest your legs. Cook something satisfying in a real kitchen. Then step out onto the deck and breathe in the evening without the buzz of the crowd. That’s what staying right feels like.
We’re close enough to walk downtown, but far enough to sleep quietly. And for riders looking to make it a full weekend, this is where the recovery starts.
Make It a Ride to Remember
The Crooked Gravel Bike Ride is one of those events that gives you a real sense of place. Not just the challenge of the ride, but the feel of the town, the welcome from the locals, and the memory of crossing the finish line with dust on your face and a story to tell.
If you’re coming for the ride, don’t make it a quick trip. Make it a weekend.
👉 Book your stay at The Jabberwocky now and give yourself the space to ride, recover, and enjoy everything Winter Park has to offer.
