Uncle's Around The Bend #20 & Trail Boss 250 Desert Challenge!

IYKYK. Watch this space! Please RSVP to stay in the loop! Venue, HQ, group dinner, lodging options, shirt & sticker designs and more to be added soon!

20th Annual Uncle’s Around the Bend rally.

1st ever Trail Boss 250 Desert Challenge - Become a Certified Trail Boss in Big Bend!

Mark your calendars: Uncle’s annual Around the Bend Motorcycle Rally & Trail Boss 250 Desert Challenge will be Feb 25-28, 2027 in Terlingua, Texas. This is the 20th year of the Uncle’s Around the Bend Rally and, as always, this event is open to everyone. It doesn’t matter if you are a street, dual sport, or ADV rider, there is plenty of great riding for all.

What kind of rally is this? It’s a motorcycle rally open to one and all. Street-only, adventure, and dual sport riders are all invited to attend. Come by yourself or bring some friends. Ride when you want and where you want. Have an adventure. Got a few extra days off? Then come on out early. Or stay a few days late. The main point is to have fun.

Street riders Do you ride street only? No problem, we have some great riding for you too. There are some awesome paved roads in the Big Bend area that really shouldn’t be missed. In fact, Hwy 170, aka “River Road” is one of the top 5 motorcycling roads in Texas.

Dual Sport and Adventure Riders Lots of dual sport riders enjoying riding the Big Bend desert. If you’ve always wanted to play in the dirt at Big Bend but just haven’t made it yet, this is a wonderful opportunity to do so. If you want something a little tougher then consider registering for the Trail Boss 250 Desert Challenge!

The Trail Boss 250 Desert Challenge, Friday, Feb 26th: The Trail Boss 250 Challenge is a 250 mile loop which includes sections of Terlingua Ranch and Big Bend National Park. Starting time and route to be published soon! Riders must complete the challenge in less than 12 hours to become a Certified Trail Boss.

NOTE: Trail Boss 250 Desert Challenge Riders will need to purchase a pass for Big Bend National Park. The majority of the Trail Boss 250 is held in Big Bend National Park and an entry permit is required. We strongly recommend getting your pass before Friday morning.

Please RSVP to stay in the loop with updates. Tickets to go on sale once itinerary is fully completed!