Cherohala Challenge

Sat June 3, 2023 Tellico Plains, TN 37385 US Directions


225 Cherohala Skyway
Tellico Plains, TN US 37385


The Smoky Mountain Wheelmen proudly present the 21st Edition of the Cherohala Challenge.

The 2023 Date is JUNE 3!

The event offers three distinctive rides that almost anyone can find a ride that will fit their skill level with rides of  35, 62, and 115 miles. 

Join us Saturday, June 3rd, for breathtaking views and pride inducing climbs on one of three world class routes.

Options begin with a new loop 35 mile route taking you through scenic valleys and rolling hills with only 1,900 feet of climbing. This new ride is a great addition to the day.

The more adventurous will want to tackle the Metric Century. Boasting 8,200ft over a total of 63 miles, this up and back route guides you to the top of the Skyway and then lets you turn around and coast your way back down the mountain you just conquered.

The title event, the Cherohala Challenge Century, is not for the faint of heart. This once in a lifetime ride tests riders with 115 miles and 10,350ft of climbing across two states. Riders begin in Tellico Plains heading north to climb to Deals Gap and brave the fabled 318 curves of the Tail of the Dragon. After besting the beast, riders will descend the mountain into the Joyce Kilmer Forest near Robbinsville, North Carolina. What goes down must come up and riders begin their ascent across the magnificent Cherohala Skyway. As a reward, the final stretch is almost all down hill, finishing to an outstanding post ride meal. 

And keeping with tradition, DRAGON SLAYER medals will go to all who conquer the beast in 7 hours or less.

No Knight is complete without their retinue so the ride provides you with a staggering amount of support. Experienced SAG vehicles are joined by moto support, mechanics, amazing rest stop crews, and friendly staff.

The Wheelmen are proud of our legacy and want you to come experience one of the Southeast’s premier rides!  Start training now to SLAY THE DRAGON!

  • All routes are fully SAG supported with well-stocked rest stops. 
  • Free post-ride meal. 
  • All riders must wear helmets.
  • Custom Event T-shirt for all riders who preregister.
  • Custom cycling kit available to purchase now through June 12th with kits estimated to ship by July 28th.

Packet pickup info:
Packet pickup from 3-6pm at LeMond Bicycles on Thursday June 1. Address is 10351 Deerborn Lane, Knoxville, TN 37932
Packet pickup 4-8pm on Friday June 2 at Visitor Center and 5:30-6:50 am on June 3 at Visitor Center in Tellico Plains. Address is 225 Cherohala Skyway, Tellico Plains, TN 37385

Ride start time
115 mile - 7:00am
62 mile - 7:10am
35 mile - 7:20am


Skyway Cycling Festival

Through partnerships with Cherohala Cycles, the Town of Tellico Plains, and Monroe County Tourism, we are proud to announce the Skyway Cycling Festival. The festival kicks off on Friday night with pre-registration package pick up, music, and food vendors at the Tellico Plains Visitor Center.  

The Festival continues on Saturday, June 3, 2023 from 10 a.m. to 3 p.m. in Downtown Tellico Plains. On Saturday the festival will host vendors, food trucks, cycling specialists, and more, while also promoting safe cycling skills and driver, cyclists, pedestrian safety.

This addition will assist us in expanding the Cherohala Challenge to a true family event that everyone can enjoy while supporting their favorite cyclist.

For more information, check out the Cycling Fest Website


Route Information

All riders get full digital maps and turn by turn directions through Ride With GPS.
If you don't have an account already, you will only need to make a FREE account. The paid level of benefits comes free to all riders who connect their accounts to the event using the link below.



Race Contact Info

If you have any questions about this race, click the button below.



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