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Cliffhanger Challenge

Saturday & Sunday, May 23-24

Part of the Blues, Brews & BBQ Festival over Memorial Day Weekend 2015, join us for the Cliffhanger Challenge Mountain Bike Race &Trail Run at Wintergreen Resort!

Memorial Day Lodging Special

Come for the race, stay for the party -- we'll have the Blues, Brews & BBQ Festival featuring live blues music, a micro-brew festival, an arts & craft fair, block party, and a day at the Lake - Lake Monocan opens for the season!  This year, if you book early you can take advantage of our special lodging offer with rates starting at $119! Rates are per room, per night; 2-night minimum; other restrictions may apply. Check availability now!

Mountain Bike Race

Part of the Virginia Off Road Series, the race will be cross-country with laps about six miles in length. Three experience levels will be offered: Beginner racer - one lap; Sport Racer - two laps; Expert Racer - 3 laps. The course will travel through Wintergreen’s ski terrain from Acorn to Highlands providing plenty of challenging elevation changes.


Sign up early for discounted entry fees. All entrants will receive a cool wicking t-shirt. Register online at


The Cliffhanger Challenge takes its name from one of our black diamond ski runs -- The Cliffhanger. The race course meanders up this wicked slope as you can see on the Wintergreen Resort Mountain Biking Trail Map. The mountain biking trail will be open to pre-ride as soon as all our great SNOWPOWER snow melts away. For more information, see Mountain Biking at Wintergreen Resort.


  • Pre-Ride Saturday, May 23 11 am-4 pm
  • Race Day Registration Sunday, May 24 9:30-11 am, Blue Ridge Terrace
  • Race Start Sunday, May 24
    • Expert (three laps): 12 pm
    • Sport (two laps): 12 pm
    • Beginner (one lap): 12 pm
  • Race Awards: Sunday, May 24, 4 pm, Blue Ridge Terrace


Prizes will consist of gift certificates, lift tickets, tubing tickets and recreation tickets for use at Wintergreen Resort. An additional cash prize will be awarded to the top male and female in the expert category.

  • Beginner: by age groups, men’s/women’s;
  • Sport: by age groups, men’s/women’s;
  • Expert: by age groups, men’s/women’s.

Trail Run

Join us for the 1st annual Cliffhanger Challenge Trail Run, part of the Cliffhanger Challenge weekend, featuring the Blues, Brews & BBQ. The 7K course will travel from Acorn to Highlands providing plenty of challenging elevation changes. There are one and two lap divisions based on age and gender. Proceeds help support the Wintergreen Nature Foundation.


Sign up early for discounted entry fees. Prices increase May 1. High performance t-shirt for first 100 entrants included. Register online at


  • Friday, May 22
    • Course marked for pre-runs
  • Saturday, May 23
    • 7 - 8 am: Runner check-in and day of Registration
    • 9 am: Mass Start
    • 12:30 pm: Awards


1st place prize for all divisions.