Wintergreen Drive Bike Climb - PJAMM Cycling

Wintergreen Drive


All the cycling data and info you'll need to climb Wintergreen Drive

Page Contributor(s): John Summerson, The Complete Guide to Climbing (By Bike), 2nd Edition; Dan Razum, Campbel, CA, USA.

Explore this Climb

PJAMM Cycling LogoDark Sky logo



If you love climbing by bike and would like more detailed information on the world’s top bike climbs, join our PJAMM Cycling group and receive our Special Edition Climb Report.
  • Receive a monthly report.
  • Get detailed and entertaining information on the greatest bike climbs and climbing areas throughout the world.
  • Discover beautiful landscapes with drone video and professional photos of remote and exotic places.
  • Gain insider knowledge on where to stay and how to conquer some of the most difficult climbs.

Climb Summary

Cycling Wintergreen, Virginia - cyclist riding next to green sign for Wintergreen

Cycling Wintergreen to Devils Knob, Virginia.

Ride 7.2 miles gaining 2,903’ at 7.7% average grade.

This is the most difficult bike climb in Virginia. The climb starts about one mile up Route 664 from its T intersection with Route 151.  The first 3.2 miles (at 5.9%) of the climb are on Route 664 (a busy road), the next 3.5 miles are on Wintergreen Drive (at 9.4%), and the final half-mile is on Devils Knob Loop (at 8%).

Cycling Wintergreen, Virginia - PJAMM Adventure App shows climb grade and profile

Gradient profile as seen on the PJAMM Adventure App.

“The climb to Wintergreen is likely the most difficult in the state of Virginia and it is one of the most difficult in the Southeast United States.  Located in the central part of the state it is somewhat isolated but well worth the effort to get there.  Shallow to begin, the grade gradually increases as you ride along Route 664.  Through thick woods in places the grade gets steeper as you head west.  Scenery and little traffic most days creates a pleasant start to the ascent…” (This quote provided with the approval of John Summerson from his book The Complete Guide to Climbing (by Bike), 2nd Edition, pg. 120.)

Cycling Wintergreen, Virginia - first few miles of the climb along Route 664

First 3.2 miles are on Route 664 to the Wintergreen sign.

Cycling Wintergreen, Virginia - south fork of the Rockfish River along right of roadside at beginning of climb

During the first segment of the climb the South Fork of the Rockfish River is to our right.

Cycling Wintergreen, Virginia - bike parked in front of old large red barn along roadside

The first part of the climb is through a rural area.

Cycling Wintergreen, Virginia - large green side on roadside for Wintergreen

Turn right from Route 664 onto Wintergreen Drive at mile 3.2.

The steepest half-mile of the climb begins just before the turn onto Wintergreen Drive and is 12.5%.

Cycling Wintergreen, Virginia - photo collage, turn onto Devil's Knob Loop, PJAMM Cycling logo in corner

Be sure to turn left onto Devils Knob Loop at mile 6.7.

I missed the turn my first go at this one!

The following write up is by PJAMM’s Dan Razum of Campbell, California, USA:

The climb starts out gently alongside a creek. The gradient picks up and gets steeper near the cutoff to Wintergreen Drive (banner photo, above). After the cutoff the road enters a forest and there are some steep sections. There is a good view partway up, you can see the upper part of Route 664, above Wintergreen Drive, going up to Blue Ridge Parkway.  

Cycling Wintergreen, Virginia - views along two-lane roadway, surrounded by fall foliage, PJAMM Cycling logo in corner

Houses start to appear as you continue climbing, there is a fairly large community around the resort and ski area at the top of the mountain. About a mile before the top, Wintergreen Drive goes to the left in a short steep section.  However, you can bear to the right on Mountain Inn Loop if you want to avoid the steep section. Mountain Inn Loop comes around to meet
Wintergreen Drive again after the steep section.  More importantly however, there is a store on Mountain Inn Loop
where you can buy drinks and snacks and replenish water.

Back on Wintergreen Drive, a little ways after the store, there is an overlook with nice views of the valley
and the ski slopes. The overlook is midway through a steep section, so it is definitely tempting to stop and
take in the views.

Cycling Wintergreen, Virginia - bike parked at overlook at mile 6.4

Overlook at mile 6.4.

Shortly after the overlook you reach the high point of Wintergreen Drive.  However, it is not the top of the
mountain.  You can turn left and continue climbing on Devils Knob Loop for about a half a mile.

Cycling Wintergreen, Virginia - bike parked at various points and next to various road signs along climb route

The full climb ends at Devils Knob Loop and Fern Court.

Cycling Wintergreen, Virginia - two PJAMM Cyclists stand with bikes at climb finish next to tall trees on road side, fall foliage

Finish at Fern Court.

Cycling Wintergreen, Virginia - view from overlook past climb's finish overlooking Devils Knob

View for overlook past the finish on Devils Knob.

Route 664 and Blue Ridge Parkway are visible.

Bonus: Instead of returning the way you came, you can continue on Devils Knob Loop, which turns into Laurel
Springs Drive. Follow Laurel Springs Drive for about a mile and a half and there will be a small path on the
left. The path is just before a sign that says road ends in 0.5 mile. The path is not rideable, you have to walk
your bike over some stones and logs but after a couple hundred yards it comes out on Blue Ridge Parkway. You can
then ride Blue Ridge Parkway back to Route 664 and descend back to Route 151. If you can walk a couple hundred yards
in your bike shoes this little side trip is well worth it, there are some beautiful sweeping views along Blue
Ridge Parkway.

Traffic and Roadway Surface Report: The road surface is good throughout the entire ride, but there is little to no shoulder and a moderate amount of traffic, due to all the houses and condos around Wintergreen Resort.  However, the traffic we encountered was slow and courteous and the ride felt safe the whole way.