Winter Park Resort to 5 Points

Some prefer to challenge themselves by climbing, then savor the reward of the descent. This ride meets those goals!

Begin at the Winter Park Base and ride up Turnpike at the north end of the ski area. Turn left on Long Trail. Long Trail is a single track that will climb somewhat aggressively at times while working through the woods and across an occasional ski run and road. Climb up Long Trail to 300 Yard Walk (dirt road). Cross 300 Yard Walk and continue on Long Trail (trail on your left). Cross the service road, or Turnpike, and pick up Long Trail yet again, riding behind the Eskimo chairlift. Cross the road again. Climb through the woods, up switchbacks to the service road, cross the road to Long Trail. At this point, the trail starts crisscrossing ski trails near the Prospector lift. The single track will end at a service road. Head slightly downhill to the 5 Points Intersection. At the 5 Points Intersection, you are through climbing on Long Trail and can savor your reward, a long single track descent.

Turn right at the 5 Points Intersection. Take the next right to Upper Arapaho. Watch your speed, as there are many “whoop de do’s” and a few tight turns.

At the end of Upper Arapaho you will come to a ski-area service road. Cross the road to Lower Arapaho. Lower Arapaho will be the hardest part of your ride. Climbing a bit at first, the trail winds and travels through pine forest. As it flattens, get ready for a challenging descent. Sharp tight switchbacks, rock terrain and a very narrow trail will keep you alert and test your skills. Lower Arapaho will exit onto Upper Cherokee.           

To return to Winter Park Resort Base via Long Trail, turn right at the intersection (not marked) and left onto Long Trail (see route 4 for details). Descend Upper Cherokee. This is, at first, a somewhat technical trail that becomes a very narrow, slightly downhill, higher-speed single track. Canopied with trees, the feeling is very tunnel like. Upper Cherokee will end at Tunnel Hill (a dirt road). Turn right, then left onto Lower Cherokee. Lower Cherokee can be a very fast two track. Watch your speed and don’t exceed your skill level. This two track has enough large sharp rocks that flat tires are very common, yet this is one of the more popular cross-country descents and a favorite with racers. Lower Cherokee will exit onto Tracks Trail. Take a sharp right on Tracks Trail, then right on Serenity. Serenity is a narrow single-track climb through the pines. Although you are very near town and the railroad tracks, you will feel as if you are miles away from civilization. Serenity will exit onto Tracks Trail. Turn right on Tracks Trail, cross the road and continue to follow the train tracks back to Winter Park Resort Base.