There are multiple ability levels for SkiMeisters. Each ski day, the members separate into groups within these skiing levels. Some days, particularly Sundays, there may not be enough members to have all skiing levels so skiers will be divided into more informal groups.

The descriptions below delineate the ski trails used by each of the SkiMeisters levels.

Level 1: Discontinued.

Level 2: Discontinued.

Level 3: All green trails and all groomed blue trails.

Level 4: All level 3 trails.  All blue trails, all groomed blue/black and black trails, and the following small bump blue/black trails skied slowly:

• Winter Park and Vasquez Ridge trails: Jaberwocky, Cheshire Cat, JabberRabbit, Chuck Wagon, Engeldive, and (if one side is groomed) Bradley’s Bash,
• Mary Jane trails: Sleeper, Side Track, Sleepy Hollow, the top of Mary Jane, lower Rainbow Cut and (if one side is groomed) Railbender,
• Sunnyside trails: the bottom of Roundhouse,
• Parsenn Bowl trails: Larkspur, Sky Pilot, Fireberry Glade and Lupin.

Level 5: All level 4 trails.  All blue/black trails and the following medium bump black trails:

• Winter Park and Vasquez Ridge trails: all black trails,
• Mary Jane black trails: Gandy Dancer, Narrow Gauge, Sterling Way, Golden Spike, Upper Arrowhead Loop, Little Ten, Phantom Bridge, Railbender, Derailer and Grand Tour (a combination of Side Track and, cutting to the left at each segment, lower Upper Arrowhead Loop, the bottom of Golden Spike and the bottom of Gandy Dancer),
• Sunnyside: all Sunnyside trails,
• Parsenn Bowl trails: all Parsenn Bowl trails,
• Eagle Wind black trails: Thunderbird Traverse and Thunderbird trail.

Level 5+: All level 5 trails.  All black trails, including Eagle Wind and Vasquez Cirque; and the following tree areas not named on the trail map:

• High Lonesome trees: Tree area to right of High Lonesome and to the left of Whistlestop,
• Old man trees: Just to the right of the rope between Winter Park trails and Eagle Wind trails, accessed from the top of Parsenn Bowl or from Thunderbird Traverse and coming out onto Village Way trail,
• Wild Spur trees: Tree areas to left of Stagecoach; tree areas between Wild Spur trails; and tree areas to the right of Gambler, accessed from the Gunbarrel trail and coming out on Lonesome Whistle.

Level 6: All mountain with no restrictions, skiing with moderate speed and periodic stops.

Level 7: All mountain with no restrictions, skiing with high speed and no stops.

Your group may ski more advanced trails: Your group may ski one or more trails that are more advanced than the trails designated for your ski level, if most skiers in your group enthusiastically agree to do so. If you are not 100% comfortable skiing a more advanced trail for any reason, please tell your guide. If you or anyone else in your group tells your guide that they are not 100% comfortable skiing a more advanced trail, the group will not ski the more advanced trail, unless (1) your guide describes an easier trail that ends at the same lift as the more advanced trail; and (2) at least two skiers elect to ski the easier trail (at least two skiers because no one should ever ski alone).