In general, trails get progressively more difficult as you progress from east to west, with the most expert terrain, including some serious glades, on the top third of the mountain. Most trails are narrow, winding through birches and hardwoods and offering views of Saddleback Lake and the surrounding wilderness. From the summit (accessed via T-bar), you can gaze over the wind-stunted trees across the Rangeley Lakes to the Presidential Range and Mt. Washington.

Here's a larger, more detailed trail map.

Expert, Advanced: The upper-mountain Kennebago T-bar provides the only access to the steeps and glades off the summit, but it’s worth the aggravation to access the honest-to-goodness expert trails and take in the panoramic views. Do note: This is no place to learn to ride a T, it’s a bona fide double-black, often rutted and usually icy and with no place to go if you fall. Learn on the gentler Cupsuptic T, and don’t try this one until you’ve mastered it. Also  note: The jump from intermediate terrain to expert is big here. Get to the Kennebago T off the Rangeley double chair summit via Upper professor or Upper Peachy’s Peril to The Pass, a cat track that connects to the T-bar’s base. Off the T, begin with Tight Line, which is the only trail on the mountain cut wide and straight down the fall line. If you can’t handle this, you don’t belong up here. Dark Wizard is a tight glade. If you can handle that, move to the other side of the T and try Intimidator, Nightmare Glades or Thrombosis, all glades that earn their double-diamond rating. For an inbounds, back-country experience, skate and pole over Dazzler to Muleskinner, a truly au natural trail that gives a taste of the potential for developable terrain on the mountain’s west side. From the base of the T, Tight Line meanders back to the base lodge. [TOP]

Intermediate: The middle chunk of the mountain and all the terrain serviced by the Rangeley double chair is ideal for intermediates. Upper Green Weaver does what it promises, it weaves through the evergreens west off the chair. Red Devil, Blue Devil, Grey Ghost all dipsy doodle through the trees as do Lower Peachy’s Peril and Lower Professor. Leave the upper portions of those two natural snow trails to advanced skiers. The fun of Saddleback is the offshoots, such as Doodlebug, Muddler and others that meander through the woods. Also servicing much of this terrain is the Cupsuptic T-bar. [TOP]

Beginner, First-timer: The lower third, especially the new terrain below the base lodge, is designed for beginners. The gentle learning area with its own chairlift and choice of long trails attracts young families, first-timers and the not-yet confident. There’s even a beginner glade, Mrs. Duley. Once you’ve mastered turns and have some endurance, head to the summit and mosey down Hudson Highway, which edges the mountain’s eastern boundary. [TOP]