The Indian Pass trail was easily the best/most interesting lead-in trail we’ve taken. It’s much prettier (and softer) than the Van Hoevenberg or Phelps trails, and not nearly as boring as Lake Road.
Many (most?) people choose to climb Cliff & Redfield Mountains from the south via the Upper Works trailhead. From the Adirondack Loj, where Kathy and I started, the mileage is about the same, but our route skirts the 3,800-foot elevation Lake Arnold, adding several hundred feet of climbing both ways.