First Thing First:
You have a choice of any of the 3 major trailheads for this hike: the Garden, Adirondack Loj, or Upper Works
The Trip In A Nutshell:
We hiked in from the Upper Works trailhead via the Calamity Brook Trail (ADK #121, McM #39). From there we followed the Opalescent River Trail (ADK #121, McM #46) to the Uphill Brook lean-to at the intersection of Uphill Brook and the Opalescent River. This lean-to makes a very convenient "base camp" to hike the 5 peaks we had in mind. Our itinerary:
Day 1: Hike in from Upper Works to Uphill Brook lean-to.
Day 2: Climb Cliff and Redfield via their herd paths only a stone's throw away.
Day 3: Read, whittle, discuss the meaning of life, and pet the ranger's dog.
Day 4: Climb Gray Peak via its herd path which begins off the Feldspar Brook Trail at the outflow of Lake Tear-of-the-Clouds. Next climb Skylight and Marcy from Four Corners (the saddle between Skylight and Marcy; also the terminus of the Feldspar Brook Trail).
Day 5: Hike out to Upper Works
Marcy, the way we did it in conjunction with Skylight and Gray starting from the Uphill Brook lean-to, is an excellent moderate hike with lots of views and time to take photos. Compared to doing the Dixes in a day or the Santanonis, this ascent on Day Four of our trip was a walk in the park.
Marcy is easiest if you start from the Upper Works trailhead. Also, the parking at Upper Works is free unlike at the Garden or Adirondack Loj which are both quite expensive and crowded on weekends. Plus, the elevation of Upper Works enables you to start higher and, while its strenuous day hike, you will run into few people.
You'll be able to throw in Gray Peak as well since Gray is a "quickie" and barely a 20 minute detour from the Marcy trail.
For the description of the trails that we hiked in on, click here: Calamity Brook Trail, Opalescent River Trail, Feldspar Brook Trail, and Four
1. Feldspar Brook Trail to Four Corners
2. Four Corners to summit of Marcy
Map shows route from the Uphill lean-to on the Opalescent River to the summits of Gray, Skylight, and Marcy. The route shown is 4.5 miles from the lean-to to Gray, then Skylight, and then Marcy