NW CT is my hiking stomping grounds, although I haven't gotten up there much the past few years (home life has been busy). Anyway, here are some of my standard routes:
- Undermountain --> AT --> Bear (up-and-back or down AT to Sages --> Paradise --> Under Mountain)
- Lion's Head to Bear via AT (rather long up-and-back [~8 miles?] but with a long flat section in the middle)
- Race Brook Falls to Race (up-and-back)
- South Taconic Trail to Alander (up-and-back)
- Prospect Mountain/Rand's View - AT (flat and easy)
It's a great area. Here are some images:
Alander Mountain - August 19, 2001
Mount Everett and Mount Race - December 10, 2000
Race Brook Falls - November 12, 2000
Prospect Mountain / Rand's View - November 5, 2000
Tri-State Loop - October 14/15, 2000
Bear Mountain - October 8, 2000
More
Alander Mountain - September 19, 1999
For Trip reports, see:
Bear & Round Mountains - October 12, 2001
Mount Washington State Forest / Riga Plateau - December 10, 2000
Mount Bear & Sages Ravine - October 24, 2000
Race Brook Falls/Mount Race - October 24, 1999
This truly is a wonderful area.