Hartford: Bear Mountain Loop

Tucked into a corner of the Taconic Mountains, this hardy 6.1-mile route hits the state's highest peak. Or is it second-highest? What the heck-climb both.
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Trail Facts

  • Distance: 7.7



Location: 42.0339889526367, -73.4281234741211

Head W on Undermountain Trail along stream and ponds


Location: 42.0341300964356, -73.4324798583984

L @ T; ascent begins


Location: 42.0311813354492, -73.4366607666016

R @ T along edge of steadily rising ridge


Location: 42.028148651123, -73.4458465576172

Head N for sharp ascent into ravine of Brassie Brook


Location: 42.030200958252, -73.4472122192383

R @ Y onto Paradise Lane Trail (built by AMC in 1954)


Location: 42.0392303466797, -73.4464797973633

Skirt Bear Mtn.'s E shoulder heading N; pass Paradise Lane Group Camping Area; keep N, crossing CT/MA state line twice. Caution: Watch for ratlesnakes


Location: 42.0497817993164, -73.4543533325195

Back in CT, go L @ T onto white-blazed AT for steep, 200-foot climb up Bear Mtn.'s S flank


Location: 42.0452919006348, -73.4542388916016

High views on Bear Mtn. (2,316 ft.). 1885 plaque on summit cairn dubs peak CT's highest. Technically, the S slope of nearby Mt. Frissel is 64 ft. taller, though the actual summit of Frissel is in MA. The debate continues among peakbaggers. Our solution: Climb Frissel on your next visit. Descend S down stony ledges dotted with scrub oak


Location: 42.0371513366699, -73.4567794799805

After descent, turn L @ T; route follows old Revolutionary War-era charcoal road


Location: 42.0348014831543, -73.4546890258789

Riga Junction: L @ Y back onto Undermountain Trail (blue blazes), closing loop in .7 mi. @ WPT 5; backtrack to car. Campers: Overnight @ Brassie Brook lean-to by staying on AT and hiking .5 mi. S to blue-blaze turnoff after brook crossing