1. BEAR MOUNTAIN (easy route)
In Salisbury, turn north off Main Street/Route 44 at the Town Hall and drive up Factory Road/Washinee/Mount Riga Road to the ridge line at South Pond and Riga Lake where you turn right to drive the ridge. Not long after the turn, find a dirt road on the right. Park discretely nearby. (The South Taconic Trail Map 107 shows a dotted line marked Bear Mountain Road.) Or continue driving about a third of a mile to the small parking areas for Mt. Frissell and walk back. Simply hike this road until you see the Bear Mountain trail on the left. Through woods and ultimately an open field of low-bush blueberries, you’ll reach the peak in no time. Then either retrace your steps or—far better, if you don’t mind a small challenge— return the long way in a counterclockwise loop. The only hard part is right away when you must climb down a steep face of perhaps a hundred feet using hands and feet. Then you’ll be in a cool, open forest that’s quite magical. Continue around to the left, catch a small trail back up the mountain past a looming log lodge that belongs to the Appalachian Trail Club. Go left when you gain the road (or right if you parked at Mt. Frissell) and soon you’ll come across your car. A far more environmental approach is to walk the entire distance from and back to Salisbury, a full day of work and accomplishment. By the way, down to Salisbury and back by foot on this route is a recommended AT side trip for civilization-starved through-hikers.
2. BEAR MOUNTAIN via Undermountain Trail
Undermountain Trail starts three miles north of Salisbury off Route 41. There’s a dirt parking lot on the west side and during summer it’s easy to miss since it’s covered by foliage. Undermountain Trail might be the most popular trail in the state since it’s a jumping off point for a wide variety of hikes and is part of the Appalachian Trail. It rises sharply up for two pretty straight miles to meet the AT, which you join. From here it’s about another mile to the top of Bear Mountain with a short, semi-steep rise the final few hundred yards. This hike is about six miles round trip.
3. BEAR MOUNTAIN via Race Brook Falls
This popular option starts farther north, along the Salisbury-Egremont Road, Route 41 (turn north at the White Hart Inn). You must be in decent physical condition as this is a steep hike. But if you take your time and bring plenty of water and “energy food,” the whole experience will be well worth the effort. You’ll need to choose between the north and south sides of the stream. North will give you, in anything but a drought, a climb up to a tall, silvery string of a waterfall. The south trail breaks from the brook to flatten the ascent, then cuts back to cross the brook below a second waterfall, climbs sharply another 200 feet, walks for a mile or so along the trickle of a brook, and joins the Appalachian Trail. From here the daring or foolish continue on the AT to Mount Everett, at 2,602 the tallest peak in the Taconic range. Three AT lean-tos are nearby, attesting to this spot’s popularity. A bit north is Guilder Pond, rimmed by its own trail.
4. BEAR MOUNTAIN via Sages Ravine
Another difficult route so plan ahead. Find the parking lot on 41 to the west between Hammertown and Kelsey Roads. The trail meanders south a ways before finding the brook and ascending in parallel. About halfway up the AT joins from the south. Continue on the AT up to the road, or hang a left and a trail known as Paradise takes you to the upper base of Bear Mountain (see above). Meeting the Bear requires a good hundred feet of scrambling using all four appendages, so be careful and take your time.