Bear Mountain (the tallest mountain in CT) and Mt. Frissell South Slope (its highest point, the place where the MA/CT line crosses Mt. Frissell whose peak is in MA) flank a dirt road that runs from South Egremont, MA to Salisbury, CT. The north end of this road is called the Mt. Washington Road and when it emerges in Salisbury, it is called the Mt. Riga Road; in the middle, at a tiny intersection by a diminutive church, it is called East Street. So many names for an obscure, 10-mile-long dirt road through the woods.
If you drive south from, say, the Stockbridge area, as given in the directions below, Bear will be on the East side of the road (to your left) and Frissell will be on the West (to your right). You will be able to see neither of them because of the trees. The trails for each start at the road, within 100 feet of each other, near an Appalachian Mountain Club (AMC) parking lot on the East (left) side of the road.
On September 23, 2005, the second day of Autumn that year, I drove down from Bascom Lodge at the summit of Mt. Greylock, the highest peak in MA. I was going to bag Mt. Frissell, Connecticut's highest point. After parking, I set off at a rapid pace and quickly reached the summit, only to be told (luckily) by another hiker that the mountain I had just climbed was not Mt. Frissell at all, but Bear Mountain.
So on that lovely fall day, I climbed two mountains (three, if you count Round, on the way to Frissell).
Bear Mountain is reached by going around the metal gate at the back of the AMC parking lot. You pass a large AMC sign up on a tree, warning you to behave yourself, and then by a small cabin to your right. After 1/2 mile or so, you come to an intersection. The trail ahead is flat, as is the trail to the left. To the right, the trail ascends through the trees up some natural stone steps, marked with the white AMC blaze; this is the way.
The trail is easy to follow but if you are in doubt, pause and look around for the white AMC blaze which may be on a tree to your left or it may be on the rock itself ahead of you or under your feet.
At the summit is a huge cairn built in 1885 by Owen Travis. It stands some 10 feet high or more, and as I climbed it I marveled at the huge effort that must have gone into its construction. The current structure is a reconstruction done in 1983 after years of deterioration; its current height is less than the original ... when you se it, you will agree that Owen was a prodigious mason.
The Mt. Frissell trail is found by turning right up the dirt road out of the AMC parking lot, back the way you came by my directions, past the stone pillar marking the MA/CT border on your right. On the left, 100 feet up the dirt road (or less) is the trail, marked with red blazes. This trail in parts is harder to follow than the Bear Mountain trail but the advice about pausing to look for blazes applies here, too, particularly blazes on the rocks which sometimes show not only the way, but a turn as well.
After the first scramble, you stand on a ridge, the top of Round Mountain. Bear Mountain is clearly visible behind you, and Mt. Frissell rises ahead of you across a small col or valley. You descend and then ascend, coming nearly to the summit. Straight ahead of you, unmarked, is the short trail to the summit proper with its log book strapped to a tree (in MA). To the left, as indicated by the red blaze on the rock, the trail leads you down and to the right, coming eventually to a small cairn and the green, circular metal marker showing the highest point in Connecticut.
I stayed the night at the White Hart Inn in Salisbury, CT. I can recommend both the Inn and the town as places to spend some time.
Directions to Bear Mountain and Mt. Frissell, CT, from the north
Take Rt 7 South past Great Barrington, MA
Take Rt 23 West to South Egremont, MA
Take Rt 41 South very briefly and then turn right onto the Mt. Washington Road
Go straight through the intersection of East Street and Cross Road (do not turn right to go to Bish Bash Falls State Park)
Past the Mt. Washington State Forest headquarters building on the right, the road goes from paved to dirt
Immediately after the MA/CT border marker on the left (a gray, 4-foot stone pillar nearly overgrown by the side of the road) is a small parking lot with an AMC sign. Park here.
Great views on a perfect clear day. As advertised, Steep! on some spots, but short. 2 hours round trip climbing.
Hiked to the highpoint of Connecticut and on to the top of Mount Frissell. Easy to get lost.
Not much of a summit, but a pleasant short hike with my friend Nerses.
I climbed this mountain as a convenient side trip while traveling from Syracuse to Worcester. I did not expect a whole lot from it, but I was pleasantly surprised. It took me a while just to find the trailhead, and once I found it and began my hike, I ran into some hikers returning and they said it was a 2-hour hike round-trip. However, I was in a hurry and I did it in 1 hour. I was pleasantly surprised with the many views from the open rocky summit of Round Mt., as well as the numverous views from Mt. Frissell. A nice hike indeed!