Bear Mountain is the tallest “mountain” entirely within the state of Connecticut, located in Mt. Riga State Park. However, the tallest point in Connecticut is actually on the shoulder of Mt. Frissell. It is a fairly popular hike in Connecticut, and gives easy access to the Appalachian Trail. While not a strenuous climb by any stretch, it offers great views of New York, Massachussetts, and Connecticut. For the mountaineer who wants to bring the rest of the family on a trip into the woods, this is a good place to start. The grades are gentle to moderate, with only a short (few hundred feet) Class 1 rock scramble on the north side of the mountain.
There is a board detailing hiking and camping information at the trailhead, including a crude map of the area. There are no campfires allowed, and only camping at designated areas. From the parking lot you will follow Under Mountain Trail, and have a couple options in getting to the summit. The ideal route is to take the Paradise Lane Trail, which is the first trail on your right a little over a mile from the trailhead. Continue on this trail, going past Paradise 
Campground which is approximately 2 miles from the parking lot. Continue on, passing through a bog/swamp, until you reach the Appalachian Trail, which is marked with white blazes. Turn left and follow the blazes, leading up to the north side of the mountain. Here you will make your way up a fairly easy rock scramble, and on to the summit.
The summit has a large pile of rocks, which makes viewing the surrounding valleys much easier. To descend, continue south on the Appalachian Trail, until you reach the Riga junction, in which the Under Mountain Trail comes in on your left. Take the Under Mountain Trail back to the parking lot. Round trip mileage is approximately 6.7 miles.
Climbing in the winter depends on the conditions. It can be bone dry, or a few feet of snow on the ground, depending on the snow season. Traffic in the winter is usually substantially less than in the summer, so if there is a lot of snow, you may wish to consider snowshoes. Crampons really aren’t necessary, but if the trail is well-trodden, it can get icy in sections. As long as you have at least trekking poles, you should fare ok.
Getting There
Take Route 44 to Salisbury, CT. In Salisbury, take Route 41 North. If you are coming from Massachussetts, take Route 41 South The hiker parking lot is on the left side of the road approximately 3 miles up. Coming from MA, it’s on the right. In the summer, the lot can fill up, especially on the weekends….get there early to get a good spot (or a spot in the lot itself). The lot is marked by a blue sign denoting the Undermountain Trailhead.
When To Hike
Most people climb in the spring, summer, and fall….however, winter climbs can be enjoyable. For novice hikers just starting out in mountaineering, a hike in a good winter storm would be good practice, as it’s pretty much impossible to get lost.
Source: Summit Post
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