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Bear Mountain in Salisbury has the tallest peak in the state of Connecticut at 2,316 feet (the highest point in Connecticut is 2,380 feet on a mountainside of Mt. Frissel whose peak is in Massachusetts). There are a few ways to get to the top and all of them fall under the strenuous category (BerkshireHiking.com is geared towards the day-hiker so if you're a hard-core hiker this would be a great workout but probably wouldn't fall under strenuous for you). You must be in decent physical condition to attempt Bear Mountain. It's a long hike and steep. But if you take your time and bring plenty of water and "energy food" the views from Bear Mountain are breathtaking and well worth the effort.
The most logical way to climb up to Bear Mountain would be to take Undermountain Trail which is 3 miles north of Salisbury off of Route 41. (There's a dirt parking lot on the left hand side and during summer months it's easy to drive right past it since it's covered up by trees and bushes.) 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. Because of this the trail is well maintained and clearly marked. Undermountain Trail is steep as it rises straight up for 2 miles where it meets up with the Appalachian Trial. There's no easing into the hike here! It gets your heart pumping straight off. When you reach the large wooden trail sign as Undermountain and Appalachian Trails meet, you'll take a right turn onto the Appalachian Trail. From here it's about another mile to the top of Bear Mountain with a short, semi-steep rise the final few hundred yards. An old stone tower remains (really just a large piles of rocks neatly arranged) and when you scramble up, you're rewarded for your efforts. Hike up here on a clear day and you'll be impressed and refreshed! This hike is about 5-6 miles round trip.
Another option to Bear Mountain is to start at Lion's Head and follow the Appalachian Trail over to Bear Mountain. This route is a little longer than Undermountain Trail option but is probably a little less strenuous...although either route is challenging. Lion's Head is a spectacular sight in and of itself. Incorporate Bear Mountain and you'll earn the title of "hardcore hiker"! Once you've hike up the short but steep trail to Lion's Head, take in the spectacular views and fuel up. Then head north on the Appalachian Trail, marked with white paint on tree trunks. A few hundred yards up from Lion's Head is a nice open plateau with a beautiful view of distant mountains and lush forest (You'll also hear the distant rumble of a waterfall but don't venture down the mountain side with it's thick growth in hopes of seeing the waterfall. It's not as close as it sounds and potentially a dangerous thing to do).
Keep going along the Appalachian Trail as it makes it way through thick woodlands, over streams/small waterfalls, past marshy areas, and on up towards Bear Mountain. If you're there during mid-June to July, white and pink mountain laurel explodes throughout this region and is quite a site to behold. Along the way you'll pass overnight campgrounds and shelters. The Riga campsite is a good place to get some fresh mountain spring water. Never drink from a stream or river no matter how clean it may seem...use the water spout available at the campground. At Riga you can take in some nice views of the valley below from the wooden shelter area. After the pit stop here, venture on towards Bear Mountain (This is also a good place to decide if you want to keep going or would like to call it a day and try Bear Mountain some other time. If you're already tired it wouldn't be wise to continue on). It's still a good little hike to Bear Mountain but the terrain is very manageable from Riga campsite. Remember, by driving up the steep road to Lion's Head and then climbing Lion's Head you've already taken care of a lot of the steep part...there's just a short semi-steep climb the last few hundreds at Bear Mountain. After you've taken in the spectacular views at Bear Mountain just turn around and follow the Appalachian Trail back to Lion's Head and your car. An extra benefit of this trail option is that you'll take in the views at Lion's Head again before heading back to your car.
All in all, the hike(s) up to Bear Mountain are tough ones for the average day-hiker but you don't have to be in world class shape to attempt it. With a little patience, plenty of water and snacks, and determination, the rewards far outweigh the strains of climbing up the tallest peak in Connecticut. And you'll be proud and happy you did!