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.
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"! Click on our description of Lion's Head for directions and information about this unique spot. 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).
http://berkshirehiking.com/hikes/bearmt_salisbury.html
Mt. Frissell’s southwest shoulder is the highest point in Connecticut at 2,380 feet above sea level. It is one of only three US state highpoints that are the highest point in a state but not technically the summit of the hill or mountain. The easiest route to the summit, generally done from the AMC Parking next to the Massachusetts-Connecticut state line on Mt. Washington Road, is a very enjoyable hike with good views to be had on Round Mt., as well as the steeper sections of Mt. Frissell, including the state highpoint itself.
http://www.summitpost.org/mount-fris...houlder/152455