As the tallest peak in Connecticut (2,300 ft.) Bear Mountain has to be one of my favorite CT hikes…read more
There are several ways up to the summit, all of which are steep, long, and strenuous. On our most recent visit, we used Lion's Head. Although it's a bit longer than the Undermountain Trail, it's less vigorous and I think it has some really spectacular views. This is the perfect spot if you love panoramic overviews. From several lookouts, you can actually take in some great long-distance views. The southern part of Connecticut spreads out in front of you with the rolling Litchfield Hills to the south, Twin Lakes east, Massachusetts north-northeast, and surrounding mountainsides, farmland, woodlands, and small towns fill in the pieces of this picturesque puzzle (no western views). If you use Lion's head to reach the summit of Bear Mountain, it's a 6-mile round trip.
As you near the top, the Appalachian Trail appears and is marked with white hash marks whereas the Lion's Head trail is marked by blue hash marks. Keep this in mind for your return trip or you be going off course! FYI: Park at the dirt parking lot on Bunker Hill Rd on the labeled "hiker parking" lot.
All in all, the hike(s) up to Bear Mountain are tough and challenging even for the average day-hiker. With some patience, plenty of water and snacks, some determination and good company, Bear Mountain will be a great day-hike for any level. If you're feeling fancy, bring a bottle of wine and actual food and have a picnic at the summit. And if that still isn't enough, don't forget the journey's reward -- great overviews, Appalachian Trail access, title of hiking Connecticut's highest peaks, waterfalls, and woodlands.