I hiked this mountain on October 18, 2024. I hiked Bear Mountain trail. Bear mountain did not disappoint. The fall foliage was beautiful. So many yellows and oranges. The was one little fly that we seem to make friends with. The scrabbles were good and a nice mix up to the trail. The trail was well marked and maintained. We were able to stand on the CT/MA line. The trail was about 6.5 miles long. read more

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As the tallest peak in Connecticut (2,300 ft.) Bear Mountain has to be one of my favorite CT hikes. 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. read more

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I skipped Lion's Head to take on the Under Mountain trail. No regrets. This is a good step up from Ragged Mountain. 1. Parking located off Rte 41 N on the left coming from 44 2. Took a photo of the map on the bulletin board to avoid confusion on the hike and stay on track towards Bear Mountain peak - took me 90 mins 3. Bring drinks and snacks. This hike is definitely feasible for the slightly out of shape, just take breaks. You might be sore the day after 4. Go early to avoid other hikers, I started at 9am. By the time I headed back I passed a bunch of hikers going up. read more

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From Jersey City, this is located about an hour away. Such a huge change in scenery for such a quick drive. What I love most about bear mountain is that not only is it great for hiking but it's a destination. There are other things you are able to do aside from just hiking. They have picnic table and grills for you to bbq. There's a kiddie playground by the lake. The ice skating rink opened up on November 5th so you're able to enjoy that. There's a cute little cabin on site that offers hot beverages and snacks while you enjoy the merry go round. If you're looking for a quick weekend getaway, they have a lodge on site which has a restaurant and a cafe located within. This mini oasis is absolutely fantastic. The trails consist of easy, difficult, and challenging. I was able to do all 3. The easy trail is a light stroll but I highly recommend the difficult and challenging if you're an active person. Take in the beautiful fall foliage and the view not to mention is breath taking! read more

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This is a great hiking spot in CT. Great trails, gorgeous views, and usually very friendly hikers. Come check it out! read more

Bear Mountain - Hiking Near Me

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Bear Mountain is one of the best places to go hiking in Connecticut. It's classic New England...nice and rocky with thick treecover. I have always gone up from the Undermountain Road parking area. It's a nice, safe lot, where I don't worry about leaving my car overnight. Right next to the lot is a large bulletin board with maps and other information. There's also a nearby privvy. The hike up isn't bad. If you take the Undermountain trail all the way up, it's an easy climb to the summit of Bear Mountain. If you take Undermountain to Paradise, you'll hit Bear Mountain going South, and the last few hundred feet will be a nice, steep scramble. I recommend doing that and making a loop out of it. Also, unlike a lot of mountains that are below tree-line, Bear Mountain offers many fantastic views. You can see for miles and miles from the rock mound at the summit. There are also a few stone outcroppings along the way that offer great views. Thanks to our AMC volunteers, Connecticut's portion of the Appalachian trail has some very nice, well-maintained camping areas. I recently stayed at the Brassie Brook Shelter, not far from the summit of Bear Mountain, and it was more than I could ever ask for. The lean-to is in excellent shape, there's a nice composting toilet, two picnic tables, a bear box, a wash pit, and five tent sites. Since the nearby Riga Shelter attracts people due to the view, we had the whole place to ourselves. If you're looking for a spot to go hiking in Connecticut, you should definitely check out Bear Mountain. read more

Excellent hike, the terrain is more like the Catskills or upper Taconics than what you would expect in CT. I have been many times and have hiked more than 75 miles from NY to the MA-VT state line. The section from Lion's Head to Mt. Everett is my favorite. The north ascent can be very dangerous. read more

Fantastic hike! We did the under mountain trail on the sat of Memorial Day weekend. It's definitely a solid incline right from the start, and was tiring but doable. I'm very active but not a seasoned hiker. All age groups on the trail though so it's a good moderate hike for day hikers that takes 3-4 hrs up and back. It was pretty busy & the trail head is well marked and has a privy on site (more of an outhouse). Definitely bring snacks, water, layers, and bug spray. The summit has great views! read more

Bear Mountain - View from the top. - Hiking Near Me

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The best hike that we have in CT. Highly recommended for those in the area. Here is a video that shows what you can expect along the hike as well as the summit of the mountain. https://www.youtube.com/watch?v=4ni0nyeABms&feature=youtu.be&rel=0&vq=hd720 read more

This is an easy-medium level hike. The hardest part is finding somewhere to park! We were able to park in a tiny lot on the side of the road but had we come any later I doubt there would have been an open space. The view is beautiful of course, but I was surprised by how small of a "summit" was. You don't come close to crossing the tree line so the entire hike is pretty much a walk in the woods. I imagine if there were more people on the mountain that day we wouldn't have much room to move around and take pictures on the actual summit. Dog friendly hike. read more

I hiked this as part of a day-long nine mile hike that also included Mt Everett and Race Mountain, starting at Mt Everett and hiking south. As that seems to be the opposite of how most people hike it, and I haven't seen much out there that mentions the north face of Bear Mountain, I feel that it definitely needs to be mentioned. This is a mountain worth hiking, but if you are not an experienced hiker, it's better to stick to either hiking Lion's Head and then the south face of Bear Mountain, or take the Undermountain Road trail to the trail up the south face of Bear Mountain. Hiking the north face of Bear Mountain at times is much closer to rock climbing than actual hiking. As an illustration of how difficult this trail is, there were portions of this trail that required physically lifting/carrying our 65 pound dog, who is very good at climbing and can jump up 3-4-foot vertical faces. Going down that side is difficult enough, but going up requires extreme care and better than average athleticism, particularly with backpacks. If you are planning on doing a day hike on Paradise Trail (a popular day-hike trail that leads to the bottom of the north face of Bear Mountain), and you are looking for an easy, enjoyable hike, you're definitely better off hiking through Sage Ravine. However, if you are looking for a challenging climb and are an experienced hiker, hiking the north side of Bear Mountain is a great choice and well worth the trip. read more

This is really one of the best hikes in Connecticut. We made the mistake of coming down the north face of the mountain on the AT -- STRAIGHT down over huge rocks! Very grueling! Coming up the south face was much easier; the Undermountain trail is pretty easy. Next time, we'll start at Lion's Head and come up that way. read more