Okay so maybe not so high, but CT is home to some breathtaking (and rugged) hikes. Though somewhat ironically, you wouldn’t quite know it. CT is flanked by the Berkshires Catskills, Green Mountains and White Mountains. We’re not the first state anyone in the country, let along New England, thinks of when it comes to hiking. And yet, we rank as one of the best states in the nation. We have 1,455 hiking trails per 1,000 miles, which is a fancy way of saying we have a tremendous amount of trail systems and open space for such a small state. I don’t know if I agree that we have the “best” hiking, but we have a lot that’s unexpectedly beautiful.
I’m sometimes asked to recommend trails to people new to hiking, or those just looking for something different, or what I think is worth seeing. So I’ve been wanting to put this list together for a while. This will focus on the “must see” hikes that are worth the effort to visit. Part 2 will feature a few hikes that may not be a destination all by themselves, but are worth visiting if you’re in the area. Part 3 will focus more on my love-hate relationship with eastern NY western CT and the incredible hikes they have on that side of the state.
Jessie Gerard Trail
A real hidden gem because of its unassuming location. The Jessie Gerard Trail is part of the People’s State Forest in Barkhamsted, CT. It’s good for a fantastic hike up along a waterfall, gaining about 600′ over a half mile. Whether you’re new to hiking or not, that’s pretty steep. But unlike the grand options our NH and VT friends have, this is only steep for a little while. There’s some minor scrambling (which means you use your hands to pull yourself up) it’s otherwise a straight up thigh burner. You’re rewarded with outstanding views from a couple of large ledge outcroppings. While all these hikes have views, this is one of the few that doesn’t feel like you’re in CT. While you’re in the area, make sure to check out another CT icon- the Saville Dam at the Barkhamsted Reservoir.
Horse Guard State Park
In terms of best bang for your buck, you won’t beat Horse Guard State Park in Avon. The trail is a very short, mostly flat woods hike until a steep, but quick rock scramble to the peak. Once at the top, you’re greeted with spectacular near-360 degree views including Hartford, and in the distance Hueblein Tower and the Hanging Hills in Meriden. The trail can get muddy after a rain, and it’s arguably too short depending on where you’re coming from. I expected, and deserved, a bit more punishment before getting this view as a reward. But I say this is worth seeking out.
Heublein Tower/Talcott Mountain
Speaking of the Heublein Tower! A classic CT hike that is on most lists, and with good reason. The hike up Talcott Mountain to Heublein Tower is a must-do. The trail is a little less than 3 miles round trip, and a good workout. The yellow trail starts steep on a wide dirt access road. This is the hardest part of the hike and definitely gets your heart pumping, but is also easy terrain, so no ankle twisters. Once you reach the top of the road, the incline peters out greatly and the rest of the hike to the tower has numerous views along the way. The tower is open Friday – Sunday, there’s also an outdoor pavilion to eat at, water to refill and bathrooms. A really good all around hike and great for families. They also host some very fun events throughout the year, like Hike the Mic and Tower Toot. One caveat, once you get to the top, the trail runs along a ridge of rocky outcrops. Great for views, of course, but there are some very steep drop offs to be aware of.
Sleeping Giant
I’m not aware of any official records, but Sleeping Giant in Hamden is routinely praised as being the most popular hiking destination in all of CT. There’s tons of trail options ranging from easy to hard, grand views or forest walks. I like Sleeping Giant for the extended rock scramble on the blue trail, which is what I think makes it a unique hike in CT. It’s about 600 feet of elevation gain just over a half mile. If you’re looking for an adventure, this is the trail for you. It’s definitely hard, and is actually considered one of the hardest hikes in CT, and is also a very cool experience. The scramble is alongside an old quarry, so while it is steep, it has spectacular views all the way up. This feels more like hiking in the White Mountains than CT. Don’t be too intimidated by it though, people of all ages have done this hike. You can hop onto a trail at the top to connect to the 4 story stone tower with 360° views. If tickle-belly inducing hikes aren’t your thing though, there’s plenty of easier ways to get to the tower than following what the above map calls “scary climb”.
West Peak
West Peak has a couple of notable superlatives- it is the highest traprock peak in CT (lol), and also the highest point within 25 miles of the ocean over the whole east coast (ooooh!). I’m drawn to this area because it can be seen from all over the state and has a very identifiable steep western prominence. It’s often overlooked in favor of Castle Craig, found on East Peak, but you can hit both with this hike. I actually recommend it. I park across the highway of Interstate 691 and take the steep trail going up the face. Although on a recent trip with a friend, I accidentally missed the turn and took the “easy” way up. The open traprock views at the top are some of the best in the state, with clear vistas of Sleeping Giant. This was one of the other times I didn’t feel like I was hiking in CT. You can also drive to the top, so if you want to catch this view without the hike, I still think it’s worth it. There’s ledge outcrops all between Castle Craig and West Peak, and I’ve seen many people put up hammocks and just enjoy the day. And because it’s in central CT, it’s pretty much accessible for anyone in the state.
Rand’s View
Rand’s View. The undisputed best view in the state- at least according to anyone who knows about it. We just talked about how great West Peak is because of its centralized location. That is not the case here. Rand’s View is located in Salisbury, CT in the northwest section of the state. It’s about 2 hours from me. The Litchfield Hills are pretty hard to get to from anywhere in CT because there’s no major interstate that travels to there. That means places like this, for better or worse, aren’t well known. But I was so desperate to check this out once I learned about it, that I actually made the trip twice. In fact, even my second visit was so memorable that I forgot that on the way there, my timing belt broke and completely trashed the engine of my car. And yet Katie and I still made the trip after getting a tow back home.
Something that makes it different from the others on this list is it’s not a view from a summit. The sweeping green pastures with mountains in the background is pure heaven. It’s also part of the Appalachian Trail and in fact, a lot of thru-hikers say it’s one of the best views on the whole AT. But, just because it’s not on a mountain doesn’t mean there isn’t a climb. You either climb up (and down) Raccoon Hill, or Mount Prospect which are meh on their own. It also means you have to climb them again on your way out. But the best bang for your buck is parking at the end of Sugar Hill Rd and hiking an old spur trail to the AT shelter. From there is a fairly technical and steep hike/scramble up a waterfall, but it’s by far the shortest and easiest way to get to Rand’s View. Katie hates heights, and this was one that had her nearly bail. But she pushed through and said she was glad she did! And I really want to reiterate- this is a 2 hour drive for me and I’ve been twice and can’t wait to go again. If you only visit one of these hikes, this needs to be it.
Mt. Frissell/CT Highpoint
Am I emotionally ready to talk about this one yet? Probably not, but here goes. I described this as one of the most miserable hikes I’ve done. But in hindsight, there are some redeemable aspects to it and I would recommend it. First, it features the CT highpoint, and that’s rare because we’re one of the few states where our highest point isn’t on our highest mountain. While the summit is in MA, there is a sliver of the mountains’ butt that hangs in CT. It’s naturally fitting for that to be our true high point.
And while the summit has no view, you do have to climb over Round Mountain to get there, and that view is one of the best in the state. It is also the SECOND highest mountain in the state. Very wide open at the top, and a lot of wild blueberries for you foragers and fruit-eaters out there. I am neither.
Just a little further past the CT highpoint is the CT/NY/MA tri state border monument, and the added bragging rights of saying you hiked in 3 states in one day. And if you still have some gas in the tank, you can tag Brace Mountain about a mile away. Although I haven’t done that particular hike yet, it looks to have stunning views.
Downsides are it’s over 2 hours away, and you don’t even get there from CT. Most of the drive is in MA. Parking can be scarce and it’s down a long bumpy dirt road. The hike itself goes up Round Mountain, down it, up Mt. Frissell, down to the CT point and border, back up to the summit, back down, back up to Round summit, and finally down. I combined this with Bear Mountain just because I wasn’t going to make a separate 2 hour trip, but that certainly didn’t help my exhaustion level. I also remember that once I signed the register at the highpoint, there was a storm rolling in so I had to huff it back to the car. Okay, I realize I may not be selling this very well so let me end with this. There are very good views along the way, and there are bragging rights, and being the CT highpoint makes it a must-do. In spite of my grouchiness, I am definitely going to be doing this again.
Bear Mountain
The highest mountain in CT, Bear Mountain is accessed from the Mt. Riga State Park. It is also part of the AT. So a couple of little bragging rights. There’s two main trails to the top, I did the scramble which was a great workout. There’s an AMC hut you can reserve to stay in, and an AT tent site nearby, as well as the Sage’s Ravine back country campsite. This could be a cool option if you wanted to bag multiple hikes over a couple of days. Like Mt. Frissell and Rand’s View. And a host of other hikes in western CT that are amazing. Is this soapbox time?
Yes, it is soapbox time. I have a complicated relationship with my feelings towards western CT. I’ll be the first to admit that the best hiking in all of CT is in western CT. But, like I said above, it’s so hard to get to. It leaves the realm of “I’m going for a hike” and turns into “I’m going on a trip”. It’s a destination. And there are far better options if you have to make that kind of time commitment. I think this area would make a phenomenal long weekend trip, and I’ll make another post of my favorite western CT hikes another time. But for me, these last 3 aren’t casual options for a hike. But they ARE worth making the effort to seeing at least once. Back to the post!
The summit of Bear Mountain has good views as a reward. You easily see into New York and several lakes to the east. You also have to climb stone ruins to get to the view, which was interesting. I’ll also note that the parking for Bear Mountain is the same for Mt. Frissell, so if you did have to make a special trip out this way, it may be worth trying to do both hikes.
As I finish writing this post, I realized that you can see many of these areas from others listed. For instance, you can see Bear Mountain from Round Mountain and Rand’s View. Horse Guard State Park, you can see both Heublein Tower and West Peak. Maybe a fun hiking bucket list I need to do is to hike across CT from the high vantage points.
Stay tuned for Part 2! Have you hiked any of these? What are your favorite CT hikes and views?
