Best Fall Hikes in Connecticut

By thewanderingpro | Nov 17, 2020
North America > United States > Connecticut

I am sure Connecticut is not the first place most people think of when it comes to hiking and viewing fall foliage, but in this tiny state you can actually get all of that. Connecticut hikes are of course nothing like climbing Mt. Washington or trekking the Colorado Rockies. The state does offer more manageable and reasonable hikes though, and the views are still worth it. I have put together a list of some of the best hiking spots in Connecticut to view the fall colors, so take a look through and get out on those hiking trails.

Talcott Mountain and Heublein Tower

This hike is probably one of the most popular fall hikes in the entire state and for good reason. The hike is a reasonable distance to get right to awesome views of the Farmington River Valley. Its about a two mile there and back with the first half mile being all up hill climbing about 300 feet in that short distance. But after that initial climb the hike pretty much levels out and you get right to all the overlooks on the ridge. The reward at the end is the Heublein Tower which brings you high above the trees with 360 degree views of the surrounding area. The tower also hosts various events throughout the year, especially in the late summer/fall time with the Hike to the Mic music festival and Tower Toot, their version of an Oktoberfest. Hit this at the right time and the valley will be full of yellows, reds and oranges. This spot is very popular, especially in the fall, so parking is sometimes hard to find or you will be parking far away. If wanting to avoid some of the crowds, you can take a much longer hike and park at Reservoir 6 and go up the back side of the mountain.

Giuffrida Park, Chauncey Peak and Lamentation Mountain

I consider this area the hidden gem of the hikes on this list. The entire park is called Giuffrida Park but you can choose whether to do the Chauncey Peak route or the Lamentation Mountain route (or do both if feeling ambitious). Chauncey Peak is the more popular option due to it being the shortest and most convenient trail, but similar to Talcott Mountain it has a decent beginning incline of about 300 feet in a half mile including a couple rock scrambles. The entire route is about two miles and the views are great especially looking right out over the reservoir. But in my opinion, I find the Lamentation Mountain route much more satisfying and the reason I say this hike is a hidden gem. I can not tell you how many times I have done this hike and I always have the entire ridge to myself. I can spend so much undisturbed time there just taking in the scene of the lake below and hanging hills in the distance. I am lucky if I pass ten people on the entire hike (granted I usually go hiking in mornings to avoid crowds). This might be attributed to the fact that the hike is about four miles long. I find this trek completely worth it though. I also find this trail a bit easier then the Chauncey Peak trail with the ascents being a bit more manageable. The best part is when you finally reach the mountain ridge, you walk along about a half mile of it with views the entire time not just a couple overlooks like the Chauncey Peak trail has.

Higby Mountain

Higby Mountain is probably one of the more "decent" hikes on this list. This there and back hike has two starting points. Both trail starts a bit off the beaten path and easy to miss if you do not exactly know what you are looking for, but both take about five miles round trip. The entrance off Higby Road in Tynan Memorial Park is probably the easiest to get to with an actual parking area, the other entrance looks like your pulling into an abandoned driveway off of Country Club Road. I find this hike very quiet but probably due to the obscurity of getting on to the trail and the length. The hike in general is nice, casually ascending most of the way until you are almost to the top. Just before the top, like Chauncey Peak, there are a couple rock scrambles before getting to the viewpoints. The views are not my favorite on this list since you overlook the highway but still decent views of the hanging hills as well as a decent workout. I have also heard that there is remnants of a crashed plane somewhere on the mountain but have not seen anything myself.

Black Rock State Park

This is a new hike that I just discovered but was pretty cool to find. It is just outside of Waterbury but felt far removed from being anywhere near a city. There is even a little beach at the bottom of the hike as well. Once again, similar to Chauncey's Peak and Talcott Mountain it had a decent beginning incline as well. I would say the view from the overlook is pretty great but unlike the rest of the hikes on this list it really only had one small viewpoint which was unfortunate. This is also probably one of the shortest hikes on this list as well at being only about a mile and half long. You can make it longer though by trekking out to the Old Leatherman Cave which adds an additional two miles to the hike.

People's State Forest

This hike really shows off how the Northwestern part of Connecticut is almost a different world then the rest of Connecticut. But I just want to clarify this hike because it can be a little funky. Although getting to the main entrance of People's State Forest is easy, this is technically not the area you want to be in. Its also on the most southern part of the park and puts you far away from the parts you want to see. If you drive beyond the main parking lot you will see a lot of dirt spots off the road to park in, just look for the lot across from the Jessie Gerard Trail. I suggest taking the Falls Cut Off Trail to get to the top ("easier" to get up then down in my opinion). Its also a fun little hike up due to parts of it being rock scrambles and sometimes after rain you will be hiking up a waterfall. Once at the top take a left on the Jessie Gerard Trail and before you know it, amazing views of the rolling hills of Northwestern Connecticut will appear. A little farther down the trail is another viewpoint overlooking the quaint, tiny town of Riverton with its white church steeple popping out giving a quintessential New England picture. When you have had enough of the views you can turn around and just go back the way you came or take a nice stroll through the other trails in the park. I would suggest not taking the Falls Cut Off Trail back down though, right near this trail there is a second trail back down that is setup as switchbacks to make the descent more gradual and easier.

Ragged Mountain

Like Lamentation Mountain is a frequent hike of mine, so is Ragged Mountain. This hike I find though is a bit busier then Lamentation, even if getting there early (not as busy as Talcott in the fall at least). This place is also a rock climbers haven, so very frequently you will see them climbing the ragged mountain face. This is also a decently long hike as well at about four miles (pending what route you decide to do). I usually do the orange/blue or white trail to start then follow the Metacomet Trail to the blue/red trail to get back to the entrance. But you can make this longer or shorter if you want. One thing that sucks about this park is the lack of parking, getting there early usually helps but you could end up parking far down West Lane if not timed right. The hike is definitely worth it though and I find it a more gradually ascending hike to the mountain overlooks then some of the others on this list. The path is definitely more rolling with constant ups and downs making the trek a bit more interesting then just a straight path. The beauty of this hike is there are viewpoints on all sides of the mountain allowing different views from each stop. There is also a lot of room on the a couple of the overlooks along the Metacoment portion where I have even seen people spreading out and enjoying picnics. Maybe one day they'll put a proper car park in.

Rattlesnake Cliff or Pinnacle Rock

Rattlesnake Cliff and Pinnacle Rock are both also funky parking hikes like Ragged Mountain and Higby Mountain. There is a small dirt lot right off Route 6 to reach Rattlesnake Cliff or just park on the side of the road on Metacomet Road (pretty much in front of someones house) to reach Pinnacle Rock. I put these two together because they are technically on the same trail and not far from each other but combining them into one hike might be a little unconventional. Both are peaks on opposite sides of a valley. So once you climb up one you will have to hike all the way back down and back up again to reach the other peak. They do not really offer a good round trip hike either so once you reach one peak or the other you have to turn right back around and go the way you just came. It is possible to do both, as I have done it before, but I would recommend just doing one or the other though. That being said Pinnacle Rock is the quicker of the two hikes, timing from where you park to the top. Similar to Chauncey Peak, Peoples State Forest and Higby Mountain, this hike also involves some rock scrambles to get to the top but the view is awesome especially at sunsets. Rattlesnake Cliff is a bit longer at 2.5 miles round trip, the hike being a gradual ascent to the cliff viewpoint. Although the viewpoints are not huge they are definitely expansive enough to fit a lot of people (definitely much bigger then Black Rock).

Castle Craig

Castle Craig is the only spot on this list that technically you do not have to hike up to but can drive all the way to the top (but whats the fun in that?). Like Talcott Mountain has Heublein Tower at the top, Castle Craig also has a tower as well that mimics something from an old English stone castle (if the name was not a clue enough). I recommend parking somewhere down in Hubbard Park though to start the hike. There are several trails that you can take to the top of the mountain but just be prepared once you start heading up that the slope is decently steep (so just remember this for the trek back down). Since there are several trails in the park, to actually get to Castle Craig make sure your route includes the blue Metacomet trail and you are on the East Peak. Once at the top you can see for miles, although the view is a bit more residential then the other hikes on this list.

Steep Rock Preserve

Steep Rock Preserve is a unique hike on this list. You are definitely in the middle of nowhere when out on this hike. This hike can vary in distance depending on the time of year you go. You can always park at the top of Tunnel Road and hike from there and do the complete four mile yellow loop hike. Or if not attempting this in the winter, you should be able to drive down Tunnel Road and park next to the foot bridge over the river. If parking here, hiking up to the summit is much quicker and gets you faster to the beautiful views of the rolling hills of Western Connecticut. The trail then would just be a there and back or you can complete the entire yellow loop (or mix it up with some of the other trails which consistently crossover each other). Besides the cool foot bridge over the river, the remnants of an old railroad bed is still in the park, including a tunnel where the train went through the hill which you are able to walk through (if you dare enter a black hole). This tunnel is why I am calling this one of the more unique hikes on this list.

Here are a few other locations to check out for getting those fall views while hiking in Connecticut. Unfortunately I have not made it to these locations yet but they are on the list.

Bear Mountain - Bear Mountain is the highest peak in Connecticut so guaranteed to get some of the best views in the state from here.

Sleeping Giant - Another hiking spot that is probably just as popular as Talcott Mountain in the fall so prepare for the crowds you will encounter. It also has a Tower at the top like Castle Craig and Talcott Mountain.

Lantern Hill - This hike overlooks the Pequot Reservation and Eastern Connecticut's green valley. Reward yourself with some ice cream at Buttonwoods after and thank me later.

This is my list of hikes you should take this fall to embrace the colorful land that mother nature will grace us with. What are some of your favorite places to hike in Connecticut to view our Fall foilage?

-The Wandering Professional

Hiking Higby Mountain Nature Castle Craig Black Rock State Park Steep Rock Preserve Fall Peoples State Forests Ragged Mountain Lamentation Mountain Giuffrida Park Chauncey Peak Rattlesnake Mountain

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Written by thewanderingpro
Hi, my name is Matt and I run a travel, foodie and drink guide under the name 'The Wandering Professional'. I try to deliver authentic guides aimed for the everyday 9-5 style adventurer. Follow along on my adventures and read my tips and suggestions for the many places I travel. Feel free to reach out as well, I would love to connect with the community!

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