on forest floor with trees with yellow leaves. Connecticut fall foliage

51 Best Connecticut Trails for Fall Foliage [By County]

Connecticut, like most New England States, has beautiful fall foliage. Now, you can always drive to see the trees (and Connecticut has some gorgeous fall road trip destinations), but I think there’s something special about hiking to view the fall colors. But it’s not always easy to figure out where to go to get the best views. So, if you’re like me, and wondering where to hike in Connecticut to see the fall colors, then you’ve come to the right place.  

Below I’ve listed 51 of my favorite Connecticut hiking trails perfect for viewing fall foliage. In this list, there’s something for everyone – including easy, flat trails, trails around water, and trails with climbs to higher viewpoints. No matter your hiking level there’s a trail in this list for you. I’ve also included AllTrails links to every trail in this list, so it’s easier for you to get to the views! 

I hope that by visiting these trails you’ll discover the true beauty that Connecticut has to offer. I love this state’s hiking opportunities and want everyone to be able to explore our great trails! So, check out our list of hiking trails by county and get out there to experience fall!

Disclosure: This post contains affiliate links and I may receive commission for purchases made through links in these post. All links are to products I highly recommend and have verified.

Fall Foliage Hiking Trails in Fairfield County, Connecticut

Fairfield County isn’t really well known for it’s hiking trails, or for its fall foliage views. But, there are plenty of opportunities to see fall foliage in Fairfield County and some trails that I think are particularly special to check out. 

Let’s explore them more below. 

1. Collins P. Huntington State Park – White, Red, and Blue Loop

Huntington State Park is Redding, Connecticut is probably my favorite park in all of Fairfield County. This place is gorgeous at any time of year, and during the warmer months you can even kayak here (which I love doing too). 

As for the fall foliage, it’s breathtaking. There isn’t really elevation or a big overlook spot, but the trail that loops around Huntington  Pond is beautiful and filled with deep colors during the fall. The White, Red, and Blue loop trail from AllTrails is a great 2.6 mile, easy loop that would be great for any-level hiker, including kids.  

2. Pooatuck State Forest to Squantz Pond – Pine Hill Trail

Sqantz Pond is another Fairfield County favorite with excellent fall foliage views. Now, you can start at Squantz Pond itself (I’ll highlight that below), but if you’re looking for a bit of an overlook then you’ll actually want to start in the nearby Pooatuck State Forest. 

The trail connecting the two locations is the Pine Hill Trail, which is a 4.6 mile, moderate trail with rocky terrain. This is a true moderate trail, and for some may be a moderate-hard trail. It’s also not well marked in certain places, but with a map you’ll be treated with some spectacular views of Fairfield County fall foliage. 

3. Squantz Pond State Park – Squantz Pond Trail

Again, Squantz Pond is a beautiful place to see fall foliage, but not everyone is up for the elevation and rockiness of the trail above. So, if you’re looking to see the foliage around here but want something a bit easier, then this trail is for you. 

The Squantz Pond Trail is a 2.2 mile easy trail that walks alongside Squantz Pond for half the trip, and in the woods of the  Squantz Pond State Park for the other half, so you get a bit of everything on this trail. This is a great walk in the woods and is also great for families who want to get some views. 

4. Trout Brook Valley – Any Trail

Trout Brook Valley in Weston Connecticut offers a really remote hiking experience for Fairfield County and one where you can really soak in the colors as you walk on the trails. Now, this isn’t a park where you’re going to be in awe over a beautiful overlook, but this is more of an experience where you’re walking in the woods with fall foliage surrounding you. 

Because there isn’t one single view point you can really take any trail from their Bradley Rd. entrance. The 3.0 mile blue/green loop is an easy/moderate trail I’ve taken several times and recommend. But if you want something flatter and easier, the pink trail located a little farther south is a great way to go. 

5. Mianus River Park – Mianus Maze Trail

Mianus River Park in Stamford/Greenwich Connecticut is a Fairfield County staple. I’d be willing to bet that there isn’t a single person from those two cities who hasn’t meandered here at least once. 

There are several trail options here, but the main staple is the Mianus Maze Trail, which is yellow-blazed on the trail map. This is a 5 mile trail that encircles the outside of the park, but can easily be made shorter by using any of the cross-through trails in the middle of the park. There aren’t any overlooks in this trail, but you do get to walk next to the Mianus River and take in all the bright yellow trees that come out in fall. 

view of small river surrounded by trees with fall foliage. Yellow leaves, red leaves, and green leaves. View of kayaking to see fall foliage in connecticut

Fall Foliage Hiking Trails in Litchfield County, Connecticut

The northwest hills of Litchfield County is where you’ll likely get the best colors and fall foliage views in the entire state. There’s no shortage of trails here to explore that will have you blown away with beauty during the fall. It was so hard for me to narrow down this list, as there are so many other places beyond what I’ve listed here, but these are the ones that I, and several other members of the local hiking community, think are the best ones. 

Let’s explore these 8 recommended fall foliage hiking trails Litchfield County, Connecticut below. 

6. Lover’s Leap State Park – Lover’s Leap Trail

Another classic Connecticut hike, Lover’s Leap State Park is favorite local spot year around. But in the fall, the colors pop and are absolutely stunning. 

The Lover’s Leap Trail takes you over the lock bridge and up to the overlook point in an easy 1.2 mile trail. Seriously, for the view this offers you’ll be shocked at how easy this trail is – perfect for families or those who just don’t want a strenuous hike to an overlook point.  

7. Kent Falls State Park – Red and Yellow Loop Trail

Kent Falls has one of the most spectacular waterfalls in the state and is a favorite local hiking spot. The hiking here isn’t strenuous at all, and is mostly made of stone stairs that go up the length of the water fall, and meandering dirt paths just next to the falls. 

At any point during the year Kent Falls is beautiful, but during fall the colors add a whole extra dimension to the experience. The  red and yellow loop is an easy trail that takes you up (via stone steps) and around the falls to fully explore, but you really can take any trail here for the views. 

8. Peoples State Forest – Jessie Gerard Trail

There are a limited number of Connecticut hikes that lead to spectacular miles-long views of the surrounding area. Peoples State Forest offers one of these in the Jessie Gerard Trail. 

This trail is a 2.9 mile moderate hike that leads you up to an overlook point where you see rolling hills for miles. The up-hill part of this trail isn’t even so bad because it’s mostly stone steps (though there is small rocky climb right before the summit). If you’re looking for more of a challenge, or a longer hike, you can do the entire 7.0 mile Peoples State Forest Loop which covers the same overlook point. 

In fall, these rolling hills are covered in beautiful colors and you’ll want to just sit and soak them in for hours from this spectacular view point. 

overlook at Peoples State Forest

9. Saville Dam – Tunxis Trail

All the Connecticut classic hikes appear to be in Litchfield, because the Saville Dam is another picturesque Connecticut landscape. Even if you’ve only ever seen one picture of Connecticut in your life, my guess is that it was of the Saville Dam (and it was  probably taken during fall). 

Now, the Saville Dam itself only has concrete walking and biking trails to drive around the dam and the reservoir. These views are stunning, especially in the fall, and so although it’s not exactly hiking, it’s 100% worth the trip. 

But, if you do want to combine it with hiking, just a few minutes up the road is a portion of the Tunxis Trail. This is a moderate trail, and is out and back – so you can hike for as long as you want before turning around and heading back to your car. There is an overlook of Pine Mountain about 2.5 miles into the hike, which may be a good landmark for anyone looking to hike this trail in fall. 

10. Housatonic Meadows State Park – Pine Knob Loop

Are you looking for fall foliage views with big rolling hills that extend into the distance? If so, then you’re going to want to head up to the Pine Knob Loop

This 2.5 mile moderate hike, is on the harder side of moderate, with some rock scrambles. This also covers a part of the Connecticut Appalachian Trail, so you know that means it’s going to be an up and down hike. But, it’s going to have some incredible fall views that will be worth the effort to get them. 

11. Mount Riga State Park – Bear Mountain Trail

Since we just explored an overlook on the Appalachian Trail, let’s explore another one. Bear Mountain isn’t only in NY – there’s a Connecticut version that has some excellent views you’ll definitely enjoy in fall. 

The Bear Mountain Trail is a moderate trail with some elevation (you are going up a mountain). This trail lis just over 6 miles because it goes to the top and then loops around. But you can just do an out-and-back to the top for a 5 mile trail (but with half of it going straight down hill). 

One point to note is that the viewpoint at the top is only accessible by climbing a large stack of rocks on the summit. So, only a certain number of people can take in the views at one time (probably around 10-15). 

12. Hidden Valley Preserve – Yellow Circle / Overlook Trail

Hidden Valley Preserve is one of my favorite parks in the entire state. There’s just so much to do here, and it’s so inconspicuous because a lot of people haven’t ever heard of this park. Throughout the year you can enjoy the suspension bridges, the quartz mine, and an overlook. 

For fall color viewing, this entire park is sure to be gorgeous. If you’re looking to visit the overlook, the best trail is the quartz mine trail that offshoots to the overlook (on the official trail map it’s the yellow circle trail). This is an easy/moderate 2.8 mile trail, but you can shorten it if you don’t want to go all the way around the mine. 

I also recommend heading up to the suspension bridges as well to get some really unique views of fall in Connecticut. The yellow circle trail will take you that way, but there isn’t an AllTrails map (that I’ve found) that covers both – so you’ll need to be a bit innovative and create your own. 

13. Steep Rock Preserve – Yellow Circle Trail

Steep Rock Preserve is just south of Hidden Valley Preserve (they’re both run by the Steep Rock Association) and it too has a yellow circle trail that is great for fall foliage views. 

The Yellow Circle Blazes Loop  is a 3.7 mile moderate trail that spends about a mile walking alongside a river before climbing to an overlook. Elevation isn’t too bad (only about 450 ft), but the climb does prevent horses from making it to the top (while they’re allowed at the flat river portion). 

All parts of this trail are beautiful, but the overlook here is more expansive (in my opinion) than the one at Hidden Valley Preserve. So, if you are looking for something different (and even less crowded than Hidden Valley), then this view is for you. 

View of the Thoreau suspension bridge at hidden valley preserve

Fall Foliage Hiking Trails in New Haven County, Connecticut

More central areas of the state have just as many hiking trails perfect for viewing fall foliage as other areas. New Haven County is no exception – from Sleeping Giant State Park, to walks around Lake Wintergreen and the Scoville Dam, there’s plenty to see and enjoy during fall in New Haven County, Connecticut. 

Let’s dive into 8 of my recommended New Haven County hiking trails perfect for viewing fall foliage. 

14. Hubbard Park – Castle Craig Trails

In New Haven, Hubbard Park is going to be the first go-to place for those fall foliage views. The blue blazed trail here has several incredible viewpoints, the most well-known of which is Castle Craig, which is a stone tower known for it’s beautiful views. 

Now, the blue trail itself is accessible by many side trails. For shorter hikes (but still moderate), I’d recommend the Mirror Lake, White Trail and Castle Craig loop. This 3.3 mile loop takes you near water and up to the castle for fall views at both levels. 

If you’re looking for something longer and more challenging, the Metacomet, East Peak, Castle Craig loop will take you to all the blue trail viewpoints giving you plenty of places to soak in the fall foliage. 

15. Nature Conservancy – Higby Mountain

Off of Route 66 is an out-and back trail for Higby Mountain, one of the states lesser known spots for viewing fall foliage. The view from the top of is mountain provides some incredible views of Meriden and the surrounding hills and is totally worth the trek. 

If you do plan to take this trail you should know that it is marked as moderate BUT it does contain some rock scrambles. Some people think it’s not so bad – but if you’re a newer hiker you may want to attempt this one with others or try something a little easier on the list for your first go. The view is worth the attempt, though,  as long as you feel comfortable with rock scrambles while hiking. 

16. West Rock Ridge State Park – Lake Wintergreen

West Rock Ridge State Park is a New Haven County favorite for both hiking and kayaking. This park has something for everyone – which is why I’m highlighting two completely different trails in this fall foliage list. 

The first is the Lake Wintergreen trail. This trail is a flat, easy, 1.5 mile trail that loops around Lake Wintergreen. There isn’t an overlook as part of this trail, but the fall colors spread around the lake are bright enough that you don’t want an overlook. Plus, this trail is accessible for any level-hiker including small children who’s feet may tire out easily. 

17. West Rock Ridge State Park – Regicides Trail

For those at West Rock Ridge State Park who are looking for a trail with a little more elevation, distance, and an overlook, then the Regicides Trail is where you’ll want to be. You’ll still start at Lake Wintergreen, but eventually hike up to get a view of it and other nearby lakes (plus those views). 

The Regicides trail is a 7.0 mile trail that walks you alongside the west rock cliff to get some beautiful views of Hamden and the surrounding areas. I did a complete write up of this trail, and honestly its one my favorites in the entire county (at anytime of the year). But, you are guaranteed to get some beautiful views on what is typically a fairly empty trail. 

views at regicides trail in west rock ridge state park

18. Sleeping Giant State Park – Yellow or White Trails

Sleeping Giant is the best known park in New Haven County, and potentially even the entire state of Connecticut. And, this park has definitely earned its reputation as there’s so much to do and see. 

For fall foliage viewers, there are plenty of different trails where you can get a peek at those colors. For those wanting the standard sleeping giant experience, the tower trail will give you some views, but expect it to be exceptionally crowded. 

That is why if you’re looking for an easy/moderate hike that isn’t too long and has less people on it I recommend the Yellow or White trails. The White and Yellow Loop trail on AllTrails covers both in a 2.3 mile moderate trail and you’ll definitely see some beautiful overlooks. 

If you want more of a challenge you can combine the hard blue trail with the yellow/white trails – but don’t attempt this unless you’re more experienced. People have died doing the Blue Trail at Sleeping Giant, and no view, no matter how beautiful, is worth that. 

19. Southward Falls Park Trail

Southward Falls Park offers the best of hiking – beautiful fall foliage views AND a waterfall. Plus, the hike on the red trail is only 1.7 miles with very little elevation gain. So, an easy trail with a lot to see. 

Now, since this park doesn’t have a lot of elevation, you shouldn’t expect a single overlook point. But, there is a small fire tower that you can climb if you wish for a small, but higher-up view point. Mostly though, this trail gives you in-the-woods fall views to submerge you into the colors. 

20. Scoville Dam – Scoville Reservoir Loop

The hike around Scoville reservoir and dam is more of a walk than a hike – but because of that its more accessible. This is a longer easy trail (around 3.5 miles), but if you have a stroller or wheelchair it is still accessible for you with all-terrain type tires. 

Essentially the Scoville Reservoir Loop takes you around the the entire reservoir. It can be wet at times, but that’s par for the course when hiking near the water. The views around the water here are stunning and absolutely worth the trip, especially since it’s such an easy walk. 

on forest floor with trees with yellow fall foliage in Connecticut

Fall Foliage Hiking Trails in Hartford County, Connecticut

Some of my all time favorite secret (or at least less crowded) hikes for viewing Fall Foliage are in Hartford County. Of course there are bigger, more popular trails as well, but some of the smaller ones are really great to see some beautiful foliage without being too crowded.

Let’s look at 8 of my recommendations for hiking trails in Hartford County perfect for viewing fall foliage.  

21. Hog Back Reservoir – Walking Trail

The first trail on my list of Hartford County Trails, isn’t really a hiking trail. But, stick with me, because it has some incredibly beautiful and remote views of fall foliage around the West Branch Farmington River. It also has some great kayaking opportunities if you’re looking to get fall foliage views while kayaking

The walks here are pretty much on concrete roads, so anyone can use them. And they aren’t very well known so you likely won’t have to share the space with very many people at all. In fact, there isn’t even an AllTrails spot for this – so you’ll need to park here, and walk up Durst Road in order to see the views. 

But the views are absolutely worth it, even if it is only a short walk to view them. 

22. Windsor Locks Canal State Park – Canal Trail

Another easy walk/hike, the Windsor Locks Canal Trail is a long out and back with fall foliage views along the water. It’s over 8 miles to do the entire trail (total out and back), but you don’t need to do the entire thing. Just walk for as long as you’d like and turn around. 

This trail is an easy trail, but it’s not completely paved, and there are some spots with some bumpy roads or uneven parts of the trail. So if you plan to bring a stroller or need wheelchair access, make sure you have off-road tires on them. Otherwise, it’s a great trail without much elevation, but with incredible fall views. 

23. Horseguard State Park – White Trail

Horseguard State Park is an unsuspecting park tucked away in Avon, CT that has some spectacular views. There’s essentially one trail, a 1.2 mile moderate trail that is generally pretty easy but does have moderate rock scrambles up to the last view point. My full guide describes the full trail, so if you’re not sure if the scramble is for you, I recommend checking it out. 

My favorite part about this viewpoint is that it’s not a popular trail, and there are several different areas at the summit to soak in the views. So, even if someone else is up there with you, you’ll be sure to find a spot you can take in the views completely solo. 

lookout of fall tree colors at Horse guard state park Avon

24. McClean Game Refuge – North Blue Trail Loop

The McClean Game Refuge is a great park near Granby, CT that has a lot to offer in terms of scenery. The North Blue Trail Loop takes you through 3.3 miles of fairly flat terrain, by ponds, rivers, and into the forest. 

There isn’t an overlook here – but the scenery here is gorgeous any time of year, and the fall colors really pop, especially around the pond. In the weekends you should expect it to be fairly crowded, but if you happen to make it out here on a weekday, you’ll likely have the trail to yourself. 

25. Ragged Mountain – Blue and Red Loop

Ragged Mountain is a bit of a more challenging hike (using Connecticut standards). But, since it’s a mountain, you can expect some excellent views especially during fall. 

There are several trails in this park, but the Blue and Red Blazed Loop is one of the more popular moderate trails for its views. It is a nearly 6.0 mile hike with ~900ft of elevation gain – so not too hard, but also can be challenging depending on your fitness level.  But it’s worth it for the views of the Wassel Reservoir, and cliff faces you’ll pass by during the hike. 

26. Pinnacle Rock (Rattlesnake Mountain)

Another moderate trail for a climb up a mountain is Pinnacle Rock, otherwise known as Rattlesnake Mountain.  Due to the climb needed for the mountains, it is rated as moderate (~900 ft of elevation gain in total). There are a few different viewpoints this elevation is split between, but you should expect some climbs. In total, the Pinnacle Rock via the Metacomet Trail is around 4.5 miles out-and -back. 

But, once you’re at the top of these views are truly stunning, especially in fall. This is also an excellent place for a sunrise hike (if you’re into that type of thing) and doing one of these hikes in fall is sure to be even better. 

27. Talcott Mountain State Park

Talcott Mountain probably has one of the best views in the state, especially for fall. Not only does the area around the tower have beautiful fall views but if you climb to the top of the tower you’ll get even farther views of the Connecticut countryside and those fall foliage colors. 

The main Talcott Mountain Yellow Trail is a shorter, 2.5 mile moderate trail that is pretty much guarateed to be filled with people (this is a very popular park). If you’re looking for something less crowded then you’ll need to add on the miles and use the trail extending from Reservoir 6 off of Route 44 and hike the 8 miles up to Talcott Mountain. This is an excellent hike and one that I’ve profiled in more detail if you’re interested in hiking it. 

28. Enders Falls – Enders Brook Falls Trails

What is better than fall foliage views? Fall foliage views next to a waterfall! If that sounds like something you want to see then Enders Falls should be your park of choice. 

The Enders Brook Falls Trail is a quick 1.0 mile out and back trail with very little elevation gain. It’s fully an easy trail leading you to a spectacular shot of a waterfall and some beautiful foresty fall foliage views on your way there and back. 

view from heublin tower entrance at Talcott Mountain state park

Fall Foliage Hiking Trails in Middlesex County, Connecticut

Although its location is a little unsuspecting, Middlesex county has plenty to offer fall foliage seekers! Seriously, there are some beautiful foresty fall foliage views to be had here. 

If you haven’t hiked any of these 7 trails, then check them out this fall! 

29. Chatfield Hollow – Indian Caves and Red Blazes Loop

Chatfield Hollow has a ton of smaller trails to explore. This isn’t going to be a park with an overlook for viewing the fall colors, but you’ll be able to take in the leaves by hiking through the forest or around ponds. When I’ve hiked here there have been lots of bright yellow trees to enjoy. 

Since there are so many trails it’s hard to recommend just one. I like the Indian Caves and Red Blazes loop. It’s a 3.2 mile trail that also takes you buy some great rock structures. But, there is the Schreeder and Old Mill Pond trail (2.7 miles, easy) that you may prefer if you’d like to be near water for your views. 

30. Devil’s Hopyard – Vista, Devil’s Oven, and Orange Trail Loop

Devil’s Hopyard is a well known Middlesex County Trail primarily because of its beautiful viewpoint. The Vista, Devil’s Oven, and Orange Trail Loop takes hikers to this view point and back in a 2.2 mile loop.  

It’s an excellent moderate trail with only slight elevation to get a beautiful view of the Connecticut fall foliage. The only thing is it can be difficult to stay on trail, so make sure you have a downloaded map with you (or paper copy) to help you stay on track. 

31. Hurd State Park – Hurd Park Loop

If you’re looking for an easier hike with some small rolling hills, but for it to have an overlook point for views then this hike is for you. 

The Hurd Park Short Loop is a 6.1 mile easy hike (not flat though – it has small hills). I don’t typically mark trails of this length as easy – but this one truly is as long as you don’t mind the distance. You can shorten it if you want, but some of the other trails at this park are more moderate so you may run into those. 

However, the Hurd State Park Loop will take you to a beautiful overlook point of the CT River and surrounding trees, as well as take you on a good long walk in the forest for the views. This is a great trail to stop at to get some of the lesser-known areas with spectacular views of Connecticut fall foliage. 

32. Machimoodus State Park

Machimoodus State Park is a hidden gem of a park in Middlesex County. It’s a great park to stop by after work for a quick, short, easy hike with beautiful foliage. 

The Machimoodus State Park Trail is 2.0 miles long, rated as easy (it’s mostly flat – though it has a couple of hills) and gives you a small peek-through overlook as well as water views of fall leaves. It’s beautiful, and remote – there won’t be a lot of other people here, so its a great place to soak up the beauty by yourself. 

33. River Highlands State Park – White Blazed Loop

Middlesex County is known for its shorter hikes with beautiful foresty views, and the white blazed loop at River Highlands State Park absolutely fits that bill. 

This hike is a 2.2 mile loop that is relatively flat and definitely marked as easy. On this trail you’ll get views of the Connecticut River, which is beautiful during fall. No major overlook here though, but the views along the river and in the woods are worth the trip. 

34. New England Trail – Section 11

The New England trail extends through the entire state of Connecticut. Hiking the entire trail can be quite the challenge, but most people decide to hike small secitions of it to get out, explore the trail, and see the sights. 

Section 11 in Middlesex County is a great place to hike the NET during fall. This section is 5.3 miles (so 10.6 miles total, out and back), but you can do as little or as much as you’d like. Total elevation for these 5.3 miles is high for CT standards (around 1100 ft), but it’s worth it for the views. There is an overlook point where you’ll be able to get those views you’re looking for. 

35. Meshomasic State Forest

Many Middlesex hikes don’t have great overlooks – but the Great Hill Mountain Loop at Meshomasic State Forest does. By it’s name, you should be able to tell that the overlook is at the top of Great Hill. 

This 3.8 mile trail is moderate, but probably on the easier side of moderate. It has great views, but you should expect some asphalt walking towards the end of the hike, and this section isn’t the most beautiful. But, leading up to the end is pretty and the overlook has good fall foliage views to check out. 

flat and wide hiking trail covered with yellow trees on the way back from hiking kaaterskill falls

Fall Foliage Hiking Trails in Tolland County, Connecticut

Tolland County starts getting into the more rural areas in Connecticut, which means that the fall foliage views start becoming less known. The trails here are ones that you can expect to enjoy by yourself (or at least not to be super crowded). 

So, let’s look into the 4 fall foliage hiking trails in Tolland County, Connecticut. 

36. Shenipset State Forest – Soapstone Tower

This hike is great for the entire family, as it’s actually paved the entire way. It’s an easy 2.3 miles trail, but not an entirely flat one as you are going up a steady incline to the view point. But, it is one of the best easy trails on this list with an overlook, and I think that makes it pretty special. 

The overlook is at Soapstone Mountain, and you will get a spectacular view of the fall foliage of the area. Truly, even if you aren’t into easy hikes or you aren’t from this area – you should check out this view. It’s worth the trip out and may be one of the best in the entire county. 

37. Bigelow Hollow – Bigelow Pond Loop

Bigelow Hollow has so many trails to choose from of varying lengths. The one I want to highlight is the Bigelow Pond Loop, a 1.6 mile easy loop that takes you around Bigelow Pond. 

But if you’re looking for longer trails or more exposure to fall foliage you can easily extend this by going out to  Breakneck Pond or by taking other trails in the park. However, I like this little easy trail because of it’s beauty. Something about Bigelow Pond is stunning in the fall, and is great for its fall foliage views. 

38.Shafran Conservation Area – Orange and Yellow Trail

The Shafran Conservation Area in Tolland County is great for a little local hike. The Orange and Yellow Trails are only 1.5 miles, and it’s a pretty flat trail. This hike is great for a quick jaunt after work/school to get out some energy and see the fall foliage. 

The views here are all foresty views that you get while hiking through the conservation area. But, they’re beautiful and worth the little trip out here. 

39. Joshua’s Trust – Knowlton Hill

Another smaller hike, the Knowlton Hill Preserve hike is a 1.9 mile easy hike through the woods of Joshua’s Trust. There isn’t one stand-out point here, but it’s a great place to experience fall while being in the woods. 

Generally you should expect some bright colors on the trees adjacent to the trail, and to enjoy a quick jaunt out into nature to enjoy the fall foliage. 

Fall Foliage Hiking Trails in New London County, Connecticut

New London County fall foliage hiking trails have a bit of variety. If you’re looking for fall views with castles – it has it. If you’re looking for fall views on a mountain, it has that too. Plus, all the pretty views that come on the smaller, woodsy trails as well. 

Let’s look at 6 New London hiking trails for fall foliage. 

40. Gillette Castle State Park

Gillette Castle State Park is known for the castle itself, but there are several hiking trails around the castle that are worth exploring too, especially during fall.

The trail I’m recommending is the Gillette Castle State Park Loop that is 2.2 miles, and easy. If you want to do more/less it’s very easy to do so by just changing your route. Honestly, the trails here are a little hard to follow anyways, so either have a map or it’s likely the route will depend on which way you think you’re supposed to go. 

But, this trail takes you by the castle, and the water, so you can get those fall views from a variety of viewpoints. 

41. Day Pond State Park – Salmon River Trail

The Salmon River Loop in Day Pond State Park is a bit of a longer hike. Coming in at 6.7 miles, this hike takes you through the park, and by salmon river for some incredibly woodsy fall foliage views. There isn’t an elevated overlook here – but the views near the river are stunning. 

This hike is a moderate hike, with nearly 1000 ft of elevation spread throughout the 6 miles. But it’s not one single climb that gets you – instead it’s the up and down of hills throughout the hike that make it moderate. 

42. Pachaug State Forest – Mount Misery Trail

There are a few Mount Misery’s in the area, and if you search for one the New York one will likely be the one you find. But tucked away in the eastern part of Connecticut is a Mount Misery that is a part of Pachaug State Forest. 

The Mount Misery trail itself is short, coming in at about 2.5 miles. There is a climb, but it isn’t bad and this trail would be rated moderate, but on the easy side of moderate. Once you get to the top, though, the views are stunning and ones that are definitely worth the trip and hike up. 

43. Indian Hill Park – Lantern Hill Trail

The top of Lantern Hill provides hikers a spectacular view of the fall foliage in the eastern part of the state, but you’ll need to work for it. The Lantern Hill Trail is short (2.5 miles) but has a short bout of steeper elevation and some scramblers/bouldering to get to the top.

But once you’ve made it you’ll be glad you made the climb. The views up here are excellent, especially during fall. 

44. Yantic Falls – Indian Leap

The shortest hike in this entire list is the one to see Yantic Falls (also called Indian Leap Falls). In total it’s 0.3 miles, with pretty much no elevation gain, but at the end of it you get to see one of the most powerful waterfalls in the entire state. 

During the fall season, the trees around the waterfall are beautiful. Now, this probably isn’t the hike you want if you’re looking for something remote (the falls are close to the middle of the city), but it is great to visit for a quick hike/walk and some easy fall views.  

45. Babcock Ridge Preserve

Another short, unsuspecting trail is a little 1.0 mile loop in Babcock Ridge Preserve. This is a little local park, and so it’s pretty much empty at most times of the week. But, a portion of this trail becomes spectacular during fall. 

The trail is pretty flat, so it’s an easy 1.0 mile walk, but the colors here are pretty much always stunning and you’ll be glad you visited this little trail in fall. 

Fall Foliage Hiking Trails in Windham County, Connecticut

Last (but definitely not least) are the fall foliage hiking trails in Windham County.  Don’t let being last on the list fool you – these trails have beautiful views that you don’t want to miss. 

Let’s look at these 6 hiking trails in Windham County, Connecticut. 

46. Bull Hill Preserve

If you’re looking for an overlook view without a lot of hiking effort to get there, then the hike at Bull Hill Preserve in Woodstock, CT is what you’re looking for. 

The Bull Hill Preserve trail is 1.7 miles, out-and-back, with almost no elevation. It’s pretty flat the entire way with a great fall foliage overlook view along the trail. The only downside to this trail is that the road up to the parking area is rough. So, if you have a car that can handle some dirt/grass/washed out roads then you can push through. If not, you’ll need to park much farther away and hike in – which will lengthen the hike and increase the elevation. 

47. Air Line Trail

It’s probably a crime against Connecticut hikers to wait until Windham County to discuss the Air Line Trail. This trail is around 45-50 miles along and extends through several counties – and it’s generally a great place to view fall foliage. It’s mostly a paved, flat trail with some great trees with bright colors to enjoy. 

But, if you’re looking for a single point of recommendation, then I like this section starting in North Windham. Like the other parts of the trail, it’s wide, flat, and paved, making it excellent for families, bike riding, or just a nice stroll through some beautiful fall scenery. 

48. Nipmuck Trail

The Nipmuck trail is another long trail in Connecticut extending through Windham County. This one is a bit shorter, coming in only at ~30 miles, but it’s another great trail to explore to see some great foresty fall views. 

The section I’d like to recommend, is the one starting at the very top of the trail. You can hike as far as you’d like on this trail (its an out-and-back), but the trail starts at Breakneck Pond, which is a really enjoyable and beautiful walk in the fall. 

49. Allanach-Wolf Woodlands

Allanach-Wolf Woodlands is a great local park with beautiful fall views. The Allanach-Wolf Woodlands Trail is a 3.1 mile out-and-back, easy trail with little elevation. The main views here are around Lake Marie. 

Because of its location and the fact it’s a local park its generally not crowded at all. You’ll most likely be able to have a nice quite hike where you can enjoy fall and the fall foliage without sharing it with other people. 

50. Mashamoquet Brook State Park

Another smaller, remote park is Mashamoquet Brook State Park.  This loop is a bit longer and more challenging than many of the other local hikes, coming in at 4.2 miles with ~850 ft of elevation. 

Like many of the other local parks, this park too doesn’t have a major overlook point – but you can get those fall foliage views by walking in the woods. The trees and leaves here are beautiful and is a great place to soak up fall. 

51. Diana’s Pool

Last, but definitely not least, is Diana’s Pool. This hike travels next to a particularly pristine section of the Natchaug River that is spectacular in the fall. The Diana’s Pool trail is a 1.3 mile out and back trail with little to no elevation, but plenty of beautiful views. 

Not only is there the fall views, and the river views, but there’s also a waterfall to enjoy as well. What more could you want?

Well, that’s quite the list! We explored 51 recommended hiking trails great for viewing Connecticut fall foliage. There’s likely a few on this list you haven’t been to yet, and so for this fall, and many others in the future, check them out!  Connecticut has a lot of great places for hiking in fall and you should explore them all!

If you’re looking for complete guides to some of the local places to hike check out our Connecticut hiking trails page to find everything you need to know about specific local hiking trails.  

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