53 Beautiful Winter Hikes in Connecticut [By County]

Although winters in Connecticut can be rough, that doesn’t mean hiking has to stop. In fact, winter hiking in Connecticut can be one of the best times to hike. The trails are less crowded, you’re not nearly as hot, and the trail transforms into something entirely different in the winter months, especially if there’s snow.

There are several excellent winter hiking trails in Connecticut to explore this winter, no matter where you are in the state. Every county has a handful of tried-and-true hiking trails that are perfect for any level hiker to get out and explore in the winter.

Let’s explore 56 absolutely beautiful winter hikes in Connecticut, by county, so you can choose one this winter that works for you! And, don’t forget to make sure you’re prepared to dress warmly and properly when planning your trip out.

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.

Beautiful Winter Hikes in Fairfield County, Connecticut

1. Devil’s Den Preserve

Devil’s Den Preserve is an excellent park located in Weston, Connecticut. There are plenty of easy trails around the lake in this park, or more moderate trails to a viewpoint for a longer trek. So, no matter whether you’re only looking for something easy (which I recommend if it’s your first time out hiking in winter), or something a bit more challenging, Devil’s Den has something for you.

The AllTrails link I typically share with people is this one, but don’t be put off by the distance. This one just includes everything you may want to see – so if you’re looking for something shorter (which I recommend in winter), then just think about heading around the lake instead of up to the viewpoint.

And, I’ve highlighted this park on this site before, so if you are looking to read more about this trail before checking it out this winter, you can get my guide here.

2. Mianus River Park

I’m not sure there can be an article on hiking trails in Fairfield County without listing Mianus River Park. Located in both Stamford and Greenwich Connecticut, this park is a must-see for locals or anyone passing through. Interestingly, this park is populate year-around. Even if there’s several inches of snow, you’ll see plenty of people trekking around this park.

But, the popularity in winter is part of the reason I highly recommend this place as a starting point for new winter hikers. You’ll be around others should you need some support (or you slip and fall). Plus, when it snows the beauty of the minus river is hard to beat anywhere else in Fairfield County.

Mianus is another park I’ve highlighted on this site before, so check out my guide if you’re looking to check out this park in winter!

3. Trout Brook Valley

If you’re looking for a more remote trail, and something where there’s unlikely to be anyone else for most of your hike, then Trout Brook Valley is where you want to be. This park is located in Easton, CT and is truly one of those quiet, peaceful hikes you can do at any point of the year – but if its snowed, then I’m pretty sure you could hear a pin drop it’s so quiet.

Because of the serenity of this park, it’s a great winter hike to get out and be by yourself. Plus, the trails are easy-to-moderate, so it’s not too strenuous of a day. However, there is rarely cell service here, so if you are going to be hiking here, and hiking alone, be sure to have the proper safety gear while hiking in winter. You don’t want to get caught in an unfortunate situation without a way to contact someone.

If you’re looking to visit Trout Brook Valley, my guide to this park and the blue-green trail is a great one to get you started hiking here in winter.

4. Westmoreland Sanctuary

So, I do have to confess. Westmoreland Sanctuary isn’t actually in Fairfield County. It’s just over the border in Mt. Kisco, NY but for anyone in this part of Connecticut, it’s a super quick park to reach. For that reason I’m including it in this guide (that and because I do think it’s an excellent park to visit in winter).

Westmoreland Sanctuary has a lot going for it at any time of year. But in winter, it’s stunning, and if you hit it after a snow you’ll likely be the one breaking the trails either with your micro spikes or your snow shoes. After a snow, this park truly transforms into something else and it’s absolutely worth a visit.

The trails here are mostly easy, though a few lean moderate. My guide detailing the park can help you choose which trail you may want to do for your next hike. And, I can assure you no matter which you choose you’ll be happy you visited this park that’s just outside of Fairfield County this winter.

5. Shelton Lakes Recreation Path

The Shelton Lakes Recreation Path is another longer trail (at least according to AllTrails), but don’t let that dissuade you. It’s a relatively flat out-and-back trail, so you can make it as long or as short as you want.

On this path you’ll stroll past some water (which in winter will likely be frozen to some degree), and along boardwalks and wide, flat nature trails to soak in all that winter in Connecticut has to offer. You should note though that the portions next to the water can get icy, so be sure to have some microspikes with you while hiking. You may not nee them, but it’s always better to have them and not need them than need them and not have them.

6. Pequonnock Greenway Trail

The Pequonnock Trail in Trumbull, Connecticut is a bike trail – although I wouldn’t recommend taking your regular bike on this trail. Mostly mountain bikers, and hikers who are looking for a nice flat, wide trail, visit here. In the winter, although it can get icy, it is a great way to get out an enjoy the cool weather and snow (if there’s some present).

This is an out and back trail, and some people say it’s not super well marked, so I’d always recommend having an AllTrails map for this location before visiting, especially in winter. But if you’re looking for a peaceful winter stroll in the woods, then this is a great winter hike to explore.

7. Rail Trail (Ridgefield, CT)

There are so many rail trails across Connecticut, but this one is located in Ridgefield, Connecticut. Like most other rail trails it’s flat, gravel in certain locations, and is pretty remote and enjoyable for a nice quiet stroll/hike in the woods.

Now for this park you’ll need to watch out for parking since there isn’t any at the trailhead. Instead you’ll need to park at the nearby dog park and walk to the end of Halpin Street to access the trail. But once you’re on the trail you shouldn’t have an issue with this beautiful out-and-back easy hike in winter.

Beautiful Winter Hikes in Litchfield County, Connecticut

8. White Memorial Park

Oh, White Memorial Park in Litchfield. This is probably the park to visit in Litchfield no matter the time of year. Seriously, this park has stunning trails in spring, summer, fall, and winter. In winter though I think these trails (like so many others in Connecticut) truly take on a new feel.

The boardwalk trail is one of the more popular ones, and although I personally haven’t done it in winter I can imagine it being extremely beautiful to visit. But there are plenty of other easy trails around the main entrance of the park that are sure to provide those serene and peaceful winter views you’re looking for on your winter hike.

9. Meeker Trail (Macricostas Preserve)

Out of all the trails in this list so far, the Meeker Trail is definitely the most moderate. There is some (small) elevation here and a very beautiful view point should you wish to climb to it (it’s only ~750 ft, but still a bit of a climb).

The elevation part is pretty short though, so it may be worth the trek up especially in winter or after a snowfall. The Meeker Trail is very well maintained and is super popular throughout the year (although less so in winter). I’d highly recommend visiting this trail at least once during a winter in Connecticut, just for the views and the great experience on the trail.

10. Clamshell Loop in Steep Rock Preserve

Steep Rock Preserve is one of my favorite parks in the entire of Connecticut. There are several great trails here including the Bee Brook Loop to the suspension bridges and the visit to the Quartz Mine (where you can see actual quartz). But the best winter hike is absolutely the Clamshell Loop.

The Clamshell Loop takes you to the Steep Rock Preserve rail tunnel that everyone always tries to find. Now, this tunnels is VERY icy in the winter, so you’ll definitely need spikes to hike here (seriously – don’t try going without spikes, you will regret it). But the icicles that hang off the rocks and the tunnel, and the incredibly winter photos you get here absolutely make this trail one you have to put on your winter hiking list.

11. Camp Columbia State Park

Another park full of easy trails that make for great winter hiking, but my recommendation is the Camp Columbia Tower Trail. Now this trail is super short (coming in only around half a mile), but it takes you to a beautiful tower.

This tower is stunning by itself in winter, but you can also climb to the top and get a beautiful winter view of the surrounding area as well. Just be careful not to slip when climbing the stairs in winter! This trail is also not super popular at all so it’s likely you’ll have it all to yourself to enjoy the winter sites.

12. John Ross Trail

Marshes are beautiful at any time of year, but in winter they’re truly something else to view (plus, you don’t have to deal with the bugs in winter and marshes are definitely known for being buggy). The John Ross Trail is a 3-4 mile out and back trail that takes you through a marsh in Goshen, Connecticut.

There isn’t a ton of elevation here – it’s pretty flat. But it’s definitely long enough to get your fill of winter hiking in an easily accessible trail, while taking is the beautiful sites of winter. Highly recommend.

13. Burr Pond

If you like hiking around water, then this is going to be a trail for you. The entire Burr Pond trail walks you around Burr Pond over the course of a 2.5 mile loop.

Now, walking near water in winter is beautiful in winter, but those colder temperatures come with ice on the trails. Don’t attempt this trail unless you have micro spikes as you’ll need them out here. But, with the proper gear to prevent from slipping all over the place, you’re sure to get beautiful views of the frozen pond and if it’s snowed, some beautiful snowy woods.

14. Sue Grossman River Greenway

The Sue Grossman River Greenway is an entirely paved walkway, but I like to include it as a hike because it does go through a wooded area and it’s pretty remote. Plus, in winter you really do feel like you’re out in nature with this scenery and the fact there are few other people around.

It’s also good because the paved trail means that it’s accessible to those who may otherwise have a hard time navigating other hiking trails, or who are recovering from injuries but still want to get out in the woods in winter. The only thing is during winter you always need to be careful of ice. The trail isn’t plowed in winter either so if it snows be prepared with the proper gear to navigate.

For this trail, there’s 5.6 miles of out-and-back flat, paved trail for you to enjoy!

15. Great Mountain Forest

Now, if you’re looking for a trail that’s really really really remote where no one else will be then the Great Mountain Forest is for you. AllTrails doesn’t have any easily accessible trail links for hiking here, so you’ll need to make sure you head to the website and print off (or take a screenshot of) their actual trail map.

But hiking out here in winter is surely to give you a really unique and gorgeous writer hiking experience and something that if you’re a bit more experienced with hiking (and hiking in winter), I would highly recommend.

Beautiful Winter Hikes in New Haven County, Connecticut

16. Racebrook Tract Trail

Racebrook Tract is a tiny little trail tucked away in Orange, Connecticut. It’s not really a popular trail and is one that only locals tend to visit, mainly due to its size and the fact that it doesn’t have any major overlook points or features.

But, when you’re hiking in winter those overlook points aren’t as enticing and many people prefer beautiful woodsy strolls instead of intense climbs. And Racebrook Tract completely fits that bill. Plus, after snow, this trail transforms and you’ll surely enjoy getting into the woods to enjoy the winter weather and nature.

17. Turkey Hill Preserve

A second option to Racebrook is another little trail tucked away in Orange, Connecticut and that is the Turkey Hill Preserve. If you’ll be hiking here you’ll take the 2.0 mile loop around the park on a fairly easy trail. Plus, it doesn’t get its name from nothing – you’ll probably see turkeys there when you go (just keep your distance).

Again, no major overlook points or specific features to highlight here, but it will be a pretty, easy stroll in the woods during winter and one that can absolutely be worth visiting after snowfall.

18. Sleeping Giant

Sleeping Giant is one of the largest and most well-known parks in all of Connecticut. So, even in winter this park is a popular place to be. And, if you’re someone who wants a bit more of a challenging hike during winter then you’ll definitely find more challenging trails here than in any of my other suggestions thus far.

Easy hikes in winter include the tower trail (although it can get icy on the gravel and does have some elevation to it). Another easier/moderate trail is the yellow, red, and white trail loop – covering only 1.8 miles with limited elevation gain.

If you’re looking for something a bit harder then I’d recommend the violet trail, or some combination of trails that covers the violet. It’s a beautiful, less traveled trail in the park with some elevation gain at the beginning.

Now, you may want to try the blue trail in winter and some people do this, but I personally won’t recommend it. The blue trail is dangerous in the best of conditions, and in winter it’s going to be icy and even more dangerous. If you know what you’re doing and have the proper gear then go-for it, but for me I’ll hike the blue trail in warmer, less icy weather only.

19. Castle Craig

Castle Craig is a beautiful hike at any time of year, but I do think it has something extra special to it when hiking in winter. But, know this is a moderate trail and hike – not something super flat or easy, so be prepared for some challenge when choosing to hike here in winter and maybe avoid it after a snowfall if you don’t feel comfortable hiking in snow.

But, if you do want to take on this hike, then I’d recommend the loop that goes to Castle Craig and around Mirror Lake. That way, you’ll get a bit of everything including an icy lake view when you’re out hiking.

20. Bent of the River

Bent of the River Audubon Center has several easy-to-moderate trails to choose from. An easier recommendation is the Cascade Trail that along can be a bit longer (4.0 miles) has only a little elevation and is a great hike in the woods.

This park tends to be pretty empty and in winter that is even more true. You’ll truly get a remote, secluded experience by hiking here in winter. Plus, after a snowfall, this park transforms and you’ll enjoy some breathtaking scenery of Connecticut nature under snow. Something you don’t want to miss.

21. Tyler’s Mill Preserve

Tyler’s Mill Preserve is a little local park with lots to offer its few visitors. If you’ve never been before, I recommend the 7.0 mile trail on AllTrails, but not because you need to do the whole distance, but because it’s a great starting out point to get your boots on the trail and pick a distance that works for you. There are several other small trails intersecting with this one that you can explore.

The trails here are winding, so expect some twists and turns, but they all generally fall on the easier side of moderate. It’s a great place to bring a pup in winter and just get out an enjoy the cold weather!

22. Quinnipiac Linear Trail

If you’re looking for a super flat, straight trail to explore in winter then the Quinnipiac Linear Trail is where you want to be. This is a paved trail, which is great for accessibility, unless it’s icy. You always need to look out for ice in winter, especially after snowfall and snowfall melt, and this trail can get very icy in the right conditions.

But, as long as you’re prepared for the ice, then this is a great little trail to get out an explore without elevation, making it great for those of you with smaller kids. The only downside is that it is right next to the highway, and you can hear road sounds so it’s not the most serene. But it is a nice little stroll in winter to enjoy, and sometimes that’s all you’re looking for.

23. Giuffrida Park

Giuffrida Park is known for its beautiful fall foliage views, but don’t discount this park in winter either. It has quite the sights no matter the time of year, and winter is no exception.

Now, the only thing is what level of hike you want to do. If you’re looking for some rocks and some moderate elevation gain/climbing, then heading up to Chauncey Peak is probably your speed. You’ll need to watch for ice and make sure you have micro spikes with you if you choose to take this trail.

For those looking for something flat, wide, and easy, then taking the loop around Bradley Reservoir is likely more your speed. There will still be ice here (you should always expect ice next to bodies of water in winter), but you won’t be climbing anything. Plus, the view is truly stunning from down here as well.

Beautiful Winter Hikes in Hartford County, Connecticut

24. Northwest Park

If you’re looking to do a bit of snowshoeing this winter, then you’ll likely want to check out Northwest Park. This park is a great place for newer snowshoers to get started, as they offer rentals and some tips for those just starting out.

The trails here are perfect for snowshoeing. They’re generally flat, easy, and fun to explore. Plus, under snowfall you can really expect the beauty to shine.

25. Winding Trails in Farmington

Winding Trails is a great place to visit, but it’s also one of the only recommendations on this list that isn’t free for everyone. You need a membership to visit here (or to be friends with someone who is a member). But, there are great winter activities here, including winter hiking and snowshoeing. They also have rentals available, but again you must be a member.

I do have to state that I’m not a member here, nor have I ever been. With that said, I have seen several recommendations by members that it is a great place to hike/snowshoe in winter, so if you’re nearby and want to partake is some of their other year-round activities, then getting a membership may be just what you’re looking for.

26. West Hartford Reservoir #6

I absolutely love this hike at anytime of year, but it really pops in fall and in winter. This hike is pretty popular, as it heads around the reservoir is a pretty flat 4.0 mile loop that’s the perfect spot in winter to get outside and get some fresh air. Anytime you’re near water though, expect ice even though this hike generally has less icy spots than some other around-the-lake hikes I’ve highlighted here. But it can get pretty muddy, so I’d expect that.

If you’re looking to do something a bit more adventurous, this trail connects to another trail that will take you all the way to Talcott Mountain and Heublein tower. This is fully a moderate hike, especially in winter, and is upwards of 7-8 miles, so only take this trek if you’re prepared to be out for that long.

27. Jones Mountain

Jones Mountain is an interesting hike, because although it can be hiked at anytime of year it’s actually more known for its winter hiking. It’s also an excellent place to snowshoe (if you have your own, or you rented from somewhere like REI).

Although it’s on a mountain, and does have an overlook point to enjoy, it doesn’t require a lot of climbing or elevation, and the hike itself is only 2.5 miles and rated as easy. So, it’s a great place for kids or dogs in winter, even on snowy days.

28. Cheney Rail Trail

The Cheney Rail Trail is definitely more of an urban “hike” than something remote or super deep in the woods. I know that’s not everyone’s cup of tea, so wanted to put that disclaimer first. But, if you are in the Manchester area and are looking for something quick to get some fresh air and get outside in winter, then the Cheney Rail Trail is what you’re looking for.

This flat trail is out-and-back, so you can hike for as long as you want. It’s mostly paved, with some packed dirt/gravel in places, and is accessible (especially in the first mile). It is popular, and it is urban so you’ll almost certainly be on the rail trail with other people while hiking here. But, even with that, it’s a great way to get outside without much planning or traveling in the winter months.

29. McClean Game Refuge

Coming straight off the urban hike above, the hiking at McClean Game Refuge is much more secluded. In winter, it’s not uncommon to be sharing the entire park with one 1-2 other people/groups. So, it’s easy to get on a trail and enjoy it is in solitude.

There are a lot of easy and moderate trails to choose from here, and really none are better than others – it’s more of just where you want to head. Since I like to provide recommendations to help get you started, I’m going to recommend the Blue and Yellow blaze loop. I chose this one primarily because I prefer loop hikes and this would is a good short distance, easy, and accessible to most. Be sure to have spikes though as it will get icy in winter, especially a few days after snowfall.

Beautiful Winter Hikes in Middlesex County, Connecticut

30. Chatfield Hollow

I’m not sure I’ve ever written a Connecticut hiking recommendations post without including Chatfield Hollow State Park. This is an excellent little park with lots to offer, even during winter.

For winter though, this hike has something special to offer that you don’t see in too many other hikes. It has a waterwheel! Now, I know that might not be exciting to everyone, but seeing a waterwheel is cool anytime of year – but in winter, after a snowfall, it’s truly something out of a magazine. It’s worth checking this trail out just for that. Plus, it’s an easy, shorter (3.5 miles) hike – so great for most to get out an enjoy.

31. Devil’s Hopyard

Devil’s Hopyard is another larger park with plenty of trails to choose from in winter. However, this park has the Muddy Brook Waterfall (which is more beautiful than this name suggests). If there’s been a lot of precipitation in winter (snow or rain), then I love seeking out waterfalls in winter. The icicles are something else and usually it’s the only time of the year where you can enjoy the falls completely solo.

In Devil’s Hopyard the Millington Trail Loop will take you to the falls, so this is the trail I’m going to recommend. But if you want something a bit longer, or harder, any of the trails at Devil’s Hopyard can be great winter hikes.

32. Airline State Park Trail

The Airline State Park Trail is a super long trail that extends over 40+ miles and into several cities/towns. But, it starts in East Hampton, Connecticut so I’m highlighting it first in this section.

Now, just because the trail extends for that many miles doesn’t mean you have to hike it the entire way. Just do what you can and treat it as any other out-and-back hike. The Airline trail is great for people who are looking for relatively flat, wide trails, to stroll through the woods in winter. It’s an easy hike, but one that will get icy in winter – so bring those spikes!

33. River Highlands State Park

The trails at River Highlands are all generally short, easy, winding trails that run along the river. If you’re looking to hike here in winter, expect some solitude and beautiful views of the Connecticut river in winter.

Any trail here will be good, so choose the one that works best for you. If you’re looking for a recommendation, then this 1.5 mile trail is a great starting point.

34. Wilcox Woods

If you’re looking for a super off-the-beaten path hike in Connecticut, then Wilcox Woods is for you. I wasn’t even able to find this park/trail on AllTrails at all – so you know it’s not super well-known and you’ll likely get a pretty secluded winter hike here.

With that said, there aren’t a ton of trails – only 3, and really they’re all so short you can easily combine them into one single trail. No big features here, but you’ll get a beautiful stroll in the woods, making it a great winter hike in Connecticut to visit.

35. Machimoodus State Park

Another beautiful park with a few different trail options to choose from. My favorite is this one that meanders through the interior of the park, with some (quite overgrown/washed out) off shoots that extend down to Salmon River. If you can’t tell from my description, I highly recommend not heading down to the river and staying in the interior of the woods for this trail.

But the interior of the woods is gorgeous and is exceptionally beautiful after a snowfall. Highly recommend this trail/park as a prefect winter hike to explore in Connecticut.

Beautiful Winter Hikes in Tolland County, Connecticut

36. Nipmuck State Forest

What a better winter hiking trail than one named the Snow Hill Road Trail! There are of course other trails in Nipmuck State Forest, but given its name this one is the most commonly traveled in winter.

It’s flat, wide, and 4.3 miles one-way (it’s an out-and-back), so you can hike for as little or as long as you want!

37. Belding Wildlife Trail

This trail near Bread and Milk Road in Vernon, Connecticut, is composed of a beautiful evergreen forest – which can be lovely to visit in winter. Although the trail is short, it can be challenging to follow at points, especially once you get past the river.

I’d recommend visiting after a fresh snowfall, and to plan to only meander in a little bit and stay near the river (although it will be icy).

38. Bigelow Hollow State Park

There are so many trails in this park you can go back and back again and try out a new trail each time. Even if you hike the same trails in summer/fall, I do recommend checking them out again in winter. It’s an entirely different experience in winter.

But, if you’re looking for a recommendations I personally love to hike near water in winter. So, you can check out this pretty easy, short trail next to Bigelow Pond. Expect ice though – it’s always icy near this pond in winter.

39. Joshua’s Trust

This little park has a few easier trails to enjoy. One of the downsides of this park is that it’s incredibly buggy in the warmer months. But, if you’re hiking here in winter you do not have to worry about the bugs at all! So, you get all the beauty without any of the bugs!

One popular trail here is the 1.9 mile loop around Knowlton Hill Preserve, which is great to explore in winter.

40. Sharon Land Trust

The trails at Sharon Land Trust are excellent choices if you’re looking for something truly off the beaten path and without a lot of other hikers. As of 2022, there are no AllTrails links for the trails here, so unless you’re truly a local most people won’t be out here hiking.

There are a lot of different preserves within the land trust, but a great one to explore if you’re visiting for the first time is the Dalton Land Trust. A few different trails to choose from here, including one with a summit. Just be sure if you are going to be summitting in winter you have micro spikes and are prepared to cover some icier areas both when going up and when coming back down.

41. Mansfield Hollow State Park

This is a beautiful park, and if you can manage to visit after a snowfall, you’ll be in for a treat. A few different trails to pick from here, but I like this short ~2 mile out-and-back trail that goes through the park to the lake.

This is not a very popular trail, but is a common one for people with dogs to take them out for a bit. The trails are wide, flat, and the scenery is stunning.

Beautiful Winter Hikes in New London County, Connecticut

42. Yiantic Falls

I haven’t highlighted a ton of trails with waterfalls in this post, primarily because waterfalls can get really icy in winter (duh, right?). And although you should expect ice on hiking trails in Connecticut in winter, if it’s too icy, I don’t want to recommend them in case someone without the right equipment heads there and falls

Yiantic Falls is a bit different since it’s only 0.3 miles from the trail start and it’s right in the middle of the city. So, while it won’t me the most remote of hikes, it is a great way to visit a waterfall in winter without going too deep into the woods. You should still expect ice though – you should always expect ice.

43. Babcock Ridge Preserve

This little park is part of the Avalonia Land Conservancy and is beautiful to visit in winter. I’ve recommended a lot of trails near water (they’re personally my favorite), but if you’re looking for something more woodsy and less icy/watery than this trail is for you.

The 1.0 mile trail doesn’t pass by any water at all. So, you’ll get a truly remote, woodsy experience for your winter hike here. Plus, it’s not a super popular trail at all so you’re likely to be one of the only ones out there, even during typically busy hours.

44. Fort Shantok

This hike is beautiful, and comes with a bit of history attached. It’s located on the Mohegan reservation and has a few different monuments along with a cemetery along the trail to explore. And, if you do have younger kids – the park has a playground for them to joy either before or after the hike.

The hike itself is only 0.7 miles and is wide, flat and in the summer wheel chair accessible. In the winter it can be accessible too – but you do need to just watch out for snowfall and ice, as if there’s too much of either you won’t be able to easily traverse on wheels.

You do need to keep your pups at home though as this is a dog-free trail.

45. Niantic Boardwalk

If you like beach strolls/hikes, then this trail will be for you! I know some people don’t feel that boardwalks or ocean walks are hikes – but if you’re from Connecticut then you’ll know that a lot of the ocean-front hikes are like this and are very beloved by locals.

This boardwalk is 2.0 miles out and back, and when you’re on it you’re definitely going to get excellent views of the ocean in winter. You should expect a few people, but in winter the boardwalk is nothing like it is in summer. In summer, it’s packed, but in winter it’s only the few who brave the cold you’ll have to share with view with.

This is another dog-free area, so you will need to leave your pups at home when hiking here in winter.

46. Gillette Castle State Park

Gillette Castle is a Connecticut staple, and it’s truly worth visiting at any time of the year. First, you have the castle, which is stunning in any season (potentially even more so in winter). But beyond the castle, the grounds around the castle are really nice to visit as well, and take on a particular new view in winter.

A great trail to use to explore around the park is this trail, which is rated as easy and is only 2.2 miles. You’ll see the castle, a beautiful stone bridge, and beautiful views of the river.

47. Nipmuck Trail

In eastern Connecticut, the Nipmuck trail is a well-known, well-loved, and well-visited trail. And it’s hard to imagine why, it’s easy, fairly long (out-and-back), and beautiful. Since you can hike as little or as short of the trail as you want, it makes it a great winter hike if you’re just getting started hiking in cold weather.

I love the beautiful bridges and the water views this trail has to offer. But, as I’ve repeated several times in this guide – watch out for ice. Cold weather often makes for icy bridges and trails.

Beautiful Winter Hikes in Windham County, Connecticut

48. Bull Hill Preserve

If you’re looking for an overlook, then this is the winter hike for you! I haven’t mentioned too many overlook trails in this guide because of how icy it can be to climb. But, the benefit of this trail is that there really isn’t any climb and you still get the lookout!

When you park you’re already at the top so there’s no climb. The only downside is that getting to the parking area can be challenging – you need 4-wheel drive and some good tires. This is true at any time of the year but in winter it’s especially true. The dirt road is washed out – so unless you have the right mode of transportation you won’t be able to get to this trail.

49. Diana’s Pool

The Diana’s Pool trail is a short 1.3 mile trail with a beautiful walk alongside a river. After a snowfall, it can get icy, but it’s a beautiful place to get some peace and enjoy some winter air and views.

Because of how easy and flat this trail is, it’s a great place for families, new hikers, kids, and dogs.

50. Allanoch-Wolf Preserve

I feel like I’m being a bit repetitive here – but the trails here are another really peaceful, easy, stroll that is perfect and beautiful in the winter months. This 3.1 mile trail has a few offshoots you can take if you want to lengthen or shorten you trip, but not all of them are well marked so be sure you have a downloaded map (or physical map), so you know where you are and don’t get turned around.

51. Pine Acres Lake

Pine Acres Lake is much more a swamp than it is a lake. So, in summer it’s filled with bugs, and I don’t know about you but buggy trails for me kind of take the fun away from the experience of hiking. Luckily in winter, you don’t have to worry about that at all and instead you get beautiful frozen views of the water.

This trail is easy, but if you’re worried about icy rocks then you’ll want to stay on the left side of the lake only (so don’t do the entire loop). If icy rocks don’t worry you then feel free to take the entire trail around the loop of the entire lake.

52. Airline State Park Trail

I’ve already highlighted the Airline trail once before in this guide, but I’m highlighting it here again because it’s just that long of a trail and it’s totally worth visiting in multiple counties (or in whatever one is nearest to you.

Starting in North Windham, this section of the trail is an 11.8 mile out trail (and another 11.8 miles back), but only hike it for as long as you feel comfortable and turn around (no need to do the entire 22+ mile trail).

This trail is relatively easy, flat, and beautiful to hike in the winter.

53. Mashamoquet Brook State Park

And last, but definitely not least, is one of the trails at Mashamoquet Brook State Park. There aren’t a ton of trails here to choose from, but I like this 4.2 mile moderate loop around the park. Nothing specifically spectacular here to note, but it is a nice winter hike in the Connecticut woods and one I think most people will enjoy.

It is moderate though, and there are plenty of rocks, a bit of elevation, and it will be icy and slippery in the winter. But if you’re properly prepared for the hike, then it shouldn’t be an issue!

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Well, there you have it – 53 beautiful winter hikes in Connecticut! I hope that this guide has helped you find a hike or two near you that you can explore this winter. Winter hiking is truly a unique experience, and Connecticut has some great trails to get out and explore the peace of nature in winter. Happy Hiking!

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