12 Winter Hikes in Connecticut; Scenic Winter Trails!

There’s nothing like walking through a silent winter forest and if you’re looking for Connecticut winter hikes that feel like a magical wonderland then you’ve come to the right place!

It’s time to start getting excited about winter hiking and these 12 winter hikes in Connecticut are perfect for inspiring your next winter trail adventure.

You’ll notice a lot of these hikes are in the northwest corner of Connecticut. 🗺

This is the area with the highest elevations in CT so if you’re looking for snow this area is your best chance of finding it!

Of course if there’s been a recent snow storm then any hike in CT will turn into a winter wonderland and the ones on this list will be made even better!

Each trail includes the AllTrails link (in title), basic facts, special features, and GPS coordinates or a link to directions. 🚗🔗

Before we get into the top CT winter hikes let’s get into a few tips for winter hiking:

• Check Trail Conditions: my favorite way to do this is to check the most recent reviews of the trail on AllTrails. Just click the title of each hike and you’ll be taken to AllTrails scroll down to see the reviews!
• Dress in Layers: There are so many factors that can affect the “real feel” out there. Check out my post – what to wear winter hiking to get a quick rundown!
• Bring Traction Devices: I bring my microspikes on every winter hike! And if there’s deep snow out there then you’ll want to wear snowshoes!

So let’s get to it:

❄️12 Best Winter Hikes in Connecticut!❄️

1. Pine Knob Loop, Cornwall

• Miles: 2.5 mile loop
• Elevation Gain: 770 feet elevation gain  
• Level: Moderate
• Parking: Click here to navigate to 41.833338, -73.383675, large parking lot on Route 7
• Special features: Hatch Brook Falls and two different lookouts facing east

The Pine Knob Loop trail in Connecticut stands out as one of the most beautiful trails to explore year-round. This scenic loop leads you past a series of waterfalls for you to admire as you begin the ascent (taking the loop clockwise).

You’ll be treated to two incredible lookouts over the Housatonic River Valley. Facing east, the second one is a great spot for sunrise! You’ll also be you’ll be walking along the famous Appalachian Trail in CT for about a mile on this hike.

Experience Pine Knob Loop, lookouts, and waterfalls in the beauty of winter!

2. Bear Mountain, Mount Riga State Park

• Miles: ranges – different trails to choose from, click here for different routes up Bear Mountain
• Elevation Gain: range
• Level: Moderate
• Parking: Click here to navigate to 42.02876, -73.42887, large parking lot for Appalachian Trail
• Special features: Tallest mountain in CT

Bear Mountain, Connecticut’s tallest peak, is an exciting adventure for hikers in any season, and there’s something magical about tackling it in winter!

I love the thrill of the unknown as you make your way there—wondering if you’ll find yourself in a winter wonderland at the summit, even when there’s no snow anywhere else.

Since it’s the highest point in Connecticut, Bear Mountain often surprises with pockets of snow and cooler temperatures, so be sure to layer up and be prepared with your winter hiking gear.

There are several ways up Bear so check out my post to pick your trail! ➡️ Best Routes up Bear Mountain in CT ✨

3. Steep Rock Preserve, Washington Depot

• Miles: 3.8 mile loop
• Elevation Gain: 393 feet elevation gain  
• Level: Moderate
• Parking: Click here to navigate to 41.62158, -73.32513, large lot
• Special features: Views, tunnel, Shepaug River

Steep Rock Preserve transforms into an absolute wonderland with a blanket of fresh snow! Walking along the Shepaug River under the tunnel of snowy trees is magical.

A few favorite spots along the trail include the lookout with its gorgeous views, the unique tunnel, and crossing the hanging bridges. If you’re lucky enough to visit after a recent snowfall, Steep Rock Preserve is like stepping into a storybook scene—you won’t want to miss it!

4. Jessie Gerard Trail in Peoples State Forest, Barkhamsted

• Miles: 2.9 mile loop (options to choose a longer hike here)
• Elevation Gain: 700 feet elevation gain  
• Level: Moderate
• Parking: Click here to navigate to 41.94268, -73.00726, medium sized parking area along East River Rd
• Special features: Sweeping views facing west, two different lookouts

Peoples State Forest is a top Connecticut hike any time of year, but in winter, it transforms into what feels like your private oasis! With far less visitors compared to the busy summer and fall months, it’s like your private snow dusted forest where you can soak in the wild beauty here.

From the top of Jessie Gerard, the views are breathtaking in the winter looking across at the snowy mounds of American Legion Forest and the Farmington River cutting between them.

Be sure to pack your microspikes for potentially icy spots on the initial climb which is a little steep and rocky!

5. Round Mountain, Taconic

• Miles: 2 miles out & back (trail linked above shows 8+ miles but it’s only 1 mile to the top of Round Mtn then you can turn around!)
• Elevation Gain: 700 feet elevation gain  
• Level: Moderate
• Parking: Click here to navigate to 42.02884, -73.42878, parking spots along Rt 41 Under Mountain Rd (can be messy in winter!)
• Special features: Beautifuk views facing east 🌅

One December morning, I was lucky to catch a vibrant sunrise at the top of Round Mountain, surrounded by frosted trees—it was truly what we all wish for when we hike in the winter!

Have you not heard of this one? Many people haven’t. This hike sits on the edge of Connecticut, right where CT, MA, and NY meet, and for such a quick climb, the views are spectacular.

Again, bring your microspikes for the somewhat steep but short climb in the beginning. (We gotta put in some effort for those views! 😍🌅)

6. Mount Tom Tower, Litchfield

• Miles: 1.3 miles out & back
• Elevation Gain: 337 feet elevation gain  
• Level: Moderate
• Parking: Click here to navigate to 41.69532, -73.27997, large parking lot
• Special features: Almost 360-degree views atop Mount Tom Tower

Come spy on the town of Litchfield under a blanket of snow from atop Mount Tom Tower!

The walk up to the tower isn’t long and then you’ll just have to climb a few sets of its stairs to experience these beautiful winter views. This is a go-to hike for sunrise or sunset if you want to make this view even better with a magical golden hour glow. ✨

7. Kent Falls & Kent Land Trust

• Miles: 1 mile out & back
• Elevation Gain: 250 feet elevation gain  
• Level: Easy (stairs and paved pathways leading to falls)
• Parking: Click here to navigate to 41.7768, -73.41674, large lot along Rt 7 Kent Cornwall Rd, out of state fee on weekends
• Special features:Tallest waterfall in Connecticut!

Come check out what Connecticut’s tallest waterfall looks like in winter!

I love frozen waterfalls and visiting Kent Falls when the crowds of the summer have faded away is like a quiet little dream. Some parts of the falls might be frozen while others are flowing, so it makes for a very interesting visit as you never know what it will look like til you’re there!

And since this isn’t a huge hike I suggest going to nearby Kent Land Trust after for an easy and short walk along the Housatonic River or head minutes down the road to the first hike on this list- Pin Knob Loop.

8. Pond Mountain and Fuller Pond Loop, Kent

• Miles: 3 mile loop
• Elevation Gain: 613 feet elevation gain  
• Level: Moderate
• Parking: Click here to navigate to 41.75988, -73.48265, large lot along Fuller Mountain Rd
• Special features: Loop around pond plus views

Come walk around (or maybe even on!) the frozen Fuller Pond in Kent this winter. Not only does this winter hike have a scenic loop around the pond but it’ll also take you up to Pond Mountain with some views here.

It’s very peaceful here and whenever I’ve been I’ve only seen one or two other groups. Come experience the peace and winter beauty at this gem of a CT hike!

9. Hatchett Hill, Tariffville

• Miles: 
• Elevation Gain:
• Level: Moderate
• Parking: 
• Special features: 

Snow or not, the views of the Farmington River snaking its way through the forest below make this hike incredibly scenic even in the winter.

What I love most is the walk there you’ll be up on a ridge and since all the leaves will be gone you’ll be able to see through the trees into the forest around and below you with little peaks of views as you approach the big lookout.

10. Hedgehog Trail to West Mountain, Simsbury

• Miles: choose either the 2 mile route or 4.8 mile route both routes up Hedgehog detailed here
• Elevation Gain: 640 – 912 feet elevation gain (depends which route you choose from above)
• Level: Moderate
• Parking: Click here to navigate to 41.87901, -72.86604, small lot just off Westledge Rd
• Special features: Cathles Falls, multiple stellar lookouts!!

This hike is a winner in any season and is incredibly scenic so even if there’s no snow on the ground – you won’t get bored!

Hedgehog has a waterfall (Cathles Falls), multiple lookouts, streams, bridge crossings, and more. The variety of things to see on this hike always makes it a fun outing and keeps me coming back in any season.

The views face east so this has also been a go-to spot for me for sunrise!

11. Stone Man Mountain via Iron Trail, Norfolk

• Miles: 2.7 miles out & back
• Elevation Gain: 672 feet elevation gain  
• Level: Moderate
• Parking: Click here to navigate to 41.97214, -73.27239, lot along Canaan Mountain Rd.
• Special features: 270-degree views

Check out CT’s lesser known trails this winter! With beautiful views of the surrounding valley for not that long of a hike up – Stone Man is a great choice for winter in Connecticut.

12. Cobble Mountain Loop, Kent

• Miles: 3.4 mile loop
• Elevation Gain: 856 feet elevation gain  
• Level: Moderate
• Parking: Click here to navigate to 41.76098, -73.49403, large parking lot within Macedonia Brook State Park
• Special features: Beautiful mountain views

You’ll definitely work for this hike at Macedonia Brook State Forest. But the views are BIG so it is worth it!

Hiking to the view super scenic too. You’ll be in the 2,300 acre Macedonia Brook State Forest and with the leaves off the trees you’ll be able to see through the trees at the vast expanse of forest.

That’s it friends!

I hope this helped inspire your next CT winter hike. Every winter hike is a true adventure and as long as you are dressed properly (check out my 🌟 women’s winter gear budget guide ❄️) you are sure to enjoy it!