12 Winter Hikes in Connecticut; Scenic Winter Trails!

group of woman and dogs winter hiking in connecticut — CT winter hike #5 on our list!

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. (And if you're still in need of winter hiking gear check out my post ➡️ Winter Hiking Clothes For Women ☃️❄️)

You'll notice a lot of these hikes are in the northwest corner of Connecticut. 🗺 That's because this is the area with the highest elevations in CT so if you're looking for snow this is your best chance at 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. 🚗🔗

woman smiling in blue fleece and pink snow hat with snowy mountains in the distance at pine knob loop in cornwall connecticut

hiking up to bear mountain in winter in connecticut

❄️Before we get into the top CT winter hikes here are a few winter hiking tips:

Check Trail Conditions: my favorite way to do this is to check the most recent reviews of the trail on AllTrails.
Dress in Layers: Base layer, mid layer, and an outer layer/shell. There are lots of factors that affect the "real feel". Check out my post - what to wear winter hiking if you need the basics!
Always pack microspikes: I bring mine on every winter hike. Walk on icy trails with ease and they're so lightweight, just clip them to your bag in case you need them!
Snowshoes for deep snow after a fresh snow storm

Table of Contents

❄️12 Best Winter Hikes in Connecticut!❄️

1. Pine Knob Loop, Cornwall

winter hiking view from pine knob loop in cornwall ct

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

group of hikers on top of bear mountain in connecticut

man winter hiking with snowshoes at cobble mountain in connecticut

Miles: few different trails to choose from, check out my post ➡️ 3 different trails up Bear Mountain in CT 🌟
Level: Moderate - difficult
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.

3. Steep Rock Preserve, Washington Depot

woman and two dogs hiking at steep rock preserve in washington depot ct

steep rock tunnel in winter in connecticut with snow on ground

snowy walk along shepaug river in washington depot ct

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

back of woman on mountaintop in connecticut looking out over rolling leafless hills and golden orange sunset sky above.

man in red fleece with bare mountains behind him.

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 icy spots on the initial climb which is steep and rocky!

5. Round Mountain, Taconic

sunrise at top of round mountain in connecticut with pink and orange skies and snow on ground

sunrise at top of round mountain in connecticut with pastel pink skies and snow on ground

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 or keep going!)
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: Beautiful 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

winter view from mount tom tower in litchfield ct

winter sunrise from top of mount tom tower in litchfield connecticut

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! One of the best hikes to do in Litchfield.

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

woman in blue jacket and pink snow hat with black dog at kent falls in winter

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!

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 until you're there!

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- Pine Knob Loop.

8. Pond Mountain and Fuller Pond Loop, Kent

woman smiling with two dogs on winter hike at pond mountain in ct

2 black dogs and woman standing on frozen pond on fuller pond in connecticut

black dog on frozen pond on fuller pond in connecticut

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: 2.9-miles
Elevation Gain: 410 feet
Level: Moderate
Special features: view over Farmington River

Snow or not, the views of the Farmington River snaking its way through the forest below make this hike up Hatchet Hill in Tariffville incredibly scenic.

What I love most is the walk to the view - you'll be up on a ridge and since all the leaves are gone you can 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

woman posing for sunrise hike in simsbury

light shining on small waterfall. — Cathles Falls (optional!)

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 with it's wide open views from two different ridges (if you do the whole 4.8-mile loop) 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

winter view with snowy trees and mountains in the distance at macedonia brook state park

woman in winter hiking gear with two black dogs on snowy winter hike in kent connecticut

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 clothing guide ❄️) you are sure to enjoy it!