5 HIKES IN WESTERN CONNECTICUT

How Much Time Do You Need in CONNECTICUT

Doing all four of the hikes listed on this page will only take a few hours. It’s perfect for a half day in Western Connecticut. Make sure to use the Get Directions feature on All Trails to navigate between the trails, rather than relying on Google Maps. We find that using Google Maps to find trailheads often puts us in the wrong location. Happy hiking!

HIKES IN WESTERN CONNECTICUT

Camp Columbia Tower Trail
Distance: .6 miles
Difficulty: Easy
Time: 15 minutes
This is a super easy, flat hike to a neat tower. The trail can get a little muddy in the winter, so make sure to pack shoes that you don’t mind getting a little dirty. We saw a ton of dogs here, so don’t leave your pups at home for this one! The best part is that the tower is climbable. The narrow staircase wraps around the outside of the tower before bringing you inside to admire the view.  You’ll also notice ruins of a building. You can step inside and check out the graffiti, but there isn’t really too much to see here. The tower is located in a wide open field. There seem to be other trails leading to the tower, but we didn’t have time to check them out. If you do, let us know what you think! 

Fun fact: this area used to house Columbia University students looking to escape the summer heat in the city.


Apple Hill Observation Deck Trail

Distance: 1 mile
Difficulty: Easy
Time: 20 minutes

The walk to the observation deck is a gentle, uphill ten-minute walk. You’ll know you’re at the top when you reach a big, open field. The view from the top of the deck isn’t too different from the view from the bottom, but it’s still fun to climb on up – and it only takes a few seconds. In the warmer months, this is a great field to enjoy a picnic overlooking Bantam Lake. Keep a look out for the entrance to the parking area, it can be a little hard to see. You’ll see a sign on the right hand side of the road indicating the pulloff.

The small parking lot that holds a few cars – maybe five at most. We had the trail to ourselves the entire time.

Pictures from left to right: view from the top of Apple Hill, Mount Tom Tower, inside of Camp Columbia Tower

Mount Tom Tower Trail
Distance: 1.3 miles
Difficulty: Easy – Moderate
Time: 45 minutes

You know when you want a slight challenge, but not too much of a challenge? This is the perfect Connecticut hike for you. It’s a slight booty-kicker, with a rewarding view at the top. It was definitely our favorite hike in the area. Once you reach the tower, you’ll climb up three short staircases to reach the top. Low Clearance! Don’t forget to duck your head as you climb up the last few steps of the ladder to the top of the tower! Try to time it so you can watch the sunset from the top of the tower. You’ll have a scenic view of Mount Tom Pond and a picturesque New England town.
The website states that there is an entrance fee for out of state vehicles.
$15 for weekends and holidays
$10 for weekdays


Hidden Valley Preserve 
Memorial Bridge and Thoreau Bridge Loop

Distance: 1.5 miles
Difficulty: Easy
Time: 30 minutes
Looking for a nice, flat trail with a swinging bridge and a winding river? This is the trail for you! Start off by crossing the Henry David Thorough Swinging Bridge. At the foot of the bridge you’ll see a plaque with a quote by the bridge’s namesake “I went to the woods because I wished to live deliberately, to front only the essential facts of life, and see if I could not learn what it had to teach, and not, when I came to die, discover that I had not lived.” Once you cross the bridge, you’ll meander up the trail while following along the Shepaug River. Before you know it, you’ll descend a staircase and reach the Memorial Bridge. Cross over the bridge to complete your loop back to the parking lot.

There are two parking lots with tons of space in each – one is designated as the parking lot for the Bee Brook Loop and the other is designated as the parking lot for the Bridge Loop, but you can park at either one. If you’re looking for a slightly longer hike with similar waterfront views, check out the Bee Brook Loop (below). 

Hidden Valley Preserve 
Bee Brook Loop

Distance: 2.1 miles
Difficulty: Easy
Time: 45 minutes
This trail follows the same route from the Henry David Thoreau bridge, but then continues straight instead of crossing over the second bridge and looping back to the parking lot.

We visited in winter. With limited hours of sunlight, we didn’t get to hike all of the trails on our list, but next time we want to hike the Quartz Mine Trail.


NOT DONE TRAVELING?

Check out our guides of nearby areas:
Things to do near New Haven
Ultimate Guide to New York City
Perfect Fall Day in New Jersey