5 Great Hiking Trails in Connecticut for Fall Foliage

While the White Mountains of northern New England are the usual destination for fall foliage hiking, avid leaf-peepers and outdoors lovers who are looking to extend the season should consider Connecticut. By the second week of October or so, when the leaves are already falling fast from the trees up north, Connecticut’s trees are just beginning to burst into those sought-after shades of yellow, orange, and red. And while the elevation of hikes in southern New England may not reach the same kinds of heights as those in the northern states, the journey up and along hiking trails in Connecticut is just as beautiful. Here are five of our favorite hiking trails in Connecticut to tackle in the fall (or, hey, any time of the year).

5 Great Hiking Trails in Connecticut

Looking for hikes in southern New England? We think these five hiking trails in CT lead to some of the best fall foliage views around.

Mattabesett and Mount Higby Trail | Middlefield, CT

Distance: Nine miles round-trip
Rating: Moderate
About: Hike the Mattabesett Trail for some of the best views of the Quinnipiac Valley you’ll find in all of central Connecticut. While the Mattabesett Trail itself is 50 miles long, this hike up Mount Higby is less than 10 miles out and back. It features steep climbing and some rocky scrambling, and leads to ledges with beautiful overlooks. You’ll find wildflowers and towering trees along this well-maintained trail, marked with blue blazes.

Bear Mountain Trail | Salisbury, CT

Distance: Six-mile loop
Rating: Moderate
About: If you’re looking for the best views of fall foliage, heading to Connecticut’s highest peak (2,316 feet) is a good bet. The relatively long and steep hike, which starts from the Undermountain Trail parking lot, eventually rewards hikers with one of the prettiest vistas in the state, with mountain views to the north, south, and west and lake views to the east. The trail follows a section of the famous Appalachian Trail.

St. Johns Ledges and Caleb’s Peak | Kent, CT

Distance: Four miles round-trip
Rating: Difficult
About: If you’re willing to tackle a very rocky hike, the routes to St. John’s Ledges and Caleb’s Peak in Kent offer breathtaking views of the Housatonic River Valley. The 1.5-mile ascent to St. John’s Ledges, located on the Appalachian Trail, is strenuous but levels off at a lovely overlook of the valley. From there, hikers seeking views from even higher up can tackle the ascent to Caleb’s Peak (1,160 feet).

Talcott Mountain Yellow Trail | Bloomfield, CT

Distance: Three miles round-trip
Rating: Easy to moderate
About: While Talcott Mountain State Park has plenty of trails for all skill levels, the Yellow Trail is one of the most popular paths up to the 165-foot Heublein Tower. The steady climb leads to a spectacular view of the Farmington River Valley, with the 360-degree views from the tower stretching as far as Mount Monadnock to the north and Long Island Sound to the south.

Jessie Gerard Trail | Barkhamsted, CT

Distance: 3.5-mile loop
Rating: Moderate
About: Located in the 3,900-acre People’s State Forest, the Jessie Gerard Trail features stone steps, challenging climbs, rocky cliffs, gorges, dense forest, and, ultimately, breathtaking views from the Grand Vistas. Travel farther north and take in more incredible Connecticut views from Chaugham Lookout.

Do you have favorite hiking trails in Connecticut? Let us know!

This post was first published in 2018 and has been updated. 

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