Litchfield County, Connecticut
Looking for the best hiking in Litchfield County? We've got you covered with the top trails, trips, hiking, backpacking, camping and more around Litchfield County. The detailed guides, photos, and reviews are all submitted by the Outbound community.
Top Hiking Spots in and near Litchfield County
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Simsbury, Connecticut
Hike to the Heublein Tower on Talcott Mountain
4.32.54 mi / 404 ft gainThe Heublien Tower Trail, located just inside the Talcott Mountain State Park entrance off of Route 185 in Simsbury CT, is a short 1.25 miles. While the hike isn't long, the first 1/3 of a mile is a steep incline that will get your heart pumping. The trail itself it very well kept, and although ...Read more -
Mount Washington, Massachusetts
Explore Bash Bish Falls
4.21 miOne of my favorite walks to a spectacular falls. The trail is easy to follow and one mile from NY parking lot and 0.5 from the parking lot. The apparent place to swim. There are several very nice, family safe swimmable pools in the creek above and after the falls. There are signs at the top of t...Read more -
Berlin, Connecticut
Hike the Ragged Mountain Memorial Preserve
4.55.5 mi / 560 ft gainRagged Mountain main loop is approximately 5.5 miles long, and is known for its expansive bare-rock vistas, vertical cliff faces, and scenic views overlooking cliff-side reservoirs and ponds. The trail is rated moderate, with some flat stretches among the trees, mixed with some uneven rocky foot...Read more -
Cheshire, Connecticut
Hike to Roaring Brook Falls
1.2 mi / 377 ft gainArriving to the falls, parking is residential but don't worry everyone is friendly. Starting off the hike you will walk past a cool pond where you may be able to see some wildlife. Continuing on, you will follow the marked trail where it will take you further into the woods while gaining elevatio...Read more -
Meriden, Connecticut
Hike the Metacomet, Blue, and Yellow Loop
5.04.5 mi / 976 ft gainStart from the Castle Craig road entrance. Walk until you're greeted by a beautiful reservoir. You'll notice the strange but beautiful Mine Island in the middle of all this. You'll also notice markers for White Trails and Yellow Trails. The White Trail is an easier/wider trail. The Yellow Trail C...Read more -
Great Barrington, Massachusetts
Mt. Wilcox and Beartown Mountain Trail Loop
5.09.29 mi / 981 ft gainMt. Wilcox and Beartown Mountain Trail Loop is a loop trail that takes you by the lake located near Great Barrington, Massachusetts.Read more -
Danbury, Connecticut
Hike Middle Mountain To Thomas Mountain Loop
3.7 mi / 856 ft gainMiddle Mountain to Thomas Mountain Loop is a 3.7 mile loop hike that takes you past great forest setting located near Danbury, Connecticut.Read more -
Great Barrington, Massachusetts
Hike Monument Mountain
4.02 mi / 720 ft gainAt 1642 feet (with a total elevation gain of 720 feet), Squaw Peak is a great spot to see both Mt Greylock along the Vermont border, and the Catskills in New York. There are several trail options here to get to the summit, but no matter which combination you choose, you can keep your trip under ...Read more -
Hamden, Connecticut
Hike the Tower Trail to the Blue Trail at Sleeping Giant SP
5.03 mi / 518 ft gainSleeping Giant State Park is a place very close to my heart. I spent 4 years right across the street at Quinnipiac University and have hiked “The Giant” more times then I can count and at all different hours. There are a few different trails you can explore but my favorite one is up to the cliffs...Read more -
Hamden, Connecticut
Hike the Mill River Trail to the Blue Trail at Sleeping Giant SP
5.03 mi / 518 ft gainSince I was a child, I’ve always enjoyed hiking the Giant. As Connecticut parks go, this terrain is some of the most challenging (and unfortunately, the most dangerous) in the state. The actual ridge is approximately 2.75 miles long by 1.75 miles wide, and offers approximately 24 miles of hiking ...Read more -
Hamden, Connecticut
Boulder & Free Climb off the Blue Trail In Sleeping Giant SP
Sleeping Giant State Park does not just have great hiking, it also has great climbing and bouldering. Pick up the blue trail starting at the backside of the visitor center. This trail climbs pretty steadily but take note that as you hike up the cliff below you is a great spot to checkout for boul...Read more -
Meriden, Connecticut
Higby Mountain Trail
2.11 mi / 486 ft gainThe popular route for this hike is to park your car at the base of the trail which is located right before merging onto 91-S in Middlefield, CT. The parking lot does seem to get crowded mid-day, especially if the weather is nice! The beginning of the hike is mostly flatter land and an incline w...Read more -
Ridgefield, Connecticut
Hike the Hemlock Hills & Pine Mountain Loop
7.5 mi / 1174 ft gainThere are several trailheads for Hemlock Hills But the least crowded is at the intersection of Ned's Mountain road and Bogus Road. I took my 3 year old black lab. There are ton's of little ponds for your dog to jump in and do dog things. For the most part the hike is flat but at some parts it c...Read more -
Carmel Hamlet, New York
Ninham Mountain Fire Tower
5.01.23 mi / 367 ft gainThis is more of a stroll than a hike, which is nice because you can add it to another hike in the same day if you're in the area. From the dirt parking lot take the trail off to the right. Just stay straight and in about 15 minutes you'll see a huge fire tower (hard to miss). Feel free to climb a...Read more -
Stockbridge, Massachusetts
Laura's Tower and Ice Glen
5.02.4 mi / 676 ft gainYou will park at the end of Park Street in Stockbridge, Massachusetts. From the parking are you will cross a beautiful bridge over the Housatonic River. The trail crosses railroad tracks and immediately begins to climb into the woods. You will reach a split in the trail, a left will take you...Read more -
Middletown, Connecticut
Explore Wadsworth Falls
5.00.25 miWhen it comes to exploring Wadsworth Falls its ease of access couldn't be better. As soon as you pull into the parking lot you hear the falls roaring. Take the quick walk to see the picturesque scenery.Facts about Wadsworth Falls:Height: 25ft tall and doubled in width Rock: Hampden Basalt -the ro...Read more