The Best Lesser Known Hiking Trails

May 3rd 2024

The Best Lesser Known Hiking Trails

Enjoy the peace and quiet of these hidden-gem trails in CT and beyond.

Hiking is great year-round, but some of the more popular state parks and hiking areas have packed parking lots and busy trails where it feels like a never ending parade of people. If you like to head out in nature for peace and serenity, rest assured, there are plenty of places for you to hike. These are the best lesser known hiking trails to get your nature fix while avoiding crowds.

Our Favorite Lesser Known Hikes In Connecticut

Macedonia Brook Loop - Kent

This challenging, 6.8-mile loop trail inside Macedonia Brook State Park is in an area popular for backpacking, camping and hiking, but this trail still manages to be relatively quiet. This trail meanders along beautiful streams and has boulder scrambles and a ridge walk with amazing views. If you’re hiking counterclockwise, you’ll encounter the scramble in the first mile. On a clear day, you can see up to the Catskills.

Trailhead Parking: 159 Macedonia Brook Rd, Kent, CT 06757

Route: Macedonia Brook Loop

Dividend Pond and Falls - Rocky Hill

This quiet hike is located in the heart of Rocky Hill just 15 minutes south of Hartford. The 0.4-mile loop goes around Dividend Pond, but you can easily tack on miles using other trails in Dividend Pond Open Space. The best part is the scenic waterfall at the west end of the loop.

Trailhead Parking: Old Forge Rd, Rocky Hill, CT 06067

Route: Dividend Pond and Falls

Canaan Cliffs - Falls Village

If you’ve ever driven Route 7 between North Canaan and Falls Village, you’ve driven by these secret trails. There are a bunch of trails hidden in the hills here, and the secret, west-facing cliffs promise views for miles. The route is short–just 3.2 miles out and back, but you’ll get 1,000+ feet of elevation in the first 0.7 miles through a series of switchbacks. Be sure to download a map before you go, because this route intersects with a bunch of other trails, and since the service can be spotty, it’s easy to take a wrong turn.

Trailhead Parking: 420 S Canaan Rd, Falls Village, CT 06031

Route: Canaan Cliffs

Ives Trail and Greenway - Danbury

We love a longer trail because it gives you the chance to pick your own adventure. The Ives Trail Greenway is 15.2 miles out and back, so you can hike the entire distance or turn around at any point for a shorter trek. You’ll get some nice views of lakes, ponds and nearby Pine Mountain. It’s generally considered a challenging hike and it’s popular, but you can still catch some solitude if you hike mid-week.

Trailhead Parking: 70 Southern Blvd, Danbury, CT 06810

Route: Ives Trail and Greenway

Van Sinderen Loop - Washington Depot

Hidden Valley Preserve is home to the Thoreau Bridge, a cable-stayed, mass-timber suspension bridge spanning 134 feet that connects the northern and southern portions of the 700-acre preserve. The Van Sinderen Loop is a 3.4-mile trail that is moderately challenging. It crosses the bridge, so you don’t have to go looking for it. This is a popular trail for hiking and running, but you can still enjoy some solitude during quieter times of day. It’s easy to tack on extra miles using some of the trails on the east side of the preserve off Sabbaday Lane.

Trailhead Parking: 198 Bee Brook Rd, Washington Depot, CT 06794

Route: Van Sinderen Loop

Other Lesser Known Hikes We Love

We love hiking in Connecticut, but exploring new states on foot is so fun. These are a few hidden gems in the Northeast, Southeast Midwest and West that we love. From a quick loop outside of a major New England city to backcountry trails in a national park and a remote hike in the Colorado Rockies, there’s something for everyone.

Tucker Hill Green Dot Loop Trail - Massachusetts

This trail is part of a large system of trails in Blue Hills Reservation just west of Boston. It’s a great way for city folks to get a dose of green space, and plenty of people do! But, because there are so many trails in Blue Hills, it’s really easy to pick one to have all to yourself. The Tucker Hill trail is a 2.9-mile loop that crosses a handful of other trails. Hikers are asked to travel counterclockwise which is probably why it feels so quiet–people are ahead of you or behind you instead of crossing paths with you. You can easily tack on extra miles if you want to see other people or go longer, and some of them are quite challenging! If you add a section of the Skyline Trail to the top of Tucker Hill, you can see Boston’s skyline on a clear day.

Trailhead Parking: 695-821 Hillside St, Canton, MA 02021

Route: Tucker Hill Green Dot Loop Trail

Sal Hollow and Buffalo Creek Loop Trail - Kentucky

Nestled in the backcountry at Mammoth Cave National Park is this gentle, 5.4-mile loop trail. You’ll need park entry to get to it, and you’ll have to take the Green River Ferry (which is tiny and feels sketchy, but is perfectly safe!) to get to the parking area. Lots of people camp and hike in the Mammoth Cave backcountry, but you might end up feeling like the only person on the planet as you stroll this trail. It can get buggy and muddy after rain, and this trail is used by horseback riders… so watch your step.

Trailhead Parking: 920 Maple Springs Loop, Mammoth Cave, KY 42259

Route: Sal Hollow and Buffalo Creek Loop Trail

Prairie Fire Loop and Davis Trail Loop - Kansas

Kansas is one of those states that feels like it takes forever to drive through. Completely off the beaten path is Tallgrass Prairie National Preserve, a quiet little stop off Route 177, two hours west of Kansas City. This 10.1-mile loop trail is considered easy despite its length. It’s great for birding, and you’ll likely see bison while strolling the grasslands.

Trailhead Parking: 2480B KS-177, Strong City, KS 66869

Route: Prairie Fire Loop and Davis Trail Loop

Rogers Pass Lake via South Boulder Creek Trail - Colorado

Nestled in Colorado’s Rocky Mountains is this challenging, 8-ish-mile mountain trail that follows South Boulder Creek up to Rogers Pass, near the top of Haystack Mountain. This hike is very remote, and it’s best for experienced hikers. You’ll want to bring plenty of water and snacks, plus the Ten Essentials. Don’t forget bug spray–mosquitos are brutal in the early miles on this trail. The trailhead parking area fills up very early, but hikers tend to spread out along the trail, so eventually you’ll be alone. The incredible views at the top are worth the effort, and you’ll probably see a few people milling around and camping. If you keep following the trail past Rogers Pass Lake, you’ll get to Heart Lake for more amazing views. When you’re done,

Trailhead Parking: Co Rd 16, Nederland, CO 80466

Route: Rogers Pass Lake via South Boulder Creek Trail

Check out our blog for more tips to help you take the trail less traveled.