Best Connecticut Fall Foliage Hikes and Scenic Drives for 2025

🍂 Long drives down windy country roads have always been a fall family tradition for us. There’s just something about Connecticut in October… rambling stone walls framed by golden maples, barns tucked into rolling hills, and roadside stands stocked with apples, pumpkins, and mums. And while the views from the car are dreamy, nothing beats pulling over, lacing up your boots, and stepping right into the colors.

This season, we’re sharing our favorite Connecticut fall foliage adventures- a mix of scenic drives and hikes that capture the best of the season. Whether you’re looking for a quick local leaf-peeping fix or a full day trip to soak in those big autumn views, these are the spots we go back to year after year.

HIKES

Kent Falls State Park (Kent)

Kent Falls is the kind of spot that makes you remember why fall in Connecticut just hits different. A quick drive from Fairfield County, this park is home to one of the most stunning waterfalls in the state- and come October, the surrounding hillsides light up like a bonfire. The trail runs right alongside the falls… It’s easy enough for families, but still delivers those “wow” views. Insider move: get there on the early side. By midday on peak weekends, the parking lot (and the trail) fills fast.

Devil’s Den Preserve (Weston/Redding)

With nearly 1,800 acres to explore, you can spend an afternoon weaving through trails that feel worlds away from the busy suburbs. In October, the canopy above is glowing gold and crimson, and the trails underfoot are blanketed in crunchy leaves. If you’ve got time, head toward Prydden Brook and its hidden waterfall- it’s one of the preserve’s best-kept secrets. Bonus: it’s dog-friendly, so you don’t have to leave your furry hiking buddy at home.

Trout Brook Valley Reserve (Weston/Easton)

This preserve stretches across 1,000+ acres with almost 14 miles of trails that take you past old apple orchards, open meadows, and rocky ridgelines. We love it for the mix of mellow forest strolls and longer hikes with views, so you can pick your adventure. Pro tip: time your visit for golden hour, the light over the orchards is unbeatable.

Macedonia Brook State Park (Kent)

If your idea of the perfect fall hike includes views for days, head north to Macedonia Brook. The Blue Trail is the star here… it climbs up Cobble Mountain to views that are almost unreal. The full loop is a workout, but you can always shorten it and still snag those big-sky views. Pack a picnic… you’ll want to linger up top.

Mount Tom State Park Tower (Litchfield)

Mount Tom is the definition of short hike, big reward. In less than a mile you’ll climb to the park’s stone tower (built back in the 1920s) and suddenly have a front-row seat to one of the best fall panoramas in Connecticut. It’s quick, it’s easy, and it’s the kind of hike you’ll want to bring friends to just so you can see their faces when they hit the top.

Sleeping Giant (Hamden)

This one’s a true Connecticut icon. From a distance, the ridge looks like a giant stretched out for a nap… and the Tower Trail lets you climb right onto his “chest.” The hike is steady but manageable, winding through forests that absolutely glow in the fall. By the time you reach the stone lookout tower at the summit, you’ve got views that stretch across Quinnipiac Valley and beyond. 

Chapman Falls at Devil’s Hopyard (East Haddam)

Chapman Falls is fall magic with a side of local legend. The waterfall drops a dramatic 60 feet over sandstone ledges, surrounded by a forest that lights up in October. Look closely at the rocks- you’ll see round potholes carved into the stone. Some say the Devil himself stomped them in, but we like to think they just make for cooler photos. The trails are mellow, the picnic spots are plenty, and the soundtrack of rushing water makes this one of the most relaxing leaf-peeping day trips around.

Mianus River Park (Stamford/Greenwich)

Mianus River Park is one of those local gems that feels way more secluded than it actually is. Right on the border of Stamford and Greenwich, it’s super easy to get to but once you’re inside, the city feels miles away. Trails wind alongside the river, through quiet forests, and under a canopy that absolutely lights up in October. 

Scenic Drives

Route 15 - Merritt Parkway

If you’re looking for an easy, local go-to, the Merritt is unbeatable. With its historic stone bridges, winding curves, and tree-lined stretches, it’s one of the most scenic highways in the country. The best part? You can make a whole fall day of it by hopping off along the way. Swing through Easton to grab fresh-pressed cider at Silverman’s Farm, or detour into Shelton for pumpkin picking at Jones Family Farms. Keep rolling north and you can stretch your legs with a foliage-filled walk at Sleeping Giant State Park in Hamden before getting back on the Parkway.

Route 7 - Norwalk to Canaan

Route 7 is basically the fall foliage runway of Connecticut. Starting in Norwalk, it meanders north through charming towns like Wilton, Ridgefield, and Kent (don’t miss Kent Falls State Park while you’re there). The road winds along the Housatonic River, framed by glowing hillsides- classic leaf-peeping material.

Route 169 - Norwich to Woodstock

This is Connecticut’s official National Scenic Byway, and for good reason. The 32-mile stretch runs through historic villages, colonial churches, and quiet farmland. The drive is quintessential New England- rolling hills, stone walls, and trees bursting with every shade of autumn. Bonus: it feels a little less crowded than some of the western CT hot spots.

Route 154 - Old Saybrook to Haddam

Want some river views with your foliage? This stretch hugs the Connecticut River and delivers both. You’ll catch charming river towns like Essex (worth a pit stop for cider and a stroll) and gorgeous water views framed by bright fall color. It’s a slower, more meandering ride- perfect for a weekend drive with windows down and cozy playlists on repeat.