Think Connecticut can’t compete in the big leagues of leaf peeping? Don’t be so sure. Once mid-October rolls around, the Litchfield Hills burst with vibrant reds and oranges that (dare we say it) rival those of our neighbors to the north. Revel in the best of Connecticut fall foliage on this scenic byway full of popular leaf peeping pit stops near Lakeville.
Stop #1: Cobble Mountain Trail Overlook (Kent, CT)
Head south from Lakeville on the leisurely Route 41, a scenic state highway of pastoral landscapes and saltbox farmhouses. After a 30 minute drive, you’ll arrive at Macedonia Brook State Park in Kent. Grab a trail map at the front office and take to the white blazed Cobble Mountain Trail — the overlook offers a magnificent view across the Harlem Valley to the distant Catskills. It’s a spectacular sight year-round, but at the height of foliage season, those incredible colors are in a league of their own.
Stop #2: Bulls Covered Bridge (South Kent, CT)
Once you’ve had your foliage fix at the Cobble Mountain overlook, take a short detour to the Bull’s Bridge, which crosses the Housatonic River. The sight of this charming, classic New England covered bridge surrounded by oranges and browns is the thing of autumnal postcards. This also makes a great opportunity to set up a scenic fall picnic or venture into downtown Kent for a bite to eat.
Stop #5: Interlaken Inn (Lakeville, CT)
After another 20 miles or so of rolling hills and winding stone walls, you’ll be back in the quiet comfort of Lakeville. While we have plenty of places to peep leaves in the Litchfield Hills, at Interlaken Inn can you pull up an Adirondack chair and take in the views from your porch — all while scrolling through snapshots from your fall foliage tour in Connecticut.