Kent, Connecticut offers an authentic escape where historic covered bridges quietly stand against the backdrop of fierce autumn foliage. This hike traces a roughly 5.5-mile loop through forested terrain with a moderate elevation gain of 700 feet—enough to engage your muscles without overwhelming your stride. The trail’s dirt and leaf-carpeted paths crunch underfoot, while hardwood trees around you flicker in shades of amber and crimson, their branches swaying as if whispering ancient stories.

Begin at Bull’s Bridge, where the covered wooden structure dares you to cross its weathered planks. The nearby Housatonic River pushes forward relentlessly, its currents adding a lively soundtrack to your trek. Follow the river upstream as the trail veers into deeper woods, where sunlight filters through a canopy of maples and oaks playing with the light. Each step climbs gently, rewarding you with occasional peek-a-boo views of the river’s shimmering ribbon below.

Mid-hike, pause at Bull’s Bridge Falls, a silent cascade that mirrors the fiery colors overhead. The terrain here tightens; roots and rocks invite careful foot placement. Stay alert but let nature draw your gaze—the rushing water seems to challenge your pace, encouraging a moment’s rest. As you continue, quiet fields open up, framed by the silhouettes of graceful covered bridges, each a reminder of Kent’s thoughtful preservation of history.

Timing your hike for mid to late October guarantees the peak of fall’s bold palette. Bring sturdy boots with good traction—wet leaves can cloak slippery patches—and pack water to stay hydrated along the steady climb. The trail’s length suits a half-day adventure, leaving time to savor local fare in Kent village afterward.

Kent embraces autumn as a living, breathing presence. The bridges stand firm against the seasonal shift, the trees flaunt their fiery personalities, and the river carves a steady course beneath it all. This hike offers not just a walk but an active conversation with Connecticut’s rugged creativity and calm endurance, ready for anyone who respects the challenge without fear.