09/30/2026
🍁 THE ULTIMATE CONNECTICUT LEAF-PEEPING DAY TRIP 🍂
Looking for a picturesque autumn getaway? The Litchfield Hills (Northwest Connecticut) offers the quintessential New England foliage experience—complete with historic town greens, winding rivers, covered bridges, and rolling wooded hills.
Best of all, you can take on this 100-mile scenic loop as an all-day family road trip, or pick and choose shorter segments for a quick afternoon outing!
📅 When to Go
Peak Foliage: Typically the 2nd and 3rd weeks of October.
Tip: The Litchfield Hills turn earlier than coastal areas, so plan your drive for mid-October to catch peak vibrance!
🚗 The Route & Key Stops
📍 9:00 AM — Litchfield Town Green
Start: Begin in historic Litchfield center. Grab a coffee and fresh pastries at a local café while enjoying the classic New England village architecture.
🚗 Drive: Take Route 63 North to Route 44 West through the rolling farmland of Goshen.
📍 10:30 AM — Mohawk State Forest (Cornwall)
Stop 1: Drive up or take a short scenic walk to one of the highest points in the area—perfect for early-morning panoramic photos.
📍 11:30 AM — West Cornwall Covered Bridge
Stop 2: Head south on Route 7, then take Route 128 East over the Housatonic River. This iconic red covered bridge is one of CT’s most photographed fall landmarks!
🚗 Drive: Follow legendary Route 7 South alongside the Housatonic River, passing past Housatonic Meadows State Park through dense canopy.
📍 1:00 PM — Lunch & Exploration in Kent
Stop 3: Arrive in the artsy village of Kent. Stroll local galleries, browse boutique shops, and enjoy lunch at a quaint local deli or restaurant.
📍 2:30 PM — Kent Falls State Park
Stop 4: Located just north of Kent center. Take the short, paved walk along cascading waterfalls framed by vibrant red and yellow foliage.
🚗 Drive: Head Route 341 East to Route 45 North for a drive around Lake Waramaug, famous for incredible foliage reflections on the water.
📍 4:00 PM — Hopkins Vineyard (Warren, CT)
Stop 5: Unwind with a w**e or c***r tasting on the hill overlooking Lake Waramaug and the surrounding autumn landscapes.
🚗 Drive: Complete the loop via Route 47 South to Route 202 East through Washington Depot and New Preston back toward Litchfield.
🚗 Flexible for Families & Day-Trippers: Drive the full loop or select 2–3 stops for a customized fall drive!
What is your favorite fall foliage spot in Connecticut? Drop your photos in the comments below! 👇
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