Connecticut Fall Foliage Adventures: Scenic Drives and Hikes

Long drives on winding country roads have always been a fall family tradition for us. The colonial houses, historic towns, rambling stone walls, classic old barns, sprawling horse farms, local farm stands…it's amazing what you can find on a drive! We've rounded up a list of our fave Fall foliage drives in Connecticut (and some suggestions for things to do along the way)! 

Here are our top picks…

Litchfield Hills Drive: Nestled in the northwestern corner of Connecticut, this scenic drive takes you through some of the most picturesque towns and countryside in Connecticut. A journey through winding roads, and charming small towns. Kent, Washington, and Cornwall dot the route, showcasing historic covered bridges and picturesque farmsteads framed by the colors of fall. 

Kick off your drive in New Milford and follow Route 67 through the picturesque towns of Bridgewater, Roxbury, and Washington. The drive offers stunning views of rolling hills and colorful foliage, as well as charming New England towns with historic homes and farms.

Mohawk Trail, Cornwall, Connecticut: This route winds through the rugged and scenic landscapes of Connecticut's northwest corner. Kickstart your adventure in Cornwall and let the road lead you along Route 4, guiding you through the picturesque towns of Goshen, Litchfield, and Torrington. This scenic drive offers stunning views of Fall foliage, as well as historic sites and state parks.

Housatonic Valley Heritage Loop: Start in New Milford and follow Route 7 north through Kent and Sharon. The drive takes you through charming towns and countryside, and offers plenty of opportunities to stop and take in the scenery.

Essex, CT: We love heading up to Essex for lunch at The Griswold Inn before doing some leaf peeping!  From Essex, you can head north or south along Route 154, both directions offering beautiful views of the river and the surrounding Fall foliage. The Essex Steam Train also has incredible fall foliage tours! 

Westport to Easton, Route 136: Route 136 ends close to Devil's Den Preserve, which is one of our fave spots for a Fall hike! Get lost on back roads in Easton...and stop in for brunch at The Olde Blue Bird Inn! 

Connecticut River Valley: Start in Middletown and follow Route 9 south to Route 154. You’ll pass through Haddam along the Connecticut River Loop. 

THE BEST FALL HIKES IN CONNECTICUT:

• Devil’s Den - Weston: Is Fairfield County’s largest preserve. With over 1,700 acres and about 10 miles of hiking trails, this is one of our go-to hiking spots!

• Sleeping Giant - Hamden: Great high altitude hike that rewards you with impressive panoramic views! Personal fave. 

• Chapman Falls @ Devil's Hopyard State Park- East Hamden: This 1,000-acre park offers great hiking, fishing, bicycling, picnicking, and camping. But don't miss the .5 mile Chapman Falls Loop! 

• Scalzi Park - Stamford: This is a cute little park just north of downtown Stamford. A great easy escape from the city.

• Mianus River Trail - Greenwich / Stamford

• Haystack Mountain - Norfolk 

• Orenaug Park Fire Tower -  Woodbury: Experience Woodbury's beauty with a delightful hike to a breathtaking fire tower viewpoint. The easy trail gently ascends to the tower, offering panoramic views when you climb the stairs to the top. Enjoy stunning cliffside vistas along the way.

• Bull's Covered Bridge - Kent Falls State Park: Drive down a one-lane road that passes through a charming 1842 wooden covered bridge, revealing lovely water views of the Housatonic River below. Hiking trails offer opportunities to explore waterfalls and rapids, but don't miss the equally stunning vistas from the road and bridge.

• Putnam Park - Redding: If you're looking for the perfect place to enjoy a leisurely walk while the leaves begin to change, you've found it! The loop trail, spanning just under a mile, offers a delightful stroll through well-maintained paths. What makes this place truly special is the touch of history that graces every step of your journey.