Litchfield, Connecticut, is Lovely for Leaves

Litchfield CT Fall Photo
Kim Knox Beckius

Litchfield, Connecticut, makes a perfect fall foliage home base for travelers who want to experience autumn's glory in western New England. Here is a quick guide to the town of Litchfield, Connecticut, including accommodations, dining, nearby scenic drives, local attractions, fall day trip ideas, fun fall festivals and events and other essential travel information to help you enjoy autumn in the Litchfield Hills.

Location and When to Go

The historic town of Litchfield, Connecticut, settled in 1721, is located in northwestern Connecticut at the intersection of Routes 202 and 63. It is about a 2-1/2-hour drive from Boston, 2 hours from New York City or Albany, New York, and an hour from Hartford, Connecticut. The closest airport is Bradley International Airport in Windsor Locks, Connecticut. Fall colors can usually be observed during most of the month of October, with peak likely to occur around mid-month.

Fall Appeal

The town of Litchfield is set amid the rolling Litchfield Hills, foothills of the Berkshire Mountains that provide a vibrantly colorful backdrop for autumn activities. Litchfield melds both history and cosmopolitan flair. Its quintessential town green dates to 1723, and nearby, you'll find both historic structures and upscale boutiques and restaurants. A fall visit to Litchfield puts leaf peepers in the heart of a region noted for scenic driving, hiking, biking, antiquing, wine tasting and more.

Places to Stay

Just a bit outside of town, you'll find country lodging and dining at the Toll Gate Hill Inn & Restaurant. The Litchfield Inn also provides convenient access to all of the enticements in and around Litchfield. For the ultimate in exclusivity and privacy, book one of the individually designed cottages at Winvian, where you can even sleep in a treehouse or under a woodland canopy. Rates are exorbitant for popular fall weekends, but midweek stays can be an affordable indulgence. Compare rates and reviews for hotels and inns in the Litchfield area with TripAdvisor.

Nearby Scenic Drives

During fall foliage season, scenic driving is one of the Litchfield area's lures. I love to drive along the shores of picturesque Lake Waramaug in nearby New Preston, Connecticut. Heading north to the covered bridge in West Cornwall, then south on Route 7 past Kent Falls to Kent, another charming New England town, is also a beautiful way to spend a fall day. The Litchfield Hills Visitors Bureau provides several themed driving tours for travelers to follow.

Local Attractions

While you're in Litchfield, tour the Tapping Reeve House, America's oldest law school; enjoy daily wine tastings at Haight-Brown Vineyard; learn more about this historic town at the Litchfield History Museum; see the leaves from above in a hot air balloon with ​Aer Blarney Balloons; walk the Labyrinth at Wisdom House; find gardening inspiration at White Flower Farm; or enjoy the outdoors at ​Topsmead State Forest, Mount Tom State Park or the White Memorial Conservation Center.

Within Three Hours

If you'd like to take day trips from Litchfield, there are many wonderful places to visit in the fall including Naumkeag, Chesterwood and the Norman Rockwell Museum in Stockbridge, Massachusetts; the Bennington Battle Monument and Robert Frost's gravesite in Bennington, Vermont; ​Lake Compounce, America's oldest amusement park in Bristol, Connecticut; the scenic and cultural attractions along Massachusetts' Mohawk Trail; and Frederic Church's Olana in Hudson, New York.

Dining Delights

In Litchfield, popular dining choices include West Street Grill and Litchfield Saltwater Grille. Find top-notch farm-to-table cuisine at Arethusa al tavolo in Bantam or Community Table in Washington, both a short drive away. In nearby New Preston, I recommend the Hopkins Inn Restaurant both for wonderful food and beautiful fall views of Lake Waramaug. Visit the ​wine bar at Hopkins Vineyard next door before or after your meal. The Litchfield Hills Visitors Bureau provides additional dining listings.

More Fall Fun

There's more fall fun near Litchfield: attend the annual Garlic & Harvest Festival held in October at the Bethlehem Fairgrounds; take a pumpkin patch train ride at the Danbury Railway Museum, or book passage aboard the Naugatuck Railroad and view fall foliage along the Naugatuck River on a leisurely train ride.

Request a free Litchfield Hills brochure online or by calling the Western CT Visitors Bureau at 860-567-4506.

Was this page helpful?