Savor the Best of Fall in Connecticut with These Leaf “Pairings” Last Updated 10/18

You’ve heard of wine pairings, well, in Connecticut, we’ve got a few “leaf pairings” for you— tips on experiencing the dramatic and diverse foliage of a Connecticut fall while enjoying a few great autumn activities. For the best viewing times, use our Foliage Finder to see when color is expected throughout the state. Then, enjoy your foliage with …

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A Spectacular View

High above the Connecticut River, there’s a unique, and some would say unusual, architectural marvel. East Haddam’s Gillette Castle was built in the early 20thcentury by celebrated actor William Gillette, who wanted to create a very real home for his most famous fictional persona, Sherlock Holmes. You can tour the inside of Gillette Castle at certain times throughout the summer and for special events like Christmas.  But it’s the grounds surrounding the castle, including trails, trestles, tunnels and even a narrow gauge railroad, that really wow—especially in fall.

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A Fine Vintage

When the temperatures dip and the air is crisp, you may be tempted to snuggle inside. But many of Connecticut’s vineyards are still offering a tours and tastings well into the fall season. Some offer even more. At Chamard’s 40-acre vineyard along the Connecticut shoreline, fall color hits later in October, which is also a great time for a visit and a meal by the fire at their French-inspired Bistro.

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A Peaceful Paddle

Litchfield’s White Memorial Foundation is the state’s largest nature center at 4,000 acres for hiking, mountain biking, fishing, canoeing and more. At the Conservation Center Museum, you’ll also find year-round programs, walks and talks that really help to embrace the natural beauty of the preserve. Bring your own canoe or kayak and drift through the spectacular fall foliage that surrounds you.

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A Roaring Firepit

After a day touring Connecticut’s “Quiet Corner”, share your memories around the firepit at Woodstock’s Mansion at Bald Hill. This premier bed & breakfast also offers fine dining and a scenic spot for weddings and other gatherings. Book an overnight stay and experience the drive on Connecticut’s famed Route 169, which winds its way north-south through Connecticut’s scenic eastern region.

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A Little College Spirit

New Haven’s Yale University isn’t just one of the top educational institution s in the world. It’s also home to an amazing array of cultural destinations, historic sites, art museums and some of the hottest restaurants in New England. It’s a worth a visit any time of year. But the fall lends a particular air of academic grandeur as the tree-lined walkways and the parks in the Elm City change their colors. Experience the best of fall as you mingle with students rushing to class, tailgate a game at the Yale Bowl or linger in one of the many museums and theaters.

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Small Town Charm

One of the best ways to really experience fall in Connecticut is to spend a little time in one of the many picturesque small towns around the state, and Essex is postcard-perfect for a day or a weekend of fall foliage viewing adventures. From here you can travel back in time on a vintage steam train, browse boutiques and art galleries or even see the color from a riverboat on the Connecticut River itself.

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A Beautiful Bike Ride

Seeing the leaves from within is the perfect way to enjoy fall and get a great workout too. Many of Connecticut’s hiking trails are also open to bike riders. Grab your mountain bike and take a ride on Haley Farm State Park’s 7½ mile bikeway from Mystic to Groton. If you’re looking to take your bike out on the trail in another part of Connecticut, you’ll find a list of recommended rides, here.

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A Waterfall View

After the rains of summer, Connecticut’s waterfalls really show their stuff. Pack a lunch and take a short hike to experience natural beauty at its most extreme. The one in Devil’s Hopyard State Park is particularly stunning in fall. Other great spots for waterfalls include Kent FallsYantic Falls (or Uncas Leap Falls) in Norwich and Indian Well State Park in Shelton.

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A Work of Art

What better way to experience the beauty of fall than from an inside-out perspective? The Philip Johnson Glass House in New Canaan is a historic site that invites you to enjoy a one-of-a-kind architectural masterpiece surrounded by acres of amazing fall color. Whether you arrive by car or by train via Metro-North, the town of New Canaan itself offers classic a New England fall main street experience, with shops, restaurants and more.

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Your Best Friends

Sometimes, all you need to enjoy the fall foliage is a big rock and your best friends. You’ll find great views of New Preston's Lake Waramaug when you pick up the trail in the Maricrostas Preserve and hike to the pinnacle. There are hiking trails all across the state, and you can find a few of them, here.

When it comes to experiencing fall in Connecticut, there’s so much more where this came from.  Find more of Connecticut’s great fall getaways now!