Top 10 Fun Things To Do in Connecticut During Fall

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As the Nutmeg State unveils its vibrant autumn palette, there’s no better time to immerse yourself in some quintessential New England charm. With the longest fall foliage season in New England, starting in late September and extending to early November, charming Connecticut becomes a haven for fall enthusiasts. 

In this blog post, I’ve curated a list of my favorite fall activities in Connecticut that will allow you to enjoy the breathtaking fall colors while experiencing the timeless charm of a New England favorite. From scenic drives to small towns and fall festivals, discover what sets Connecticut apart during fall and why so many people leave, always wanting to return.

Go For a Scenic Drive

Scenic drives are one of my favorite fall activities. Connecticut has no shortage of scenic drives all over the state that become more alive when the leaves burst with red, orange, and yellow hues. The best

Route 136, or Tokeneke Road, is perfect for scenic views. This road goes from Darien to Westport and will eventually lead you to a coastal area known as Rowayton – you’ll get lovely waterfront views and seafood restaurants while you’re here. 

The Litchfield Hills Scenic Drive is another great option. This 58-mile loop leads you through some of the most famous landmarks in Connecticut, including the Appalachian Trail, Housatonic River, and Bull’s Bridge. You can also take a detour from this drive to stop at White Memorial Conservation Center or Kent Falls State Park. 

Visit a Fall Farm

From corn mazes and apple orchards to bumpy hayrides and pumpkin patches, there is no better way to experience Connecticut in fall than at a farm. Check out Lyman Orchards for an impressive pumpkin selection, delicious apple cider donuts, and a challenging corn maze. Whittle’s Willow Spring Farm is another fantastic fall farm with pumpkin picking, apple picking, and fresh produce.

If you want to meet a few animals, check out Silverman’s Farm, which has a petting zoo, pick-your-own-apples, and a country store with fresh produce, cheese, bread, and pies.

Strawberry Hollow Farm is another favorite, with the most aesthetically pleasing storefront and gift shop of curated goods with candles, ornaments, and specialty foods.

Go Leaf Peeping in a State Park

Start at Pachaug State Forest, the largest forest in the Connecticut state forest system, with over 27,000 acres of green space. As you can imagine, this park has seemingly unlimited hiking opportunities!

For an incredible mountaintop lookout, head to Talcott Mountain State Park. This 574-acre park is home to the Heublein Tower, a 165-foot-high tower on top of a mountain – you’ll see stunning foliage for miles. 

Macedonia Brook State Park is beautiful in the fall, with over 2,300 acres of foliage and the Macedonia Ridge Trail, where you can hike through Cobble Mountain and other peaks.

Other great places for leaf peeping in the Nutmeg State include the Mohawk State Forest, Dennis Hill State Park, and Shenipsit State Forest.

Go For a Hike 

While you’re exploring all of those incredible Connecticut state parks, lace up your boots and go for a hike. Late September or early October is the best time to see the trails adorned with peak foliage. 

Start at the Jessie Gerard Trail, located in Peoples State Forest – this three-mile loop features a picnic area, a scenic overlook, and beautiful waterfalls. The Chauncey Peak Trail, found in Giuffrida Park, is a little shorter at around two miles. However, it’s got a steep incline, so wear some shoes with good traction.

As I mentioned before, Heublein Tower in Talcott Mountain State Park is the best spot for scenic views. This observation tower showcases the Hartford skyline and the Farmington River Valley, which is especially beautiful in the fall.

Enjoy a Ride on the Essex Steam Train

Located in Essex, Connecticut, the Essex Steam Train is one of the best experiences for scenic views during the fall season. This train ride begins at the 1892 Essex Station, where you’ll embark on a 12-mile narrated journey through the stunning Connecticut River Valley. 

You’ll have the option of taking a 2.5-hour combined train and riverboat ride, or a 1-hour train-only experience. Along the way, enjoy views of quintessential New England towns like Chester and Deep River. You can also opt for first-class seating on the train to enjoy a window seat and beverages.

Take a Scenic River Cruise

Enjoy a scenic river cruise on the Connecticut River to view the Connecticut River Valley’s gorgeous autumn scenery. This boat ride will showcase Joshua Rock, Hamburg Cove, Essex Harbor, and small towns like Lyme, Old Lyme, and Deep River. You might even see some wildlife along the way, like a Bald Eagle or Osprey – bring your camera or binoculars just in case!

Stroll Through a Small Town

Connecticut is known for its adorable small towns, and exploring them in the fall will make you feel like you’ve stepped onto the set of Gilmore Girls.

New Haven is a great place to start for New England charm – home to the world-renowned Yale University. Stop into the Peabody Museum of Natural History, the Yale University Art Gallery, or the New Haven Museum. When you get hungry, head to Little Italy for delicious pizza and pasta.

Mystic is another must-visit Connecticut small town located on the Mystic River. While you could stroll along the waterfront and enjoy a beautiful fall day, you could also stop into the Mystic AquariumMystic Museum of Art, or the Mystic Seaport Museum – there’s plenty to do in this small town.

Wethersfield, Connecticut, is an adorable town that is especially cozy during the fall months. Historic colonial architecture makes this a fun place to walk around, and you can also check out the Webb Deane Stevens Museum for a dose of history. 

Stroll down Kent, Connecticut’s historic Main Street, and explore the shops, art galleries, and restaurants. There are also several hiking trails in this area where you can view more fall foliage, or visit Bull’s Bridge, a historic covered bridge perfect for photo opportunities.

Get Cozy With Warm Apple Cider

There’s no better way to warm up in autumn than with a cup of hot and fresh apple cider. While there are plenty of places to grab hot cider in Connecticut, B.F. Clyde’s Cider Mill, near Mystic, is one of the best – this is the oldest steam-powered cider mill in the country!

In addition to standard warm apple cider, you can enjoy treats like old-fashioned cider donuts, apple turnovers, cider slushies, and baked apple pie. You can even sample hard cider and wines like Apple Raspberry, Blueberry Spinner, Goodfella, and Strawberry Bliss.

Visit Gillette Castle

Located in Gillette Castle State Park, Gillette Castle is perched right over the nearby river, so the views from the top are stunning during the fall. Tour the castle to view the ornate woodwork, 47 unique doors, and built-in furnishings. Stroll the grounds to enjoy walking paths with stone-arch bridges, wooden trestles, and a goldfish cellar. These grounds are gorgeous in autumn while in a blanket of crimson, gold, and green leaves.

Enjoy a Fall Festival

There’s nothing quite like the autumn festivals you’ll find in Connecticut in the fall – it seems like every town has one of its own!

If you’re bringing the whole family, you can’t go wrong with the New Canaan Harvest Festival. Enjoy cider press demonstrations, old-fashioned games, kids’ crafts, and a pumpkin scavenger hunt. 

The Kent Fall Festival is another crowd-pleaser – and because Kent is so adorable in the fall, this event is one of the best. This festival showcases working farm equipment, a blacksmith shop, and, of course, fall food and local vendors. 

The Glastonbury Apple Harvest & Music Festival is more about the music than the apples. Enjoy shows from local artists and indie musicians while sampling class fair food and food truck eats. The kids will also enjoy the variety of carnival rides at this event!


New England is the best area to visit for outdoor lovers and small-town. The quaint towns are nestled amongst colorful forests, offering a range of outdoor activities. Whether it’s a fall foliage road trip or a weekend getaway, you won’t regret visiting Connecticut in fall.

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