A Complete Itinerary for Fall Activities in Connecticut

When you live in a state where the only seasons are hot and hotter, you truly appreciate visiting New England in the fall, where cooler weather and fall foliage prevail.  We found so many fall activities in Connecticut that I just had to share. I hope they will captivate and entice you to visit the Constitution State.

Connecticut is one of six states that make up the New England region of the Northeastern United States. It was one of the original thirteen colonies and is the third smallest state in the United States. It is so tiny that it could fit into Texas around fifty times!

Its size makes it a perfect state to visit in a short amount of time. So, if you are limited on time but still want to see quintessential New England, consider visiting Connecticut.

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The Best Time to Visit Connecticut

The short answer is fall!

Connecticut is a wonderful place to visit in the fall. From the vibrant colors of the leaves and the crisp, cool air to the fun festivals and events that take place throughout the state, there’s a lot to love about autumn in Connecticut.

As you plan your trip, think about planning around the dates of some of these family-favorite festivals. They often include live music, family entertainment, and plenty of fall activities.

• Connecticut Renaissance Faire – Home to medieval-themed activities, live jousting tournaments, performances by jesters, an artisan market with handcrafted goods, period costumes, and interactive play
• Apple Harvest Festival This festival runs six days over two weekends from late September through early October. You’ll find parades and live music entertainment, a craft fair showcasing local artisans, and family-friendly activities.
• Connecticut Garlic and Harvest Festival Located in Bethlehem, this festival has cooking demonstrations by expert chefs, garlic growing seminars, a vendor market with garlic products, live music, and entertainment suitable for all ages.

Besides the fun festivals, the beautiful foliage begins to bear the fall colors during the autumn months.

You’ll also be able to take advantage of all the fall activities around the state, like apple picking, pumpkin carving, and hayrides, with some good old-fashioned autumn weather.

Driving through New England’s countryside is relatively easy, and the roads are easy to navigate.

Day 1 – Visit Mystic Country

Pick up your rental car and head toward Mystic, CT.

One of the best places to start your Connecticut trip is Mystic Seaport, which is located on the Mystic River in Mystic, Connecticut. There are many things to do here, such as taking a scenic cruise on the river or exploring the museum exhibits and buildings.

Spend the first part of your day exploring this charming seaside town.

Mystic is a quintessential New England town with a rich history and a great place to visit in the fall.

The harbor is beautiful at this time of year, especially when you’re standing on the Mystic drawbridge looking out over it.

Downtown Mystic has many shops, restaurants, and bars worth checking out during your stay. You can also walk along historic streets or ride bikes through town to get outside for some fresh air.

Eat at a Local Favorite

A fun, family-friendly restaurant is Mystic Pizza.

You may remember the spot from a popular movie of the same name starring Julia Roberts. This comfy restaurant, with both booths and tables, plays the movie on repeat while serving scrumptious pizza.

The Shipwright’s Daughter is a casual but upscale place to eat any time of the day. Recently named Restaurant of the Year by Connecticut’s Restaurant Association, it’s not hard to see why once you eat there.

The entire dining experience is top-notch, and the food is outstanding.

They recently began serving a breakfast buffet in the mornings. If the eggs benedict and french toast are any indications of the food on the buffet, I bet it will all be equally delicious.

Another great restaurant in Mystic is the S & P Restaurant and Oyster Bar. The outdoor patio area overlooks the Mystic Drawbridge with heaters near the tables for comfort.

You can order anything from the jumbo lump crab cakes to oysters on the half shell, or if you’re not feeling like eating seafood, try the pork chops.

Visit a Winery

There’s much to see and do in the Mystic Stonington area, but for a great place to relax and unwind, fall is a great time to visit the many wineries along Connecticut’s Wine Trial. I especially recommend visiting the Jonathan Edwards Winery.

Jonathan Edwards Winery is the perfect place to spend an afternoon on your first day in Connecticut.

The tasting room is in a restored 1880’s dairy barn, and the grounds are 48 acres of lush vineyards. Pick up a picnic from Mystic Market to enjoy on the grounds while you enjoy your tastings of award-winning wines.

Where to Stay in Mystic/Stonington

• Whaler’s Inn – This charming inn is right on Main Street in Mystic, near the drawbridge, shops, and restaurants.
• Private Stonington Home – This private rental is located in a historic home in Stonington. Every thing you could want is included in this rental right down to the bottle of water and chocolates left next to your bed.

Day 2 – The Best Fall Activities in Connecticut

Today’s itinerary is packed! First, you’ll stop at a cider mill for a hot cup of apple cider and delicious apple cider donuts. Then, it’s off to one of the many apple orchards in Connecticut.

Afterward, you’ll get lost in a fall corn maze.

You’ll ride an old-fashioned steam train around the backwoods of Connecticut on a historical excursion with our friends at the Essex Steam Train.

After that, you’ll end the day going pumpkin picking — because, of course, you want your Instagram Connecticut pictures to look super cute with pumpkins and gourds in them!

Visit an Authentic Apple Cider Mill

This morning, you will head from Mystic/Stonington to B.F. Clyde’s Cider Mill to get your hands on some delicious cider and mouth-watering apple cider donuts. This place is super popular in the fall, so make this your first stop of the day.

B.F. Clyde’s Cider Mill is a family-owned business that has been operating since 1881. It opens its doors on September 1 of each year and stays open until late November, seven days a week. The mill is open at 9 AM, which gives you the perfect opportunity to get an early start on the day.

Clyde’s offers both sweet and hard ciders, so there’s something for everyone. While you are there, enjoy the cider-making demonstrations, the wine and hard cider tastings at their mill store, and the adorable gift shop.

You can buy so many apple goodies in their store that you may have difficulty deciding what to get.

Whatever you do, don’t miss out on Clyde’s delicious apple cider donuts. They’re among my favorites!

Ride a Steam Train

After leaving the Cider Mill, head toward the charming town of Essex.

This small town has a stunningly beautiful downtown area that’s filled with historic homes and shops along Main Street. There are many unique stores selling everything from clothing to souvenirs.

It’s also home to the Essex Steam Train and the historic Griswold Inn and Restaurant, which makes for a fabulous stop for lunch.

Go Apple Picking and Get Lost in a Corn Maze

For the day’s last stop, hop back in the car and head to Lyman Orchards for apple picking and a one-of-a-kind corn maze. These two fall activities in Connecticut will be fun for the whole family.

You will not find a better experience than Lyman Orchards. This family-run farm has been in operation since 1741. Visit the pick-your-own orchard, which has many varieties of fruits.

Stop off at the Apple Barrel Farm Market & Bakery for homemade ice cream and delicious apple pie. Finally, end your day with a trip through the giant corn maze.

I guarantee it will be a day you will not forget.

For tonight’s stay, head to the Inn at Middletown.

The Inn at Middletown is a 100-room boutique hotel on Main Street.

It was once the National Guard Armory, and now it’s a home for travelers looking for a comfortable, clean place to stay.

The hotel offers an indoor heated pool, free high-speed internet, and plenty of parking.

It’s within walking distance from restaurants and other amenities in town.

This is the spot if you’re looking for a place to rest your head after a long day of sightseeing.

Day 3 – Yale University and Litchfield Hills

Today, you will begin the day in New Haven exploring Yale University, which has existed since 1701. You will end the day in the beautiful Litchfield Hills area.

Litchfield Hills is a beautiful area of Connecticut full of hiking trails, scenic parks, and quiet towns. The area is known for its charming small towns, picturesque drives, and delicious food. In fact, there are so many fun things to do in Litchfield Hills that you may not know where to start.

Explore the Yale Campus

Although not necessarily a fall activity, you should make a stop at Yale University in New Haven.

Yale University campus is open to the public, and you can take a one-hour student-guided tour or explore it independently.

If you have kids 6-11, ask about the Kids’ Architectural Treasure Hunt. It’s a way they can participate in a fun way while on a campus tour.

I recommend taking a tour to learn about Yale’s history and architecture.

There are many notable spots on campus, but the art gallery and library are two standouts for sure.

The Yale University Art Gallery is free and open to the public. It’s the oldest university art museum in America.

Sterling Memorial Library is another must-see spot on campus. It’s an incredible example of Gothic Revival architecture, with stunning stained glass windows and a rich history.

Dedicate at least two hours of your time to seeing the entire campus.

Visit a Pumpkin Patch

After visiting Yale, head for the car. You are heading to a pumpkin patch!

One of the best fall activities in Connecticut is going to a pumpkin patch. Enjoy pumpkin picking and a hayride this afternoon at Jones Family Farm in Cromwell, CT.

They’ve over 50 acres of pumpkins, including white pumpkins, Cinderella pumpkins, and even blue pumpkins. They also have a variety of squash and gourds to choose from.

I visited from Texas and really couldn’t take a pumpkin home with me, but walking through the patch and taking pictures is fun.

After visiting the pumpkin patch, buy an authentic farm hayride ticket. The tractor-pulled wagon takes you through the beautiful property as you enjoy views of the rolling hills and beautiful trees.

The perfect end to your day is a stop at the wine-tasting room, where you can try some local wines while enjoying snacks from their farm store.

You will find a visit to this pumpkin patch makes the perfect family-friendly fall day trip or weekend getaway.

Stay at The Litchfield Inn

For tonight’s accommodations, check into The Litchfield Inn.

The Litchfield Inn, located in the foothills of the Berkshires in Connecticut, is a colonial boutique hotel with thirty-two guest rooms.

As you enter the property, you are greeted with a grand white colonial building that oozes charm. The entry welcomes you with a circular drive leading to the check-in area. Complimentary snacks and drinks are immediately offered as you check-in.

The welcoming lounge spaces next to crackling fireplaces remind me of a cozy cottage, but those pale in comparison to the relaxing outdoor spaces.

The property backs up to hundreds of acres of conservation land, and its ten acres of serene landscape and relaxing common areas offer guests a true getaway from the hustle and bustle of everyday life.

The backyard has stone patios, flower-lined pathways, and outdoor firepits that create the perfect ambiance for winding down from your day.

Day 4 – Enjoy Fall Activities in Connecticut

After a delicious breakfast, pack up and head out for some fresh air.

Go Hiking and Explore the Thoreau Footbridge

There is no better way to enjoy fall in Connecticut than being outside, enjoying cooler weather, and being amidst the fall leaves changing colors.

Connecticut is the perfect home to many well-marked and scenic hiking trails like those found at The Hidden Valley Preserve.

The Hidden Valley Preserve Nature Center in Washington Depot is free to visit and makes the perfect place to hike or enjoy a picnic. With 650 acres of trails and plenty of spots to explore, you can spend hours getting lost in the woods without ever feeling too far from civilization.

Some of the most popular highlights of this preserve include the Thoreau swaying footbridge that crosses over the Shepaug River. One really cool feature of the suspension bridge lies on its handrails, where quotes from 19th-century philosopher Henry David Thoreau’s writings are etched.

For a true adventure, head along the trail to find the abandoned quartz mine which you can explore.

Make a Gilmore Girls-Inspired Stop

After your morning hike, take a break and visit the Mayflower Inn & Spa; the inn is said to have inspired the cult favorite Gilmore Girls hit TV show.

After visiting, it is easy to see why The Mayflower Inn is considered one of Connecticut’s most beautiful and romantic places to stay.

The Mayflower Inn & Spa is an elegant country estate with fifty-eight acres of beautifully landscaped gardens and grounds with meandering paths. There are several places to sit and enjoy your surroundings, with firepits and patios overlooking the countryside.

Many leisure activities are available during your stay here, including bird watching, biking, gardening, cooking classes, fly fishing, hiking, and more.

A stay here is more of a retreat at an English country house than a quick overnight stay, which comes at a price.

The good news, though, is you don’t have to stay here to enjoy lunch in The Garden Room or cocktails at The Tap Room, both with menus created by a James Beard award-winning chef.

The staff is gracious enough to let you roam the grounds, visit the library, and stop by the spa, even if you are not guests.

Take a Scenic Drive

After exploring the Mayflower Inn & Spa and enjoying a leisurely lunch, spend your last afternoon taking one of the most scenic drives in Connecticut.

Route 7 is a popular road for cyclists and motorcyclists, but it’s also known as “The Litchfield Hills Scenic Byway.”

The road runs through the Litchfield Hills region of Connecticut, which is home to beautiful fall foliage. You can drive Route 7 in either direction and see some amazing views along the way.

There are many beautiful towns to explore in this area, including Kent, Salisbury, and New Milford.

As you drive through the area, keep an eye out for cute roadside attractions, like this giant cow and antique truck. You might also find surprising stops, like the White Flower Farm and the Arethusa Farm and Dairy, for the most amazing ice cream.

New Milford is the last stop for day four of your fall Connecticut itinerary.

Fans of the beloved TV show Gilmore Girls may know this charming town is believed to have inspired the show’s fictional Stars Hollow.

Its picturesque common area known as the town green, quaint shops, and friendly community vibe make it a lovely town to spend the afternoon.

Strolling through New Milford’s idyllic streets, fans can immerse themselves in a setting reminiscent of Lorelai and Rory’s adventures, complete with cozy cafes and charming boutiques, making it a must-visit for enthusiasts of the series.

Say Good-bye to Connecticut

The fall season brings with it a wide range of activities to enjoy in Connecticut. Visit a cider mill, take a trip on a steam train, go apple picking and get lost in a corn maze. Whatever you choose, make sure to go out and explore Connecticut.

Whether your interest is history, nature, or good old-fashioned fun, I hope this 4-day itinerary filled with fall activities in Connecticut helps you plan your trip.

If you’re looking for more things to do, why not check out our other posts about New England in the fall? I’ve got plenty of ideas for you!

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