The Ultimate Connecticut Road Trip: The Best Places to Visit in the Fall
The first time my sisters and I did a New England road trip, we crammed as much as possible into five days. It was amazing, but when we got home, we knew we had to go back. This time, we focused on one state: a Connecticut road trip. And since we’re longtime Gilmore Girls fans, we used the show as our guide.
This road trip is for you if you’ve ever wanted to step into Stars Hollow while soaking up peak fall vibes.
Connecticut in the fall is everything Texas isn’t—crisp air, fiery leaves, pumpkin patches, and apple cider so fresh you’ll want to move here.
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.
He Works So I Travel content may contain affiliate links for products I use and love. If you make a purchase after clicking one of these links, I’ll earn a small commission at no additional cost to you. For full details, please read my full affiliate disclosure here.
Travel Resources for Connecticut
- Score the cheapest flights to Connecticut using Skyscanner.com
- Compare rental car prices in New England using Discovercars.com
- Book your Connecticut accommodations with Booking.com
Day 1: Flying In & Falling for Mystic
We started our Connecticut road trip by flying into Providence, Rhode Island.
Why? It’s an easy airport, car rentals are simple, and it’s a short drive to Connecticut.
We picked up our rental car and made the one-hour drive to Mystic, a perfect first stop.
Mystic is the kind of town that makes you want to slow down, grab a coffee, and wander.
We checked into The Whaler’s Inn, a charming boutique hotel in the heart of town. Then, we did all the Mystic musts:
- Shopped at the cute local boutiques – I may or may not have bought a Gilmore-esque knit sweater.
- Sipped wine at Johnathan Edwards Winery – Because what’s a girls’ trip without wine?
- Ate at Mystic Pizza – Yes, the same one from the 1988 movie. Cheesy? (Both literally and figuratively.) Absolutely. Worth it? 100%.
- Watched the drawbridge in downtown Mystic – It’s oddly mesmerizing.
Where to Stay in Mystic/Stonington
- Whaler’s Inn—This charming inn is 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. Everything you could want is included in this rental, right down to the bottle of water and chocolates left next to your bed.
Day 2: Cider Mills, Corn Mazes & Essex
We began the day with breakfast at the Shipwright’s Daughter, a casual but upscale restaurant in Mystic. Connecticut’s Restaurant Association recently named it Restaurant of the Year. It was the perfect send-off for day two.
Today’s itinerary is packed!
Visit an Authentic Apple Cider Mill
If fall had a scent, it would be whatever magic is in the air at B.F. Clyde’s Cider Mill, the first stop of the day.
B.F. Clyde’s Cider Mill is an institution, a family-owned business that has been operating since 1881.
It opens on September 1 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 sweet and hard ciders, so there’s something for everyone. While you’re there, enjoy the cider-making demonstrations, 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!
Next up on our Connecticut road trip? Fall activities.
Ride a Steam Train
After leaving the Cider Mill, we visited the charming town of Essex, one of the most picturesque small towns in Connecticut.
Think historic homes, tree-lined streets, and a waterfront straight out of a postcard.
Essex is also home to the Essex Steam Train, a vintage train ride that’s peak New England in the fall.
You’ll want to visit the historic Griswold Inn and Restaurant in Essex for a fabulous lunch stop.
Go Apple Picking and Get Lost in a Corn Maze
Texas doesn’t exactly do crisp autumn air and golden leaves, so we were all in for a proper corn maze and apple-picking experience.
There are many options for fall activities on a Connecticut road trip, but we found a great one at the corn maze at Lyman Orchards, a family-run farm that has operated since 1741.
If you’ve ever wanted to wander through rows of towering cornstalks, getting hilariously lost while trying to find the exit, this is the place.
Before leaving, stop at the Apple Barrel Farm & Bakery for homemade ice cream and delicious apple pie.
I guarantee it will be a day you will not forget.
Where to Stay on Day Two of Your Connecticut Road Trip
For tonight’s stay, head to the Inn at Middletown.
The Inn at Middletown is a 100-room boutique hotel on Main Street in Middletown, CT.
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
Explore the Yale Campus
We kicked off the morning by visiting Yale University in New Haven. The campus is stunning, especially in the fall, when the ivy-covered buildings feel extra cinematic. Rory Gilmore would approve.
Yale University campus is open to the public, and you can take a one-hour student-guided tour or explore it independently.
There are many notable spots on campus, but the art gallery and library are two standouts.
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
From Yale, we drove to Litchfield Hills, where Connecticut turns into a Hallmark movie.
Rolling hills, white steeple churches, and winding roads lined with fall foliage—it’s all here.
We spent the afternoon enjoying some of the best fall activities in Connecticut by picking pumpkins at Jones Family Farm, browsing the farm store, and debating whether we could fit a hay bale in our rental car. (We couldn’t.)
With over 50 acres of pumpkins, including white pumpkins, Cinderella pumpkins, and even blue pumpkins, we enjoyed taking pictures, going on a hayride, and loving the farm.
The tractor-pulled hayride was a highlight, taking us through the beautiful property as wee enjoyed 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
We checked into The Litchfield Inn, a cozy spot perfect for unwinding after a full day of fall fun.
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.
The Litchfield Inn is located in Litchfield, a quaint historic town with unique shops and restaurants.
Named one of the Top 15 Small Towns in the USA by The Smithsonian Magazine, you will love spending your evening here.
Complimentary amenities such as parking and a full complimentary breakfast buffet make this inn a fabulous deal.
Day 4: A Stars Hollow Pilgrimage
This was the day of our Connecticut road trip that we’d been waiting for: visiting the places that inspired Gilmore Girls.
Go Hiking and Explore the Thoreau Footbridge
There is no better way to enjoy fall in Connecticut than being outside, enjoying cooler weather, and observing the changing colors of the leaves.
First stop: The Hidden Valley Preserve in Washington Depot. This quiet hiking spot feels straight out of the show, perfect for pretending you’re on a stroll with Lorelai.
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 our morning hike, we took a break and visited the Mayflower Inn & Spa.
This dreamy hotel is said to have inspired the Gilmore Girls hit TV show Independence Inn. We didn’t stay here (because budget), but we did stop in for coffee and to soak in the ambiance.
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.
During your stay, you can engage in many leisure activities, 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, we took a we took a scenic drive along Litchfield Hills Scenic Byway, which was, as expected, stunning.
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, home to beautiful fall foliage. You can drive Route 7 in either direction and see some amazing views along the way.
This area has many beautiful towns to explore, including Kent, Salisbury, and New Milford.
As you drive through the area, look 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 fantastic ice cream.
New Milford, Connecticut
Finally, we made it to New Milford, the town that most people believe inspired the show’s fictional setting, Stars Hollow.
The town green, the gazebo, the charming shops—it all has that Gilmore-esque feel. We grabbed coffee, wandered downtown, and soaked up every second.
Day 5: One Last Drive & Heading Home
We squeezed in one more scenic drive on our last morning before heading back to Providence to catch our flight. Connecticut, you were perfect.
The Best Time for a Connecticut Road Trip
The short answer to the question of the best time to visit Connecticut is fall!
Connecticut is a wonderful place to visit in the fall. From the colors of the leaves and the crisp, cool air to the fun festivals and events throughout the state, there’s a lot to love about autumn in Connecticut.
As you plan your Connecticut road 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, 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.
Sample 5-Day Connecticut Fall Itinerary
- Day 1: Arrive in Providence, RI. Drive to Mystic. Explore Mystic.
- Day 2: Visit B.F. Clyde’s Cider Mill, corn maze, Essex, pumpkin picking.
- Day 3: Yale, Litchfield Hills, Jones Family Farm.
- Day 4: Hidden Valley Preserve, Mayflower Inn, Litchfield Hills drive, New Milford.
- Day 5: Scenic drive, return to Providence, fly home.
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 5-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!
