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Thinking about visiting Connecticut in the fall and wondering what it’s like? Is it worth visiting when New England has so many other incredible highlights?
After my third fall living in CT, I’m here to unequivocally say: Connecticut is underrated. (And yes, this is coming from the one who’s head-over-heels for my home state of Maine.)
Highlights of fall in Connecticut include: charming small towns, beautiful weather, scenic back roads, and a lot of variety within driving distance. Connecticut is especially pretty in October when its long foliage season extends throughout the state.
Because it sits in the shadow of some other New England giants, it’s often overlooked, apart from a half day in Mystic as part of a whirlwind tour of all six states. I won’t claim that Connecticut’s landscape rivals the rugged, awe-inspiring beauty of Maine, New Hampshire, and Vermont.
But if you approach it with curiosity, you’ll find a lot of gems and quintessential New England fall charm in The Nutmeg State.
Keep reading for five reasons you shouldn’t overlook Connecticut during the fall, plus the type of trips I recommend.
Top Reasons to Visit Connecticut in the Fall
Foliage season is typically longer than in other New England states.
Even though Connecticut is a small state, it holds its own in the fall foliage department. The geography here helps extend the season.
And the fact that it is such a compact state means that peak foliage is probably just a day trip away in October—no matter where you are in Connecticut.
- The stunning Northwest (my favorite area!) and Northeast corners of the state are the first to peak, typically around early to mid-October.
- The middle areas of the state follow, usually in mid-October towards the end of October.
- Most of CT’s shoreline typically sees peak fall color towards the end of October and sometimes into early November (especially Fairfield County, closest to NYC).
Keep in mind that this varies from year to year. The 2023 foliage season has been a bit later than usual, and the heavy rain made for less vibrant color.
Unfortunately, Connecticut doesn’t have actual reporting of current foliage like some other states, but there are several resources that offer forecasted estimates of upcoming fall foliage:
There are impossibly cute small towns.
Read: It’s a real-life Gilmore Girls setting.
The town of Stars Hollow, CT might be technically fictional, but it was based on a real-life trip the show creator took to Litchfield County (the Northwest corner).
And I can tell you from experience: if you drive around Connecticut’s back roads long enough, I guarantee you’ll stumble across some of the cutest small towns imaginable.
And quirky town events? From a town scarecrow contest to fall festivals to a pumpkin patch train, there are always fun autumn discoveries around the state.
Whether or not you’re a Gilmore Girls fan, you’ll love Connecticut’s classic New England towns in the fall.
Experience gorgeous autumn weather.
While most locals flock to East Coast beaches in the height of summer, I highly recommend shoulder season. There are many September and October days in Connecticut when it’s warm enough to enjoy a walk on the beach or head out on a sunny hike.
As I’m writing this on a late October morning, my windows are wide open and there’s just a light chill in the air. Unseasonably (it’s almost Halloween), we’re getting 75-degree weather this weekend.
There are also plenty of chilly days too—perfect for apple picking, finding your way through a corn maze, or getting cozy by a bonfire.
That’s not to say we don’t get rain—autumn has its fair share. But even those days can be quite beautiful. There’s a different quality to the foliage on a cloudy, rainy day. As long as it’s not a downpour, the not-so-sunny days don’t have to ruin your fall adventures.
You’ve got a little of everything within driving distance.
I never really thought about this being a benefit of living in a small state, but I’ve discovered how great it is to have easy day trips anywhere in the state. And there’s so much variety in Connecticut: back roads, rural farmland, beaches, small cities, nightlife, excellent cuisine, and charming small towns.
If you’re spending a weekend or longer in Connecticut, there’s a lot you can do and see within a 1-2 hour drive.
There are surprisingly beautiful back roads.
As someone who has driven through Connecticut many times on my way to Maine—all the main roads from I-84 to I-95 to the Merritt Parkway—one of the things I was most surprised by when I moved to Connecticut is how it doesn’t actually look like that.
It’s not just factory cities and tired plazas and questionable billboards.
The scenery is night and day when you start exploring the back roads.
When friends and family come to visit, it’s my mission to take them on some side roads. I tell them that to really see Connecticut, you’ve got to get off the highways.
Those one-lane roads twisting and turning through little towns are where the beauty of this state really shines. And in October, they transform into an autumn wonderland.
Who Should Visit Connecticut in the Fall (And for How Long)?
As much as I think Connecticut is underrated, I’m also a realist. It’s not a bucket-list destination, and it’s probably not a place that someone from California is going to plan a week-long trip to.
But here are some trip ideas and who they’re best for:
Weekend Trip from Drivable Destinations
An autumn trip to CT makes a great weekend getaway for residents of NYC, Boston, and neighboring states.
If you’re within driving distance, don’t sleep on Connecticut!
Part of a (Second) New England Road Trip
Most people try to hit all six states on a New England fall road trip, and that’s a LOT to pack into one trip!
I don’t want you to miss out on all the other incredible stops in other states. But if you’re coming back for a second time around, I recommend taking CT a little slower (go beyond Mystic).
Gilmore Girls Weekend Getaway
Fall is unequivocally Gilmore Girls season! A Gilmore-themed Connecticut trip is definitely destination worthy for fans of the show.
On my recent GG weekend with a friend from PA, store owners told us that people come from all over the country in search of Stars Hollow.
In Litchfield County, you can wander town greens, take photos in the gazebo, visit quirky community events (like the town scarecrow contest in Litchfield), and get the town gossip while drinking coffee. And don’t skip out on the Yale experience (plus a pizza crawl in search of the best New Haven pizza).
Depending on how far you’re traveling to get here and your travel style, I recommend planning for anywhere from a weekend to five days.
We have so much to explore in our backyard! September and October weekends are perfect for day or overnight trips to other parts of the state. Keep an eye on the foliage report and plan your trips accordingly.