Little, overlooked Connecticut is a state of many firsts.
For example, Connecticut was the first state to institute speed limits to drivers. It did so in 1901, and declared that going over 12 miles per hour was speeding.
If Connecticut had kept that law in place, perhaps it wouldn’t be seen as just a drive-through state for travelers between New York and Boston.
Or maybe those travelers would just malign Connecticut more than they do now.
But if they stopped and had a look around, maybe they’d understand better why locals love Connecticut so much.
Especially during fall in CT.
Granted, travelers can still enjoy the visual splendor of Connecticut fall foliage from the highways. But there’s so much more to experience when it comes to fall in Connecticut.
Read on for our guide to getting the full experience of fall in Connecticut.
Your Bucket List of Things to do in Connecticut in the Fall
Maybe it’s shows on TV, or movies, but people seem to most often equate Connecticut with autumn.
And for good reason, it, like many other New England states, truly shines during those few months between summer and winter.
Sometimes, it’s helpful to have a list in front of you to keep track of all that there is to see and do. Hence the original source of this article.
Connecticut fall foliage
Of all the New England states, Connecticut boasts the longest season for fall foliage.
While every year is different, Connecticut fall foliage is most vibrant from early October to very early November. The Connecticut Forestry Department and others refer to that period as “peak foliage”.
Peak foliage hit CT in 2019 in this period. Some years we get to enjoy the foliage well into early November, but that’s an anomaly.
Connecticut fall foliage driving routes
Driving along scenic roads is the most obvious pick for seeing CT’s fall foliage for yourself.
While the speed limits are much higher than they were in 1901, don’t go too fast, or you might miss the best parts.
Some of the top picks for Connecticut fall foliage driving routes include:
Driving from Greenwich into the Litchfield Hills
Round Hill Road, North Street, and Lake Avenue in Greenwich, CT
The Shoreline drive to Essex, CT
That last option, of driving to the stretch of CT shoreline towns from Guilford to Essex, is a longer trek.
Essex, CT, fall foliage
But it’s worth the trip, as this fall foliage destination offers one of the most unique Connecticut experiences in the state.
That is, if you can get tickets for it.
The Essex Steam Train leaves from the historic Essex, CT, train station. From there, it pulls its vintage coaches along the Connecticut River Valley on a 12-mile round trip stretch of old train track.
If an old-fashioned riverboat is more your thing, the Becky Thatcher riverboat leaves from Deep River’s landing for an hour and a half journey.
While both of these attractions run throughout the year, fall foliage season is among the most spectacular times to take a ride.
Connecticut fall foliage day trips
Speaking of the Essex Steam Train, there is more to experiencing the fall than simply driving around.
The third smallest state in the Union, no town in Connecticut is far from anywhere else in the state.
The longest drive, along the Connecticut shoreline, takes less than 2 hours.
But I encourage you to take way longer than that, so you can stop and explore some of the best fall towns on your Connecticut day trips.
Best Connecticut towns in the Fall
Pretty much any town in Connecticut has something appealing about it in the Autumn.
But Connecticut has 169 towns, so we all have to prioritize.
You may be surprised to learn that this Greenwich native is not including Greenwich on the list of Connecticut towns to visit.
Greenwich is beautiful any time of year, and there are plenty of things to do year-round. That said, the towns on this list are built around the Fall.
And all of them, Greenwich included, made our list of the best cute towns in Connecticut.
Connecticut’s number one tourist attraction is a prime destination for visitors looking to experience the Fall.
Mystic Seaport looks straight out of a magazine in the fall, with historic buildings draped in fall color. And the blue of Mystic harbor’s water is a perfect contrast to the explosion of color on the surrounding shores.
Visit the local farms for fall goodies, and check-out B.F. Clyde’s steam-powered cider mill. It’s the last one in America, and was designated a National Mechanical Engineering Landmark in 1994. Even if you’re not into historic mechanical marvels, the cider slushies and cider donuts are delicious.
Litchfield County Hill Towns
There are a lot of towns in this part of the state.
They’re all so small, though, that an afternoon would be enough to knock most of them off your list without too much of a struggle.
- Cornwall features one of the historic covered bridges that screams New England in the fall.
- Kent has Kent Falls State Park, Bulls Bridge, and an artsy community that’s become a big draw for New Yorkers with cars.
- New Milford has the cutest town green and quaint downtown. I’d be shocked if it hasn’t been featured in movies.
Activities for Fall in CT
Sure, walking around the downtown of a cute Connecticut fall town can be fun, but what about things to do?
If you’re the type that wants to do a quick photo shoot, pumpkin in hand, for Instagram; or more interested in disconnecting and getting lost in the fall woods, Connecticut in the fall has you covered.
Be sure to read our full guide to fall activities in CT, but for a primer:
Fall foliage hikes
Pretty much anywhere in the state has fantastic hiking trails to see fall foliage.
Of all the Connecticut hiking trails, though, one of the more intense hikes rewards with one of the most splendid fall views in Connecticut.
Heublein Tower, perched on a ridge in Talcott Mountain State Park, requires a steep hike. But once you get there, the tower offers a 360 degree view of the surrounding area. Hartford and the surrounding towns are within sight, plus the surrounding hills and valleys, swathed in golds, reds, and oranges.
Farm visits during Fall in CT
While downtown Greenwich and Stamford hide this fact well, the area and Connecticut only recently made the switch from rural to suburban. Like much of the country, Greenwich made the switch only in the last few decades.
And there are large stretches of the state that are still magically rural. And the farms that still work here are prime places to visit in the fall.
September and October are perfect months to go apple picking in the various Connecticut apple orchards, for example.
Many farms stretch the season-out by offering pumpkin picking and corn mazes, too.
There’s a reason people associate Connecticut with hauntings. It’s one of the oldest states in the Union, with plenty of opportunities to acquire a spirit or two with unfinished business.
While many of the most haunted houses are privately owned, there are still some fun haunted houses for Halloween. Try to snap a picture of the ghosts at the Lockwood-Mathews Mansion museum. Or head to Mill Hill Historic Park for a lantern-lit walk through the graveyard.
A haunted house can be a fun way to give yourself a little scare.
Find a Haunted Place in Connecticut
If you’d rather something a little less structured, you can check-out some of the most haunted places in Connecticut:
- Bruce Museum in Greenwich
- Union Cemetery in Easton
- Dudley Town (careful, this is private property)
Explore the Stomping Grounds of the Headless Horseman
I admit this isn’t in Connecticut, but nearby Tarrytown and Sleepy Hollow are the site of one of the most famous American short stories.
And these two Hudson River Valley towns cash-in each year on their most famous undead resident with all sorts of Halloween events.
Fall Festivals in Connecticut
While Sleepy Hollow’s events are well known, there are plenty more fall festivals in our state. Click the link to see our full list of fall festivals and events in Connecticut.
Fall Beer and Wine Tastings
If you’re not all farmed-out from pumpkin and apple picking or exploring corn mazes, there are still more farms to check-out.
In this case, Connecticut has a growing vineyard and winery industry scattered throughout the state. Read our guide to the best wineries on the CT wine trail for a full trip.
I’m personally more partial to the beer brewed in Connecticut than the wine. But to each their own.
We’ve got a list of the best breweries in Connecticut and Westchester County, if an autumnal day of sampling local brews is more your style.
Fall Antiquing in Connecticut
The Greenwich Avenue shopping district is always a top destination.
But fall just seems like the perfect time to go antiquing through New England for some reason.
Comb through the Connecticut Antiques Trail’s list of antique shops and pick a few along your planned day trip route. I also highly recommend the Elephant’s Trunk flea market in New Milford on a Sunday morning in the fall.
November in Connecticut
Most visitors to Connecticut will recommend you experience the above activities in September and October.
But the fact that everyone does these things then means that other months have their own pleasures.
In the case of November in Connecticut, fall foliage extends into the beginning of the month. And with fewer people, you often have entire attractions to yourself.
What about Connecticut in the winter?
Yes, fall is synonymous with New England and Connecticut.
But winter in Connecticut has its own special features that you can only appreciate when you’re here.
There are plenty of romantic things to do in CT during the winter months.
Be sure to check-out our guides to:
- Winter activities in Connecticut
- The best places to visit in Connecticut for winter vacation getaways
- The best things to do in Connecticut in December
Click over to our guide on planning a romantic winter weekend getaway in Greenwich, CT, if you’d like the planning done for you.
Keep Planning Your Fall in CT Getaway
Still not convinced that you have to experience fall in CT?