Little, overlooked Connecticut is a state of many firsts.
Connecticut was the first state to institute speed limits for drivers. It did so in 1901, declaring that going over 12 miles per hour was speeding.
If Connecticut had kept that law in place, perhaps it would not 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.
Granted, travelers can still enjoy the visual splendor of Connecticut fall foliage from the highways. Still, there’s so much more to experience when it comes to fall in Connecticut.
Read on for our guide to getting the full fall experience in Connecticut.
Your Bucket List of Things to do in Connecticut in the Fall
Maybe it’s the shows on TV or movies on the big screen, including:
- “Gilmore Girls”
- And “the Haunting in Connecticut”
But people seem to most often equate Connecticut with autumn.
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. So without further ado, here are some things to keep an eye out for in Connecticut this fall.
Connecticut Fall Foliage
Connecticut boasts the longest season for fall foliage in all New England states.
While every year is different, Connecticut’s fall foliage is most vibrant from early October to very early November. The Connecticut Forestry Department and state foresters refer to that period as “peak foliage” in their foliage report. Some years, we can enjoy the foliage well into November, but that’s an anomaly.
Connecticut Fall Foliage Drives
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 in 1901, don’t go too fast, or you might miss the best parts of leaf peeping.
Some of the top picks for Connecticut fall foliage scenic driving routes include points from each of the corners of the state:
- Merritt Parkway
- Driving from Greenwich into the Litchfield Hills
- Route 136
- Round Hill Road, North Street, and Lake Avenue in Greenwich, CT
- The Shoreline drive to Essex, CT
Essex, CT, Fall Foliage
That last option for scenic driving, to the stretch of CT shoreline towns from Guilford to Essex, is a longer trek. However, it’s worth the trip, as this fall foliage destination offers one of the most unique Connecticut experiences in the state.
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. It then takes you for an hour-and-a-half journey along the fall colors of the Connecticut River Valley.
While 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.
Still, 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.
Nevertheless, 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.
Moreover, 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.
Many of the best attractions, activities, and things to do in Mystic, Connecticut, are best enjoyed in the fall.
Mystic Seaport looks straight out of a magazine in the fall, with historic buildings draped in fall color. The blue of Mystic harbor’s water perfectly contrasts 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 many 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 struggle.
But if you’d rather spend more of the day in any given town, head to one of the many nearby CT state parks.
- 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 complete guide to fall activities in CT, but here are some ideas as a primer:
Fall Foliage Hikes
Almost anywhere in the state has fantastic hiking trails through parks and forests to see fall foliage.
Of all the Connecticut hiking trails, though, one of the rewards of the more intense hike, 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 Farmington River Valley. Hartford and the surrounding towns are within sight, plus the surrounding hills and valleys, swathed in golds, reds, and oranges.
Mohawk State Forest, straddling Goshen, Cornwall, and Litchfield, offers plenty of views over its rolling hills, as well. And Pachaug State Forest, at the other extreme of the state, offers 27,000 acres-worth of opportunities to get lost in peak fall foliage.
Farm Visits During Fall in CT
Connecticut only recently switched from rural to suburban, a fact downtown Greenwich and Stamford hide well. Like much of the country, Greenwich made the switch only in the last few decades.
Still, large stretches of the state that magically rural, with farms that work here being 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 also stretch the season-out by offering pumpkin picking and Connecticut corn mazes.
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. You can also 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 sites of one of the most famous American short stories.
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, plenty more fall festivals are in our state. Click the link to see our complete 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.
To top it off, 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 stores in CT 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.
In this writer’s opinion, fall is the best time to explore the top Connecticut flea markets.
November in Connecticut
Most Connecticut visitors recommend you experience the above activities in September and October.
However, the fact that everyone does these things 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?
Fall is synonymous with New England and Connecticut. And yet, 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
Read up on our guide to 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
Are you still not convinced that you have to experience fall in CT?
Updated and republished: September 19, 2022