Things to Do in CT in September: Top Ways to Fall into Fun

As a typical New Englander, I’m a huge fan of the fall.

The foliage, the harvests, the festivals, you name it.

And while October gets all the fall glory, September has benefits as the transitional month between summer and autumn.

September is still warm but rarely as hot as August and July.

So, it’s still pool weather. We don’t close our outdoor pool until the beginning of October, usually. And while it may start getting a bit chilly, it’s still delightful to lounge beside it with a good book.

And yet, that slight drop in temperature keeps you from breaking a sweat when you’re out for a walk.

Among the many fall and summer things to do in CT in September.

Read on for the full list.

Fun events across CT in September

September is when fall festivals kick off.

From Labor Day weekend on, the weekends in September are always busy with shindigs and the like.

Celebrating the annual harvest season (back when year-round avocados and bananas, among other produce, weren’t a thing), you’ll find:

Food trucks
Farm animals
Live entertainment, including live music
Arts and crafts for sale
Antiques, from cars to furniture
And classic carnival rides and food

A few top fall festivals across Connecticut that happen in September include:

The Connecticut Renaissance Faire
The Norwalk Oyster Festival to celebrate the second most famous New England seafood
Jazz Fest in White Plains, NY
The Cider Saturday and Harvest Celebration at the New Canaan Nature Center
The annual Pumpkin Festival in Seymour
Saint Peter’s Annual Apple Festival in Monroe
Octoberfest in Peekskill, NY
Mystic Seaport’s Annual Antique Vehicle Show
Newtown Art Festival
Kent Fall Festival
The Guilford Fair
The Orange Country Fair
Berlin Fair (that’s Berlin, Connecticut, obviously)
The Durham Fair

Farm activities across Connecticut in September

If crowds and funnel cake aren’t your thing, you could also head to any number of farms across Connecticut.

Connecticut wineries on the CT wine trail are great places to enjoy the early fall weather with a glass of wine. And yes, Connecticut does have a wine country.

You can also enjoy an outdoor patio at one Connecticut’s many local breweries to enjoy the harvest of a different crop.

Or head to farms across Connecticut for some of the typical autumn activities, like: apple picking, perusing pumpkin patches, or getting lost in corn mazes.

A few of the top farms in Connecticut include:

Lyman Orchards in Middlefield
Silverman’s Farm in Easton
Jones Family Farms in Shelton
Bishop’s Orchards in Guilford

Many of these also have cider mills up and running for the fall season.

Top Day Trips for enjoying fun things to do in CT in September

Or plan Connecticut day trips in September around the many things to do across the state. Each corner of Connecticut hosts charming little towns, so lump a few together to make a busy day or long weekend.

And with the kids back in school, a weekday in September is perfect for seeing those attractions that are swamped during the summer months.

A few of the most popular destinations across the Nutmeg State for September include:

September day trips along Connecticut’s Gold Coast

Stretching from Greenwich to as far as Stratford (depending on whom you ask), the Gold Coast of Connecticut is surprisingly diverse.

End of the summer beach day trips

September is still beach weather. The water may be too cold for you, but the sand is still warm and loungeable.

Some of the best beaches along the Gold Coast for your next beach day are:

The most unique attractions on the Gold Coast of Connecticut

Most equate Fairfield County with wealth and preppiness.

And much of the area doesn’t disappoint. And a trip to explore the shopping on Greenwich Avenue or a Sunday Greenwich Polo match will provide that ambience.

But it also has a long history of attracting creative types. Being so close to a global creative capital helps.

Without question, the most unique and historic sites in this corner of Connecticut are:

The Philip Johnson Glass House in New Canaan
The Sheffield Island Lighthouse off the coast of Norwalk
The PT Barnum Museum in Bridgeport
The Weir Farm National Historic Site in Wilton
The Lockwood-Mathews Mansion Museum in Norwalk

Connecticut Gold Coast Museums

A few of the top Connecticut museums to visit here during the month of September include:

Greenwich Historical Society
The Bruce Museum in Greenwich
The New Canaan Nature Center
The Stamford Museum and Nature Center
The Aldrich Museum of Contemporary Art in Ridgefield
The Maritime Aquarium in Norwalk

Day trips around Mystic, CT in September

I consider Mystic, Connecticut the Myrtle Beach of New England. Not because it’s tacky, but it is a major tourist destination for the area.

And considering September has the warmth of the summer without the crowds, this is a better time to visit, in my opinion.

Grab a slice of pizza at Mystic Pizza, the business that was lucky enough to have the name now equated with a Julia Roberts film.

Or visit Mystic’s answer to the Maritime Aquarium. The Mystic Aquarium is a smaller institution than the one in Norwalk, but it has admittedly cooler animals. Case in point: beluga whales and penguins.

A few more of the most unique attractions near Mystic to add to your September itinerary include:

The Mashantucket Pequot Museum & Research Center in Ledyard
Mystic Seaport
The USS Nautilus at the Submarine Force Museum in Groton

Connecticut & Thames River Valleys

One of, if not the only, undeveloped river mouth in the world, the Connecticut River is a fantastic place to visit anytime of year.

It’s not called one of “the last great places on Earth” for nothing.

And two of the best ways to experience the great outdoors here are via two of Connecticut’s most unique attractions.

The Essex steam train and riverboat will take you along stretches of the Connecticut River Valley. It’s the easiest way to see the diverse wildlife that call these riverbanks home.

And Gillette Castle State Park provides a fantastic view of the river from its scenic spot on a hill. The home of an eccentric nineteenth century actor and celebrity, the castle itself is worth a peak inside, too.

Need a hint on who Gillette was?

He was the most famous actor to play Sherlock Holmes, giving him more than a few of the catchphrases we know the character for today.

Some of the charming towns to explore here include: Old Lyme, Essex, and Chester.

The Thames River, meanwhile, is more celebrated for the art and architecture you’ll find along its course.

Not as much as the original Thames, of course, but you get the idea.

Some of the prettiest CT state parks are on or close to the Thames River, such as Bluff Point

State Park and Harkness Memorial State Park.

And New London hosts a few fantastic Connecticut museums, especially the Lyman Allyn Art Museum.

New Haven

The New Haven, Connecticut area is equated with all things academia and globe-trotting. Indiana Jones would feel right at home teaching here.

And he did, sort of, as a few academic scenes of the Crystal Skull entry to the franchise were shot on the Yale campus.

Yale museums are always worth a browse, regardless of the time of year. Some personal favorites for self-guided tours are the Yale University Art Gallery, the Museum of British Art, the Peabody Museum of Natural History, and the Beinecke Rare Book and Manuscript Library.

New Haven is also home to the world’s largest indoor ropes course. It and the museums make New Haven a safe place to go for indoor activities on the rare days the weather’s crummy.

But get outside of the city to experience some more unique things to do in Connecticut in September.

A trolley line used to stretch from New York City to Boston. Buses replaced this more quaint way to travel, though the memory lives on at the Shore Line Trolley Museum in East Haven.

Madison hosts the longest stretch of any of the Connecticut beaches. The two mile long stretch of sand along Long Island Sound is typically less crowded than beaches closer to Greenwich and the Gold Coast.

September is also ideal for taking a boat tour of the Thimble Islands off the coast of Guilford. And the adorable downtown of Milford would make a great excuse to enjoy a CT lobster roll where it was first invented.

Hartford

The home of the Connecticut state house, among other government buildings, Hartford is the home of Victoriana in New England.

If you feel like getting outdoors, be sure to ride the antique carousel at Bushnell Park. And the

Elizabeth Park Conservancy is always a beautiful place to be in the warmer months of the year.

And you can soak up one more summer trip to an amusement park with a visit to Lake Compounce, in nearby Southington.

A charming nearby town to explore on a nice September is Wethersfield. Historic homes from the colonial to the Victorian era line the streets of Connecticut’s largest historic district.

Museums and Historic Sites in and near Hartford

If you’re in need of air conditioning, or somewhere dry, during your visit to Hartford, there are more than a few museums and indoor attractions to explore.

Some personal favorites here include:

The Wadsworth Atheneum Museum in downtown Hartford
New Britain Museum of American Art
The Mark Twain House and Museum, where he created famous characters such as Huckleberry Finn and Tom Sawyer
And the New England Air Museum in Windsor Locks

Litchfield County

Northwest Connecticut is the place for charming small towns and sprawling state parks.

Like the river valleys further east, the Litchfield Hills are perfect for a sunny autumn day trip.

Added benefit is this area inspired the creators of the Gilmore Girls.

Head up on a Sunday to visit Elephant’s Trunk flea market. The largest flea market in New England is also the coolest of the flea markets in Connecticut.

Then, head further north into Litchfield County for small towns along Route 7 like Kent and Sharon. Or head closer to the Hartford area for Litchfield and Simsbury.

Be sure to include a few Connecticut state parks on your trip. Some favorites include Kent Falls State Park and Lake Waramaug.