Things To Do In CT In September: Top 23 Most Unique Spots | Stanton House Inn
the gardens at harkness memorial state park, one of the best things to do in CT in September

Things to Do in CT in September: Top 23 Most Unique Spots

outdoor pool on an early fall dayAs 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

cider mill, one of the best things to do in CT in SeptemberIf 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




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 summer road trips in September include:

September day trips along Connecticut’s Gold Coast

sherwood island, one of the most fun things to do in CT in SeptemberStretching from Greenwich to as far as Stratford, CT, (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

Greenwich HarborMost 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:

Connecticut Gold Coast Museums

woods in Stamford, ConnecticutA few of the best museums in Greenwich, CT, and museums in the rest of Fairfield County to visit here during the month of September include:




  • The New Canaan Nature Center




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:

Connecticut & Thames River Valleys

A visit to the shore of the Connecticut River is one of the best things to do in CT in SeptemberOne 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?


historic home in EssexHe 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:




  • And Chester, Connecticut


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

Yale university campusThe 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.


historic homes in New Haven, one of the best things to do in CT in SeptemberA 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, CT, would make a great excuse to enjoy a CT lobster roll where it was first invented.


The home of the Connecticut state house, among other government buildings, this is Connecticut’s capital city, after all. The city of Hartford, CT, 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, Connecticut.


A charming nearby town to explore on a nice September is Wethersfield, Connecticut. 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:

Litchfield County

Flower bridge in SimsburyNorthwest 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.

Keeping exploring the most unique things to do in CT in September (and the fall)

another cute historic home in Essex, ConnecticutAny time of year is an ideal time to explore Connecticut.


But Connecticut in the fall is the most stereotypical time of year for visitors. So why not play along?


Some more CT fall activities to add to your visit plan include:

Be sure to read our guided tour to each month of the season, aside from September:


And don’t forget to read the full guide to the best attractions, activities, and things to do in Connecticut in the fall.

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