We Blinked… and Somehow It's September
I can hardly believe it's September. Both Chris and I were just commenting that neither one of us even made it to the beach or the lake this summer! We're not sure if it was our crazy schedules, the weather, or what happened — but somehow, summer just flew by.
We blinked, and it was Labor Day weekend.
And thank you to everyone who came out to see us at the Southbury Green for the Billy Joel tribute concert! We had so much fun spending the evening with friends, neighbors and so many familiar faces.
In fact, we had such a good time that it got us thinking about all the other things happening around our area this month.
The good news? September in Western Connecticut is pretty hard to beat. The days are still warm, the nights start getting a little cooler, and this is when so many of the things we love about living here really get going.
The fairs are back. The orchards are opening. There's live music, food, festivals, family events and all those little local traditions that make our towns feel like home.
So since summer somehow got away from us, Chris and I decided we're not letting September do the same thing.
We started looking around Southbury and our neighboring towns to see what was coming up, and found so much that we thought, we need to share this.
So that's exactly what we did.
What's Happening in Western Connecticut This September
Whether you're looking for something to do with the kids, a fun afternoon with friends, a date night, or just an excuse to get outside and enjoy the beginning of fall, here are some of the things that caught our eye.
September 3–5 | Woodbury Fire Department Carnival — Woodbury
A good old-fashioned hometown carnival to start the month. The Woodbury Fire Department Carnival is back at Hollow Park September 3, 4 and 5 from 6–10 PM.
There will be rides and attractions, burgers, hot dogs, French fries, fried dough and fried Oreos, plus raffle prizes. And if fireworks are your thing, Saturday night is fireworks night.
Where: Hollow Park, 43 Hollow Road, Woodbury
September 3–6 | Ember Hilltop at March Farm — Bethlehem
If you're trying to hold onto summer for just a few more days, this looks like a pretty nice way to do it.
Ember Hilltop returns to March Farm September 3–6. Reservations are available September 3, 5 and 6.
Friday, September 4 is Hilltop Concert Night, and no reservation is needed that evening. Come up, grab some food and enjoy the music.
Where: March Farm, 160 March Farm Road, Bethlehem
September 4–6 | A Weekend in the Life — New Milford
Gilmore Girls fans, this one is for you.
New Milford is hosting A Weekend in the Life, a three-day small-town fan weekend with special guests, panels and Q&As, trivia, themed activities, vendors, shopping, meet-and-greets, photos, autographs and other fan events.
Guests scheduled to appear include former Gilmore Girls actors Scott Patterson, Matt Czuchry, Sean Gunn, Yanic Truesdale, Katie Walder, Olivia Hack, Gregg Henry, Colin Egglesfield, John Cabrera, Nick Holmes and Tanc Sade.
When: September 4–6 Where: New Milford
September 5 | The Insiders: Tom Petty Tribute — Newtown
Tom Petty on a Saturday night sounds pretty good to us.
The Insiders, a Tom Petty tribute band, take the stage at Edmond Town Hall at 8 PM.
Where: Edmond Town Hall, 45 Main Street, Newtown
September 6 | Bridgewater Tractor Parade — Bridgewater
It doesn't get much more Western Connecticut than this.
The Bridgewater Tractor Parade lines up at Shallow Brook Farm at 1:30 PM, with the parade beginning at 2:30 PM.
Expect tractors, floats, side-by-sides, Gators, golf carts and bikes, followed by music, awards and BBQ. The 2026 theme is America250.
September 7 | Newtown Labor Day Parade — Newtown
A true local tradition.
The 64th Annual Newtown Labor Day Parade steps off at 10 AM and travels an approximately 1.5-mile route along Main Street.
This year's theme is "Picture Perfect Parade," and Bill Glass will serve as Grand Marshal.
September 11 | Apple Season Begins at Hidden Gem Orchard — Southbury
Here we go, Southbury. Apple season!
Hidden Gem Orchard opens for the season September 11, with pick-your-own apples Friday, Saturday and Sunday from 10 AM–5 PM.
The farm grows 38 heirloom and unique apple varieties, and there are cider donuts and hand pies every weekend, plus hay wagon rides on Saturdays and Sundays. The farm stand is open Friday through Sunday from 9 AM–5 PM.
No reservations are required, and parking is free.
Where: Hidden Gem Orchard, 2500 Purchase Brook Road, Southbury
September 11–13 | 101st Bethlehem Fair — Bethlehem
If you love a traditional Connecticut agricultural fair, the Bethlehem Fair is one of those weekends that just feels like September.
The fair celebrates its 101st year in 2026 with three days of family fun, agriculture, community traditions and a full schedule of entertainment.
There's plenty happening on the Main Stage throughout the weekend, too, so check the schedule before you go.
September 12–20 | Plein Air Litchfield — Litchfield
This one is a little different — and such a great fit for Litchfield.
During Plein Air Litchfield 2026, more than 30 nationally recognized landscape artists will paint outdoors throughout Greater Litchfield during nine days devoted to art, beauty and community.
Want to try it yourself? There's also a Community Quick Paint on Sunday, September 13, open to artists of all levels.
September 18 | Fran Lebowitz — Newtown
For something completely different, writer and cultural commentator Fran Lebowitz comes to Edmond Town Hall at 8 PM.
If you enjoy her very particular take on culture, people and modern life, this should be an interesting night.
Where: Edmond Town Hall, 45 Main Street, Newtown
September 19 | Isaac Mizrahi — Newtown
Another interesting night at Edmond Town Hall.
Designer and entertainer Isaac Mizrahi will be joined by his jazz trio for an evening of live music and conversation beginning at 8 PM.
Where: Edmond Town Hall, 45 Main Street, Newtown
September 19 | Steep Rock Annual Community Picnic — Washington Depot
This just sounds like a nice way to spend a September afternoon.
The Steep Rock Annual Community Picnic runs from 12–4 PM with food and refreshments, live music, kids' games and activities, raffles and prizes.
Where: Steep Rock Preserve, 2 Tunnel Road, Washington Depot
September 19–20 | Quassy Corn Harvest Fest — Middlebury
Quassy is getting into the fall spirit with its Corn Harvest Fest September 19–20.
There will be live music both days, festival food and rides, with meal, beverage and all-day ride packages available.
Where: Quassy Amusement Park, 2132 Middlebury Road, Middlebury
September 20 | Woodbury Fall Festival — Woodbury
Another reason to head to Hollow Park this month!
The Woodbury CT Chamber of Commerce Fall Festival runs from 11 AM–4 PM with local artisans and community vendors, food trucks, music, a kids' area and a dog/pet costume contest.
Admission is free.
Where: Hollow Park, Woodbury
September 25 | Country LIVE! — Newtown
Country fans get a turn at Edmond Town Hall with Country LIVE!, a tribute concert celebrating the music of Kenny Chesney, Shania Twain, Keith Urban and Luke Bryan.
The show begins at 7:30 PM.
Where: Edmond Town Hall, 45 Main Street, Newtown
September 26 Is Going to Be a Busy Saturday
If you're looking at your calendar and wondering which September weekend to keep open, September 26 has a lot going on — especially right here in Southbury.
Washington–Roxbury Tunnel Road Connector Hike — Roxbury
Start the morning outside with a community hike celebrating the new trail connection between Washington and Roxbury.
Meet at Roxbury Town Hall at 9 AM. The hike is approximately 3–4 miles round trip and rated easy to moderate.
Families are welcome, as are leashed dogs. Bring water, wear sturdy shoes and dress for the weather.
Where: Meet at Roxbury Town Hall, 29 North Street, Roxbury
STEM-A-PALOOZA — Southbury
Have kids who love science, technology or figuring out how things work?
STEM-A-PALOOZA takes over Pomperaug High School from 10 AM–3 PM, with hands-on activities and demonstrations covering science, technology, engineering and math.
It's free and open to all ages, and is co-sponsored by the Town of Southbury and Region 15 Schools.
Where: Pomperaug High School, Southbury
32nd Annual Apple Festival — Southbury
Another Southbury favorite is happening the very same day.
The 32nd Annual Apple Festival at South Britain Congregational Church runs from 10 AM–3 PM.
You'll find more than 30 artisans, food and refreshments, historic church tours and those famous apple pies.
Where: South Britain Congregational Church, 693 South Britain Road, Southbury
Southbury Celebration — Southbury
And you don't have to go home yet.
The Southbury Celebration runs from 4–9 PM at Southbury Training School with food, live music and family fun.
Then, at approximately 8:15 PM, fireworks!
The rain date is Sunday, September 27.
Where: Southbury Training School, 1461 South Britain Road, Southbury
Maybe Summer Flying By Isn't So Bad After All
Looking at this list, we're feeling a little better about summer getting away from us.
There really is something special about September here. We still have warm days and plenty of time outside, but you can feel the season beginning to change. The fairs and apple festivals start, the farms get busy, and our towns seem to pack their calendars with all the things that bring people together.
And that's one of the reasons we wanted to start sharing more of this.
We talk about real estate every day, of course. But when someone asks us what it's like to live in Southbury — or Woodbury, Middlebury, Newtown, Bethlehem, Washington, Roxbury, Bridgewater or elsewhere in Western Connecticut — this is part of the answer.
It's not just the house.
It's knowing where to pick apples on Saturday morning. It's the Labor Day parade you go to every year. It's a little town fair, a hike with your neighbors, live music on a Friday night, or taking the kids to see the fireworks.
It's the community around the house that makes a place home.
So if summer flew by for you too, come join us in making the most of September.
And if we missed something good, please tell us. We're always looking for the local events, traditions and hidden gems we should know about — and share.
See you around town!
Lori & Chris
Lorraine "Lori" Consiglio, REALTOR® Consiglio Homes Better Homes and Gardens Real Estate | Gaetano Marra Homes (203) 725-4464
Christine Chris Curtis Author, Editor & Marketing Strategist Western CT Real Estate
Consiglio Homes — Rooted in Southbury. Serving Western Connecticut.
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