title with a fair

Fair Season in Connecticut: Your Local Guide to the Southington Apple Harvest Festival (and the Rest of October)

September 29, 2026•4 min read

You know it's fall in Connecticut when you leave the house in a fleece and come home carrying it.

And when your entire weekend plan is "fried dough, then we'll see."

Fair season is officially here. Durham already came and went (and yes, we're still thinking about that parking field). But the best stretch is still ahead of us.

It kicks off Friday, October 2, in Southington.

Southington Apple Harvest Festival 2026: The Basics

If you've lived here more than one fall, you already know. If you're new, here's the quick version.

  • When: Two weekends. Friday, October 2 to Sunday, October 4, and Friday, October 9 to Sunday, October 11

  • Where: Southington Town Green, 75 Main Street

  • Cost: Free admission

  • Crowd: Over 100,000 people. So bring your patience :)

  • Fun fact: This is year 57. It's been running since 1969.

It's one of the biggest and longest running festivals in the Northeast. And it still feels like a small town event, which is kind of the magic of it.

What to Actually Do There

Eat an apple fritter. Then eat a second one for research purposes.

Work your way through the apple menu. Pie, crisp, cider, candy apples, apple everything. Nobody's counting.

Ride the carnival. Kids love it. Adults who just had two fritters should maybe sit this one out.

Shop the craft vendors. Good time to knock out a few holiday gifts before November sneaks up on you.

Catch the parade. Sunday, October 4 at 2 p.m. It starts at Knowles Avenue and Summer Street in Plantsville and ends on Eden Avenue. Rain date is Sunday, October 11.

Take a history break. The Barnes Museum is running cemetery walking tours at 10 a.m. on both Saturdays (October 3 at Oak Hill Cemetery, October 10 at the South End Burying Ground in Plantsville). Suggested donation is $10. The museum also offers free first floor tours from 1 to 5 p.m. both Saturdays. Perfect if you want something a little spooky season adjacent.

Local Tips the Official Website Won't Tell You

Go Friday night or early Saturday. If crowds aren't your thing, beat the Saturday afternoon rush.

Mind the parade day parking. On October 4, there's no parking along the parade route from 7 a.m. to 10 p.m. The fine is $35 and they will tow. Southington PD is not bluffing.

Queen Street will be Queen Street. Plan your route like it's a normal Saturday, then add fifteen minutes.

Dress in layers. It'll be 45 degrees at 9 a.m. and 68 by 1 p.m. Your kid will hand you their sweatshirt by 11.

Bring some cash. Card readers and festival Wi-Fi have a complicated relationship.

The Rest of Fair Season (Connecticut and Next Door)

Southington isn't the only game in town. Here's what else is still on the calendar.

The Big E (West Springfield, MA)
Runs through Sunday, October 4. Technically Massachusetts. Spiritually, all of New England. Get the cream puff. Don't argue with us.

Topsfield Fair (Topsfield, MA)
October 2 to 12. It's been around since 1820, and it's home to the All New England Giant Pumpkin Weigh-Off. Worth the drive if you've never seen a pumpkin the size of a small hatchback.

Riverton Fair (Riverton, CT)
October 9 to 11. Known as the last country fair of the season, and it's been going since 1909. Small, old school, and exactly what a Litchfield County fair should be.

Missed Durham this year?
Mark your calendar now. It's always the last full weekend in September.

Why We Love This Stuff (A Realtor's Take)

Here's something we've learned from years of helping people buy and sell here.

Nobody falls in love with a town because of its mill rate.

They fall in love because of the town green. The parade. The neighbor who's been working the same booth for 30 years and still remembers your kid's name.

That's a big part of why Southington stays in demand. You get:

  • A real downtown with real traditions

  • Easy access to I-84 and Route 691

  • A reasonable drive to Hartford, Waterbury, and New Haven

  • Neighborhoods like Plantsville and Milldale that each have their own feel

And it's not just Southington. Connecticut home values were up 4.9% over the past year, compared to 2.0% nationally (per Zillow, as of August 22). Turns out a lot of people want what we've got.

Fritters included.

Heading to the Green? Say Hi.

If you catch yourself walking past those houses on the side streets and wondering what they go for, that's honestly our favorite question.

Thinking about buying? Selling? Just curious what your place is worth now? Reach out. We'll give you the honest read. No strings, and no sales pitch between fritters.

And if you know someone who just moved to Connecticut and needs the full fair season briefing, send them this. Consider it their welcome packet.

See you on the green. 🍎

@brooketeamofficial

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David Brooke

David Brooke has been helping buyers and sellers move across Connecticut and Massachusetts for over a decade. He writes New England Nests to explain the parts of a transaction most people only learn about at the closing table.

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