Okay so there are THREE fan events in Connecticut this fall and they are three different things run by three different groups, and people mix them up online constantly. One costs $420 and is in Guilford on the shoreline. One is free and is in Hartford on a city street. One already happened in New Milford in September. So this chapter is me sorting them out, with the dates and the prices and who's coming, so you can pick your weekend and book before it's gone.
And I'll say this first because it changes the plan. The leaves and the fan events are not on the same schedule this year. DEEP's map has the Litchfield Hills peaking Oct 14 to 20 and the shoreline (where Guilford is) not until Oct 28 to Nov 3, and the free Hartford weekend is Oct 3 to 4, when the Hills will probably still be green. So you're going to have to decide what you're here for, and I lay out how I'd split it at the end.
New Milford green
October in the hillsThis is the original one. It started as the Gilmore Girls Fan Fest in Washington Depot in 2016, run by Jennie and Marcus Whitaker, and it's been The Fan Fest Society since 2021. It's moved around, Washington Depot, then Kent, then Maine twice, and now Guilford, where last year went well enough that the town approved the Green again this year (with the Guilford Fairgrounds as the backup venue).
The 2026 weekend pass is $420 plus a 3.155% ticketing fee, and for that you get what they describe as 40-plus themed activities, panels, meet and greets, trivia, tastings, cosplay and the official t-shirt. Check-in is Friday morning, it wraps up Sunday by early afternoon (their pages say 1 pm in one place and 2 pm in another), late registration is open all weekend, and you pick up your wristband with ID.
The 2026 cast and crew list for Guilford: Aris Alvarado (Caesar), Shelly Cole (Madeline), Artie O'Daly, Emily Kuroda (Mrs. Kim), Rini Bell (Lulu), Nick Holmes (Robert), Grant Lee Phillips (the town troubadour, first time back since 2019), and Stan Zimmerman, who wrote for the show. I'll be honest, the troubadour is the one that got me, and if you've watched the fall episodes as many times as I have you probably had the same reaction when you read that name.
Getting there, per the organizers: Tweed New Haven is 11 miles, Bradley (BDL) is 44, LaGuardia 71, JFK 73, Boston 141. You can do Metro-North to New Haven and then Shore Line East to Guilford, but they say themselves they'd suggest renting a car, and so do I. Their lodging list is short and it's the one I'd book from: Red Roof and Comfort Inn in Guilford, Beech Tree Cottages, Madison Beach Hotel and Scranton Seahorse Inn in Madison, Holiday Inn Express in Branford, Westbrook Inn and Water's Edge in Westbrook, The Study at Yale in New Haven, River Wind Inn in Deep River, and Copper Beech in Ivoryton.
$420 a person before the fee. For a family of eight that's not a thing, so this is a girls-trip weekend for me, and I couldn't verify a kids policy either way, so ask before you bring littles. I also couldn't confirm whether it's sold out or how close, and the first year sold out fast, so if you want this, buy the pass and then book the room, in that order.
Guilford is worth the weekend even without the fest, and chapter 9 covers it. The short version is a 7.7-acre green, the Henry Whitfield House from 1639, and Bishop's Fall Festival at 480 New England Road, which runs through Nov 1 with a corn maze and a pumpkin patch, $15 online or $18 at the gate on weekends. If somebody in your group isn't going to the panels, that's their Saturday.
This one is FREE and I love it for that reason alone. It's the third year the city has done it, Saturday Oct 3 and Sunday Oct 4, 11 to 5 both days, on Pratt Street downtown, with trivia and look-alike contests and a vendor market and flash tattoos and dance classes and fall crafts. It's also billed as The Great Pratt Street Autumn Festival, with a stage schedule that has a library story hour at 11 am, a cabaret, a barbershop quartet and line dancing. So it's a city fall festival with a fan weekend inside it, which honestly for a family is the better shape, because the kids who don't care about the show still get a street fair.
This is the one I'd do with all six kids. It's free, the story hour is at 11 so you can build a morning around it, and it's in the same city as the Mark Twain House, where the creator's trip started (chapter 8 has the Hartford day and this fits right into it).
Oct 3 to 4 is early for leaves. DEEP's map doesn't have northern Connecticut turning until Oct 14 to 20, and the UConn forestry guy said peak won't happen before mid-to-late October without a hard frost. So if you come for this weekend, come for the weekend and Hartford, and don't drive up to the Hills expecting the photo, because you'll most likely get a green with green leaves on it and a long drive back.
This one is a town event rather than a fan event, and that's why it's on this list. It's the 50th year of the Kent Pumpkin Run, on the Kent Green on Sunday, Oct 25, with the 5-mile race at 11 am, the Kids Fun Run at 10:30, and a costume contest. A town race with a costume contest on a green in late October is as close to an episode as any of the three fan events, and I don't have the registration price, so check kentct.com. Chapter 4 has the Kent day built around it if your trip lands on that weekend.
A Weekend in the Life (New Milford)
A Weekend in the Life is run by Decade Days in New Milford, and the 2026 edition was Sept 4 to 6, so it's over. It was the third time they've done it (April 2025, September 2025, September 2026), the venues were Town Hall, the Town Green, the high school and St. John's Church, and the 2026 guests were Scott Patterson, Sean Gunn, Chad Michael Murray and Matt Czuchry, with autographs and panels and trivia and bingo and a karaoke pajama party and a murder mystery in Town Hall. September 2025 tickets started at $49.77, and I don't have the 2026 prices.
There are no 2027 dates announced. I'm not going to guess whether it comes back, but I'd keep an eye on newmilfordnow.org, and if it lands on that green again with the bandstand in the middle, it's the one I'd want to bring the kids to. I'll update this page when they post.
The fairs list
These are from CT Public's 2026 fairs list and I've only verified the dates. Harwinton Fair, Oct 2 to 4, Litchfield County. Southington Apple Harvest Festival, Oct 2 to 4 and Oct 9 to 11 (the apple fritters are the thing). Riverton Fair, Oct 9 to 11. Connecticut Garlic & Harvest Festival, Oct 10 to 11, 304 Main St N, Bethlehem, next door to Woodbury (chapter 5). Glastonbury Apple Harvest Festival, Oct 16 to 18, the same weekend as Firelight. Putnam Great Pumpkin Festival, Oct 17. And the Kent Pumpkin Run above on Oct 25. On the cheap version of this trip, a county fair on a Saturday is a whole day for a family for less than one Firelight pass.
How I'd pick
If you're a fan first and the leaves are a bonus, it's the Firelight weekend, Oct 16 to 18. Fly into BDL or Tweed, do the Hills on the Wednesday and Thursday before (the Oct 14 to 20 peak window is right there), and then drive down to Guilford for Friday check-in. That's the 4-day sweet spot in chapter 12 with the Guilford days locked to the fest. The shoreline leaves won't be at peak on the 16th, but you'll have had the Hills at peak two days earlier, and I think that's the best combination the calendar offers this year.
If you've got a big family and $420 a head isn't happening, it's Hartford, Oct 3 to 4. Do the free weekend, do the Mark Twain House ($28 adults, $15 kids 6 to 16, under 6 free), do Elizabeth Park (free), and don't expect leaves. Then do the Hills the following weekend if you can stretch it, because Oct 14 is only ten days later.
If you just want the small-town feeling and none of the fan stuff, it's the Kent Pumpkin Run on Oct 25, with the Hills a little past peak and a town race on a green. That's the version I'd pick for my own family if I'm being honest, because it's the cheapest and the kids get a fun run.
A note on the names
You'll notice the fan fest calls itself The Firelight Event and the Hartford one is run by a city, and neither of them puts the show's name in the title. That's on purpose, and it's why this guide is called Small Town Fall. Warner Bros. went after a Connecticut non-profit over shirts with the show's clips and marks on them and the court sided with the studio, so the events keep it descriptive and so do I.
The dates on this page are the ones I'd build a trip around this year, and they're the reason I'm putting this guide out now instead of waiting until we go back for the hills. If any of them change I'll update here first.