This trip works two completely different ways and I want to be honest about both, because the version I'd do with my six kids and the version I'd do with my sisters barely overlap. Same towns, same leaves, totally different days. So this chapter is split. The kids half is a waterfall and corn mazes and a steam train, the girls half is bookshops and inns and a fan festival, and at the bottom there's the version where you spend almost nothing, because I've done that math for six kids more times than I'd like to admit haha.
With kids
Here are the stops I'd build the family version around, with the age rules marked because a couple of them surprised me. And one thing from our own trip first, because it's the thing I'd tell a friend: the greens and the playgrounds are the kid stop. We did New Haven and New Milford in one day with all six kids, and two of my favorite pictures from it are the boys on a playground by the Yale campus and the girls on the bandstand steps on the New Milford green right before sunset. Neither one cost anything. Plan the paid stuff around the free stuff.
The playground, New Haven
The green, New MilfordThe best kid stop in the Hills, and it's short. The trail is 0.84 miles out and back, paved through a covered bridge and then stone stairs a quarter mile up a 70-foot cascade, with platforms so the little ones can stop early. Restrooms, picnic tables, and an ADA path at the base, so this is where I'd do lunch. Open 8 am to sunset.
Out-of-state parking is $15 on weekends and holidays and $10 on weekdays. It's stairs the whole way up, so the stroller stays at the base with the picnic tables.
A swimming beach and picnic areas and a campground, open 8 am to sunset, the let-everybody-out stop after Kent. Same parking setup as the falls, $10 weekdays and $15 weekends. The campground closes at noon on Oct 12 2026, so it's a day stop if you're chasing the mid-October leaves.
Four acres, 30 to 40 minutes to get through, open Sept 5 to Nov 1 2026, weekdays 1 to 5:30 and weekends 10 to 5:30. Adults (13 and up) are $12, kids 4 to 12 are $7, and 3 and under are free. Pick-your-own pumpkins are at their other spot, 105 South Street.
The bigger one, and it's in Guilford on the last afternoon of the 4-day trip anyway. Sept 5 to Nov 1 2026, 10 to 5. A 4-acre corn maze, a pumpkin patch, apple and pear picking (a 4-quart bag is $15), wagon rides on weekends, and bounce pads and a slide and gem mining, which is what my younger ones will want more than the maze if I'm honest. Under 24 months is free.
All-access is $10 online or $13 at the gate on weekdays, and $15 online or $18 at the gate on weekends. For six kids that gap is real, so buy online the night before. And it runs the same weekend as the fan fest in Guilford (Oct 16 to 18), so expect the town to be full.
If I could only add one thing for the kids it'd be this. Oct 1 to 25 2026 it runs Thursday through Monday with departures at 11, 12:30, and 2. The 1-hour train-only ride is $29 coach, and the 2.5-hour train plus riverboat is $49 coach or $65 first class. I'd do the boat version with the kids who can sit that long and the train-only with the ones who can't (I have both kinds).
Tickets are non-refundable, so pick the day after you've looked at the weather. And there's no 2026 pumpkin train in their ticket shop, so don't promise your kids one.
Open 10 to 4. Pricing is dynamic and cheaper in advance, and the exact number only shows up in the booking flow, so I can't give you a figure. I'd book it a few days out once the date is set.
Mystic Seaport Museum (75 Greenmanville Avenue) is open daily 10 to 5 through Nov 1, adults $35, youth 4 to 17 $25, under 3 free, and it's 50% off in the last hour, which with kids who are done by 4 anyway is the ticket I'd buy.
This is where the show's creator started her Connecticut trip, so it's the one history stop I'd make the kids do. Daily 9:30 to 5:30, last tour 4:15. The house tour is $28 for adults and $15 for kids 6 to 16, and under 6 is free. The Living History tour ($31 and $23) is not for under 8, and there's a galleries-only ticket at $8 and $6 for a kid who won't last through a house tour.
Elizabeth Park (1561 Asylum Avenue, West Hartford) is free, dawn to dusk. And if you're in Hartford Oct 3 or 4, the free Stars Hollow Weekend on Pratt Street has a library story hour at 11 am, the one piece of the fan stuff built for small kids.
And the set. The town square set is on the Warner Bros. backlot in Burbank, California, a separate trip, but if you're thinking about it with kids: children under 5 are not admitted to the studio tour at all. So that's a trip for when the baby is five, and I've made peace with that.
Girls trip
Okay this is the one I'd do with my sisters, and it's built on three things: bookshops, one festival, and inns you'd never book with kids.
The bookshops first, because there are four on this route and I'd hit all of them. Hickory Stick Bookshop in Washington Depot (2 Green Hill Road, Monday to Saturday 9:30 to 5, Sunday 11 to 4) has a whole section for the show and stocks Kelly Bishop's memoir, and it was the main attraction for fans at the first fest in 2016. Honeybee Books in New Milford carries Rory's reading list. House of Books is inside Kent Barns. And in New Haven there's Atticus and Book Trader Cafe near campus. Four shops, four towns, and nobody in the van asking if we're done yet.
The Firelight Event, Guilford
This is the original fan fest, the one that started in Washington in 2016 and now runs on the Guilford Town Green. The weekend pass is $420 plus a 3.155% ticketing fee, and it covers 40-plus activities, panels, meet and greets, trivia, tastings, cosplay, and the official t-shirt. Check-in is Friday morning, it wraps Sunday early afternoon, and you pick up your wristband with ID.
The 2026 cast list is Aris Alvarado, Shelly Cole, Artie O'Daly, Emily Kuroda, Rini Bell, Nick Holmes, Grant Lee Phillips (first time back since 2019), and writer Stan Zimmerman. I couldn't find a daily schedule or a kids policy, so I'm treating this as the grown-ups weekend and building days 3 and 4 around it.
Then the inns. The Mayflower Inn & Spa in Washington (118 Woodbury Road) is the one the show's creator stayed at, and it's the splurge, roughly $761 to $3,862 a night on the aggregators, with a wellbeing package from $950. There's a 25% advance-booking discount and a third-night-free deal on their site, which is the only way I'd even look at it. It's 58 acres with a spa and fire pits for s'mores and a boxwood maze, and one reviewer said there's not much for kids to do, which for this version of the trip is fine by me.
The ones I'd more realistically book: the Homestead Inn on the north end of the New Milford green (5 Elm Street) does a full plated breakfast for Main House guests, the Litchfield Inn (432 Bantam Road) starts around $245 to $266 a night, and the Griswold Inn in Essex (36 Main Street) is one of the oldest continuously run inns in the country and sits right where the steam train is.
The cheap version
And then there's the version where you spend like Kirk would, and honestly for a family our size this is closer to what we'd do. Camp. Macedonia Brook State Park in Kent has a campground, and Lake Waramaug's is open through noon on Oct 12, so an early-October trip camps at the lake and a mid-October one is Macedonia Brook. Housatonic Meadows' campground closed Sept 7, though day use there is still free.
Then stack the free stuff. Bull's Bridge and the West Cornwall bridge. The Yale tour (register ahead), the Sterling nave before 6 pm, the Beinecke exhibition hall, the Old Campus courtyard. Elizabeth Park. The Hartford Stars Hollow Weekend on Oct 3 and 4. All the town greens, and the Elephant's Trunk flea market in New Milford is $3 on Sundays. Kids 3 and under are free at Lyman, under 6 at the Twain House, under 12 at the Wadsworth, and the Seaport is half price in the last hour.
For beds, the budget motels I found were running $87 to $108 a night (Southbury, New Milford, Waterbury, Danbury, all listed in chapter 11), quoted for specific dates, so check yours. Skip the festival pass and the inns, pack the pancake mix, and the Hills part of this trip comes down to two parking fees and gas and whatever the kids talk you into at the farm stand.
Which one I'd pick
If I'm being real, both. The girls version first, in the Oct 16 to 18 window, with the festival and the bookshops and one night somewhere with a plated breakfast. Then the family version the next fall, camping, with the train and the falls and the corn maze, once the youngest can do the stone stairs.
What I'd tell you not to do is combine them. Don't drag six kids through a $420 fan festival and don't make your sisters sit through a 2.5-hour riverboat ride in the name of doing it all. It's tempting with a whole week to try, but pick the one you're on and let the other one be next year's.