Okay so before we get to the towns I need to tell y'all the real story, because the real story is better than the version most people have in their heads and it changes how you plan the whole trip. Also I want to be up front about what I have and haven't done. Last October we spent three days of our six-week fall road trip in Connecticut, Mystic and New Haven and New Milford, and the New Milford part is the whole reason this guide exists. The Litchfield Hills loop (Washington Depot, Kent, Litchfield) and Hartford we did not get to, the sun went down on us in New Milford and we had to be in Philadelphia the next day. So chapters 3, 7 and 9 have our photos and our mistakes in them, and the rest is mapped and checked the same way, with every address and hour and price verified this September. I'll tell you which is which as we go.
New Milford, October 28
The map on the bookshop wallAbout 25 years ago Amy Sherman-Palladino and her husband took a trip to Connecticut. It started at the Mark Twain House in Hartford (which is the only reason Hartford is on this trip at all, more on that in chapter 8) and then they ended up in Washington, a tiny town in the Litchfield Hills, in October. She stayed at the Mayflower Inn there. And what she saw is basically the show, pumpkin patches and hay rides and the fall colors and a little town where everybody seemed to know everybody.
Her own words were that it was beautiful and magical, a feeling of warmth and small-town camaraderie, and that there was a longing for that in her own life. She talked about a diner where somebody walked behind the counter and poured their own refill because the waitress was busy, and locals asking each other where the pumpkin patch was, and how everything looked like it was covered in sugar. You guys. That's the town. That trip is where the look of the show came from.
So the town on the show isn't one real town. Wikipedia lists Washington, West Hartford and New Milford as the inspirations, and Washington's own tourism site says she fell in love with the town while she was staying at the Mayflower. Which means this trip is a loop through the Litchfield Hills with a couple of side trips down to New Haven and the shoreline, and honestly that's why it works as a road trip. You're driving between four or five little towns on back roads in October and the driving is half of it.
Nothing was filmed here
This is the part that surprises people, so I'm putting it right up top. Not one episode was filmed in Connecticut. CT Public spelled it out in their piece on the towns, and I'm going to say it twice because it matters when you're booking flights. The town square you know, the gazebo and the diner front and the inn and the house, all of that was built on the Warner Bros. backlot in Burbank, California, on a street called Midwest Street. And it's still there. You can go stand on it, it's part of the regular studio tour.
So if the photo you want is you on the gazebo steps, that's a Los Angeles trip and it's a separate trip (I put the details below and again in chapter 12 so nobody books the wrong flight haha). What Connecticut has is the feeling she was chasing. The real greens and the real diners and a bookshop that's been there 60 years, the stuff she was picturing when she wrote it. I think that's the better trip, but I want you to know exactly what you're signing up for before you buy a ticket.
This is where her trip started, so it's where the story starts. It's open daily 9:30 to 5:30 with the last tour at 4:15, and the house tour is $28 for adults and $15 for kids 6 to 16, with under 6 free. There's a Living History tour too ($31 and $23, and they don't take kids under 8 on that one) and if you just want the galleries it's $8 for adults and $6 for kids. I'm saving the full Hartford day for chapter 8, that's the Emily and Richard part of the trip, but if you fly into BDL you're already in Hartford and I like the idea of starting where she started.
This is the set, the real one, and it's on the other side of the country. The tram on the Studio Tour stops at Midwest Street and you get the gazebo and the town notice board and the diner exterior and the inn exterior and the house exterior, all included with the standard ticket. It's available most tour days but the route can change if something's shooting, so it's never a guarantee. The Studio Tour runs 8:30 am to 3:30 pm, it's about 45 to 60 minutes guided plus around two hours on your own, and the Studio Store sells show apparel if you need a sweatshirt.
Last winter for the 25th anniversary they dressed Midwest Street as a snowy version of the town, Dec 18 2025 through Jan 4 2026, included with regular tickets, and Scott Patterson kept showing up unannounced. I looked hard and there is NO fall 2026 event announced, so please don't plan around one. If it repeats I'll update this page.
Tickets are $79 for adults (11 and up) and $68 for kids 5 to 10, with the Plus tour from $160 and the Deluxe from $330. Kids under 5 are not admitted, which matters if you've got littles. Book ahead, get there 20 minutes early, and the tour is closed Nov 3 to 5 and Nov 26 in 2026.
When to go
Okay this is the part where I get bossy. Do NOT book this trip for early October. I know, the show made all of us think October 1 is peak everything, but Connecticut's foliage runs later than that most years and 2026 is running later still. The state's environmental department (DEEP) says color starts in late September and runs through early November, and their peak window statewide is Oct 3 through Nov 8. Their Sept 17 forecast said this year would be later and more colorful than usual, and their map puts the northern part of the state, which is the Litchfield Hills where most of this trip lives, at Oct 14 to 20, the middle of the state at Oct 21 to 27, and the shoreline and New Haven at Oct 28 to Nov 3.
A forestry guy at UConn, Thomas Worthley, said it best, if things stay warm the leaves stay green, and that peak won't happen before mid-to-late October without a hard frost. So my rule for this one is don't book before mid-October. If you can only do one weekend, the Oct 16 to 18 weekend puts you in the Hills during the DEEP peak window and it's also the Firelight fan fest weekend down in Guilford, and Oct 25 is the Kent Pumpkin Run. The free Hartford fan weekend is Oct 3 to 4, which is lovely, but the leaves will probably still be green up in the Hills that weekend, so go in knowing that. Chapter 6 has all three laid out.
Weather-wise, Hartford's normal October is a high of 63 and a low of 41, so it's sweater and puffy vest weather in the day and cold at night. Pack layers, y'all, and I'd throw in rain gear just in case.
What to rewatch
I'm not going to give you an episode list because y'all have your own and mine would just be the fall ones anyway haha. But I do think you should rewatch a few before you go, specifically the episodes where the town square is done up for fall, because you want the bandstand and the notice board and all the leaves in your head when you pull up to the New Milford green. It lands differently that way. And rewatch a few of the Emily and Richard scenes before the Hartford day, because the big houses on Prospect Avenue make a lot more sense when she's fresh in your mind.
One more, and this is a small one. The first fan fest was held in Washington in 2016 and it sold out within minutes, and the fest has moved around since then (Kent, then Maine twice, now Guilford). So if you're going on the Firelight weekend, read chapter 6 before you read anything else, because the pass is $420 and the lodging list is short and it's all in there.
The honest version
So here's what I want you to know going in. These are real towns and they're small. Washington is under 5,000 people and it was incorporated in 1779, and the cell service up there is limited (there's free Wi-Fi at the parking area in the Depot, which tells you something). The diner in New Milford closes at 2 and the bookshop in the Depot closes at 5. There's no set to walk onto. What you get is the green and the church steeple and a bakery and a family grocery and people going about their Tuesday, and I think that's the part she was longing for in the first place.
I'll also say, the Mayflower Inn is a splurge on a level that made me laugh out loud (chapter 2 has the numbers), so if you're picturing yourself sleeping where she slept, do a drive-by and then go get a room at the Homestead Inn on the New Milford green like a normal person. And if you have a big crew like we do, a lot of this is free. The greens are free and Bull's Bridge is free and the Yale tour is free and the whole Hartford fan weekend is free, and I'll flag the free stuff in every chapter.
I built this the way I build all of our trips, with the map open and the kids' ages in mind and a real budget, and with the three towns we already did as the anchor. I'm putting it out now because the dates matter this year and I'd rather y'all have it in time to book. When we go back for the hills (and we're going back, I have a diner to eat at) I'll add those photos too, and you'll already own it.