Litchfield is the town on this trip I'd pick if somebody made me pick one for the leaves. The state's own foliage people name the Northwest Hills around Litchfield as one of the best regions in Connecticut, the DEEP map has it peaking Oct 14 to 20 this year, and the town itself is a late 18th-century green with shops and restaurants around it, a dairy, a bakery, and a meadow full of scarecrows in the fall. It's 30 minutes from Washington Depot and about an hour from the airport, which is why it's night two in almost every version of this trip I built.
And then Woodbury is the antiques town. More than two dozen shops on one road, a Saturday flea market, and an inn that bills itself as the oldest in Connecticut. I'm putting them in the same chapter because they're the same kind of day, slow and shoppy and mostly outside, and because I know some of y'all are here for the antiques and some of y'all are here for the scarecrows and I want both of you to get your day.
Honest note up front. I have fewer hours and prices for this chapter than for the others, because a lot of these are small-town stops that don't post them anywhere I could verify. Where I don't have an hour I'll say so, and you should call before you drive.
Litchfield
The hills in OctoberThis is the third green on the trip, and the state describes it as late 18th-century with shops and restaurants right on it. I'd start here in the morning, walk it, and let it be the slow part of the day. The Litchfield History Museum is on the state's list for the town too, and I'd send the history kid in there while the rest of us look at leaves.
For food, the names that came up were The Village Restaurant, West Street Grill, Litchfield Saltwater Grille, Market Place Tavern and @ the Corner. I don't have hours for any of them. I'd pick whichever one is open when we're hungry, which is how most of our trips go anyway haha.
Topsmead State Forest is on the state's Litchfield list along with White Memorial (stop 5) if you want two outdoor stops instead of one. I don't have details on Topsmead so I'm only giving you the name.
Okay so this is the one I'm most excited about in Litchfield, and it's a little embarrassing how much. The Tapping Reeve House is the old law school (the state lists it as one of the town's historic sites), and in the fall the meadow next to it fills up with scarecrows for a contest. A meadow. Full of scarecrows. In a town with a green and a steeple in the third week of October. If you've watched the fall episodes as many times as I have you already know why I'm losing it about this.
I'd let each kid pick a favorite and vote, and I'd take way too many photos, and I'd be fine spending an hour here that the schedule says should be twenty minutes.
I could not find the 2026 dates for the scarecrow contest, and I'm not going to guess. It's a fall thing, it came up on the fall stop list I used, and that's all I can promise. Check with the Litchfield History Museum before you build a day around it, especially if you're coming the last week of October.
Arethusa is the dairy, and it's on the fall stops list for the town along with their bakery, Arethusa a mano, which is over in Bantam (the Litchfield Inn is on Bantam Road, so you'll be over that way if you're sleeping there). I don't have a menu or hours, so I'm not going to tell you what to order, but I will say that a dairy in the afternoon with six kids in the van is a stop I never skip, and I'm going in expecting something cold and sweet. If I'm wrong I'll update this page.
A bakery on the fall stops list, and y'all know I'm not passing a bakery in a town like this. I don't have hours or an address beyond the town, so I'd hit it in the morning after the green, when bakeries are safest, and grab whatever the kids point at for the drive to White Memorial. That's honestly all I've got on it, and I'd rather tell you that than make something up.
White Memorial is the conservation center on the state's Litchfield list, and it's the outside part of the day. After a green and a bakery and a dairy I need to get everybody moving, and a conservation center in the Hills during peak leaves is where I'd do it. I don't have trail lengths or hours for it, so I'm planning it as an open-ended afternoon stop and I'd check their site for what's open in October and whether there's a fee.
If you're doing the 4-day version, this is the last stop before the 55-minute drive down to New Haven, so I'd keep it to an hour or so and get on the road with the light.
Woodbury is the antiques town, and the state's antiques trail page says there are more than two dozen shops along Old US 6, with Woodbury Pewter, Antiquario and M. Shay as the named ones. This is a girls-trip stop for me, because I can't picture six kids on an antiques row, and with a big van the question is always going to be whether the thing I find fits behind the third row.
It's not on the day-loop the rest of the Hills chapters follow, so treat it as a detour. I don't have a drive time from Litchfield for you, so look at the map before you commit, and I'd give it a half day if you're a serious antiques person and an hour if you're just curious.
The Glebe House Museum and the Gertrude Jekyll Garden are on the same state page, and the 1754 House Inn is billed as Connecticut's oldest inn if you want to sleep in Woodbury instead of Litchfield. I don't have a rate for it, so you'll have to look that one up.
The antiques flea market at Route 64 is Saturdays only. If you're an antiques person and you can only do Woodbury one day, make it a Saturday, and get there in the morning, because the good stuff at a flea market is usually gone by lunch.
Connecticut Garlic & Harvest Festival
This one is in Bethlehem, the next town over from Woodbury, at 304 Main St N, on Saturday and Sunday Oct 10 and 11. It's a garlic festival. I don't know what to tell y'all except that it's on CT Public's list of fall fairs and I think a garlic festival in a town called Bethlehem is exactly the kind of thing this trip is for. I don't have prices or hours for it, so check before you go.
Two more from the same list for this part of the state. The Harwinton Fair is Oct 2 to 4 in Litchfield County, and the Riverton Fair is Oct 9 to 11. I haven't verified either one beyond the dates, but if your trip is early October (which, chapter 1, the leaves probably aren't turned yet) a county fair is a good reason to be up here anyway.
Where I'd sleep in Litchfield
The Litchfield Inn at 432 Bantam Road is the one I keep coming back to. It was quoting from $266 a night when I checked, with an outdoor pool (not that we're swimming in October) and a restaurant, and Tripadvisor had Litchfield hotels starting around $245. The other names that came up were The Abner Hotel, Belden House & Mews and Lost Fox Inn, and I don't have rates for those. For a family this is the mid tier, and chapter 11 has the whole spread from the Mayflower down to the $87 motel.
If you're doing the 2-day sprint, Litchfield is night one (after the Depot and Averill Farm) and Kent is the next morning. If you're doing the 4-day, Litchfield is the morning of day three before New Haven. Either way, the drive from BDL to Litchfield is 38.9 miles and about an hour and four minutes, so it also works as your first stop if you'd rather sleep here on arrival and do New Milford the next day.
One more honest thing
This chapter has more "I don't have hours for that" than I'd like, and I thought about cutting the stops I couldn't fully verify. I left them in because they're all on lists from the state or from Connecticut writers who've done this trip, and because a scarecrow meadow and a dairy and a bakery on a green are the stops y'all would be mad at me for leaving out. Just call ahead. Small towns close early and close on odd days, and I'd rather you know that from me.
The green and the leaves don't have hours, so those are the two things I'm planning the Litchfield day around, and everything else is something I'll be glad about if it's open when we get there. We didn't make it up here on our trip (New Milford ate the afternoon, chapter 3 explains), so this chapter is the mapped and checked version, and when we go back for the hills I'll fill in what I'm missing.