Kent is the day I'm most excited about, honestly, and it's the one with the least to do with the show. There's a 70-foot waterfall and two covered bridges and a diner that opens at 7 and a drive up Route 7 that National Geographic Traveler called one of the most scenic in the country, and all of it is 28 minutes from Washington Depot. If you only get one full day in the Hills and the leaves are doing their thing, this is the day I'd protect.
The show connection is thinner here than in the Depot or New Milford, so I'll just say it once. After the first fan fest sold out in Washington in 2016 it moved to Kent for 2017, and Kent is on the state's own list of fall stops with the Pumpkin Run and the Eric Sloane Museum and Seven Hearths. But you're not coming here for the connection. You're coming because this is the same corner of the Litchfield Hills she was staying in that October, and the leaves along the Housatonic are what I'd drive across the country for.
So here's the version I mapped out, in driving order. It's a full day with six kids, and with two adults and no kids it's a morning and an afternoon with a long lunch in the middle haha.
Bull's Bridge, Kent
Kent Falls
West Cornwall bridgeThis is where I'd eat breakfast in Kent. It opens at 7 on weekdays (Tuesday through Friday, 7 to 4) and 8 on Saturday and Sunday (8 to 4), and breakfast is served until 11:45, which is the number that matters if you're the kind of family that gets out of the inn later than planned (we are that family, I've made peace with it). Tuesdays they also do dinner from 4:15 to 8:30, and the number is (860) 927-1555. I'd go here first, before the falls, because the falls are a climb and I want everybody fed before we start up stone stairs.
Closed Mondays. And the weekend opening is 8, so if you're doing Kent on a Saturday, don't roll up at 7:15 with hungry kids like I would have. Breakfast stops at 11:45 per their site, so plan it as a morning stop.
Okay this one is FREE. Bull's Bridge was built in 1842 and it's one of the few covered bridges left in Connecticut that you can still drive across, single lane, 109 feet over the Housatonic River. It's been on the National Register since 1972. There's free parking and a short walk to the bridge and the rapids under it, and the trails from here connect to the Appalachian Trail if you've got a kid who needs to burn something off.
There's a story that George Washington crossed here, and it's legend, so I'll tell my kids it's a legend and let them decide. The rapids are the part I think the little ones will remember, and the bridge photo is the one I'll remember.
The heritage site warns that the walk is narrow and slippery after rain, and October in Connecticut has rain. Put everybody in real shoes and hold hands with the small ones near the water.
The Barns are the galleries and shops in town, and House of Books is in there, which means this is the third bookshop on this trip and I'm not sorry about it. I'd give this an hour after the bridge, let everybody walk around, and pick up lunch in town before the falls. I don't have hours for the Barns so treat it as a daytime stop and check before you count on a specific shop.
Fife 'n Drum and Swyft (wood-fired pizza) are the two lunch names that came up in the write-ups I leaned on, and pizza with six kids is never the wrong call. The Eric Sloane Museum and Seven Hearths (a house from 1751) are the two history stops on the state's Kent list if you've got a kid who likes old houses, and Macedonia Brook State Park has camping if you're doing this the cheap way.
This is the one. The falls drop about 70 feet in a cascade, and the trail is a 0.84-mile out-and-back, so it's short, but it's stairs. You walk a paved path through a covered bridge (yes, another one, this trip is basically a covered bridge collection) and then it's stone steps for a quarter mile up alongside the water with viewing platforms along the way. So you can stop at the first platform with the stroller crowd or push to the top with the big kids. There are restrooms and picnic tables and an ADA path at the base, which is why I'd plan lunch here instead of in town if the weather's good.
It's open 8 am to sunset. With the leaves turning I'd try to be here in the early afternoon so the light's still on the water, and I'd budget more time than the trail length suggests because everybody stops on every platform.
Out-of-state parking is $15 on weekends and holidays and $10 on weekdays, so if you're coming from Utah like us, that's you. Cash or card I couldn't confirm, so bring both. And it's stairs the whole way up, so if you've got somebody who can't do a quarter mile of stone steps, the base of the falls with the picnic tables is still a good stop.
From Kent Falls you stay on Route 7 north and this is where the drive turns into the reason you came. The state's own foliage list names Route 7 up to Housatonic Meadows and Route 128 to the West Cornwall bridge as two of the best stretches in Connecticut, and the DEEP map puts this part of the state at peak Oct 14 to 20 this year. The bridge itself is the red one, built around 1864, one lane, 172 feet across the Housatonic. It's the picture in your head when somebody says covered bridge in New England, and honestly I'm going to have to be talked out of making the kids do a photo in matching flannel on it.
The state's full Route 7 leaf route runs Ridgefield to Falls Village and they call it a 1 to 2 day drive. I'm only doing the Kent to West Cornwall piece, because that's the part with the falls and both bridges, and then turning around.
Housatonic Meadows State Park (90 US-7, Sharon) is on the way and day use is free with access to the river off Route 7, so it's an easy pull-off if the kids need out of the van. The campground there closed for the season on Sept 7 2026 though, so don't plan on sleeping there.
On the way back toward Washington I'd swing past Lake Waramaug, which has a swimming beach and picnic areas and a campground, and is open 8 am to sunset. In October nobody in my family is swimming (okay maybe one of them, there's always one) but a lake with fall color around it at the end of a day like this is the kind of stop where you let everybody out and don't set a timer.
Out-of-state parking is $10 weekdays and $15 weekends, same setup as Kent Falls. And the campground closes for the season at noon on Oct 12 2026, which is BEFORE the leaves peak up here. So if you were planning to camp and chase the Oct 14 to 20 window, this one doesn't work for you, and Macedonia Brook in Kent is the one to look at instead.
Kent Pumpkin Run
This is the 50th year of the Kent Pumpkin Run and it's on the Kent Green on Sunday, Oct 25. The 5-mile race starts at 11 am, the Kids Fun Run is at 10:30, and there's a costume contest, which with my crew is the main event and the running is secondary.
If your trip lands on that weekend I'd flip the Kent day to Sunday, do the Villager at 8, get the kids to the green for the 10:30 fun run, and then do the falls and the bridges after. The leaves will be past peak in the Hills by the 25th according to DEEP's map, but late color on a race morning is still color, and a 50th anniversary town race is the kind of small-town thing this trip is about. Check kentct.com for registration, I don't have the price.
How I'd run the day
Villager at opening, Bull's Bridge while it's still quiet, the Barns and a bookshop, lunch, then Kent Falls in the early afternoon and Route 7 north to West Cornwall with the light going gold. Back down through Kent to Lake Waramaug, and then 28 minutes to Washington or 30 to Litchfield for the night, depending on which day of the sprint you're on (chapter 12 has both). The two parking fees are $30 total on a weekend for out-of-staters, and Bull's Bridge and the West Cornwall bridge are free, so this is a $30 day plus food if you skip the museums.
With little kids I'd cut the West Cornwall drive if the falls took everything out of them, and save it for a second day. With a girls trip I'd skip the lake and keep driving north toward Falls Village, because nobody's asking when we're stopping.
This is the day I don't have a show fact for, and I'm okay with that. The waterfall and the bridges were here long before the show, and I think they're the closest thing on this trip to what she saw out the car window.