This is the town. If you only get one afternoon in Connecticut and you're a fan, this is where I'd spend it, because Washington is where Amy Sherman-Palladino stayed on the trip that turned into the show, and it's still under 5,000 people and still built around a green and a bookshop and a family grocery that's been there over a hundred years.
A little geography first because it confused me when I was mapping this. Washington is the town (incorporated 1779) and Washington Depot is the little downtown part with the shops, and the Mayflower is out on Route 47 a few minutes away. The Depot is 8.8 miles from New Milford, about 15 minutes, and about an hour and 15 from the Hartford airport, and the town's own site says it's under two hours from New York City and under three from Boston. So it's close to everything and it feels like it's close to nothing, which I think is why she loved it.
The town's tourism site says she fell in love with Washington while staying at the Mayflower Inn & Spa, and the first fan fest was held here in 2016. That fest drew 1,200 people to a town of under 5,000, sold out within minutes, and the next year it moved to Kent (chapter 6 has the current version, which is down in Guilford now). So the fans have been coming for a decade and the town has had a decade to get used to us.
One thing before you drive up. Cell service is limited up here and there's free Wi-Fi at the parking area in the Depot, so download your maps before you leave New Milford. Please. Six kids and no signal and a wrong turn is not the vibe.
Washington Depot
The Litchfield HillsThis is the inn where she stayed. It's part of the Auberge Collection now, 58 acres, about 35 rooms (28 rooms and 7 suites), with Cafe Boulud on site and a spa called The Retreat and an outdoor pool and tennis and fire pits for s'mores and walking trails and a Shakespeare garden with a boxwood maze. It sounds like the inn on the show because I think in a lot of ways it IS the inn on the show, or at least the feeling of it.
Okay now the numbers, and I need you to sit down. The aggregator range I found was $761 to $3,862 a night with an average around $2,187. Their own site has a wellbeing package from $950 a night, a 25 percent discount for booking ahead, and a third-night-free deal. One reviewer also said there's not much for kids to do, which honestly tracks, it's a grown-up place. So here's how I'd do it. Drive Route 47 past it, look at the grounds from the road, and then go sleep somewhere that costs a tenth of that. If it's a girls trip and somebody's paying, the third night free is the one to look at.
At those rates, if you're doing it, book far ahead and use the 25 percent advance-booking discount. And if you have littles, the reviews say this isn't the place for them, and at two thousand dollars a night I wouldn't bring mine anyway haha.
This is the first real stop and honestly it's the one I'm most excited about. Hickory Stick has been in business for 60-plus years, it has its own Gilmore Girls section, and it stocks Kelly Bishop's book, The Third Gilmore Girl, which is the one I'd buy here so it has the receipt from this town in it. When the fan fest came through in 2016 this shop was the main attraction, which for a bookshop in a town this size is a big deal.
Hours are Monday through Saturday 9:30 to 5 and Sunday 11 to 4, and the number is (860) 868-0525. I'd get here right at 9:30 so you have the place mostly to yourself.
The town's own fan list also has Five Janes for clothing, Washington Supply Company, the hardware store, and Bryan Memorial Town Hall, and all of it is walkable from the bookshop.
Marty's is the breakfast stop, breakfast and lunch with pastries and paninis, and the town's site says its friendly atmosphere will remind you of the show's favorite place. That's the town saying it, and I'll take it. If you slept in New Milford and ate at Theo's already, come here for a pastry mid-morning and call it second breakfast (my kids would be thrilled).
I could not confirm Marty's hours or street address, so call ahead at (860) 868-1700 before you plan a meal around it. The Depot is small enough that you'll find it, but don't roll up at 3 pm expecting lunch.
A family grocery that's been going for more than a hundred years, and it's the one on the town's list that reads like the show's market. This is the stop I'd make for van snacks and apples and whatever the kids are begging for, because honestly the best way to see a town like this is to buy your groceries in it. It's on the town's own fan list so they know why you're there.
The Pantry (you'll also see it as Weston's Bakery) is the lunch stop, and the way the local guides split it is Marty's for breakfast and The Pantry for lunch, so that's how I mapped it. Bakery plus lunch is my favorite kind of place on a trip because half the kids want a sandwich and half want a cookie and everybody wins.
The green is the picture in your head. The Po Cafe is on the green if you want a burger, and the Frederick Gunn School (a prep school) is part of the town too, which is the prep-school side of the show if you squint. I'd park and walk it and let the kids run, and I'd do it in the afternoon light if you can swing it. This is a real town green with real people using it, so it's a walk and a photo and that's plenty.
This is the apples stop and it's the one my kids will care about most. Averill Farm is open 9:30 to 5:30 daily and the number is (860) 868-2777, and the orchard entrance is at 262 Calhoun, a little past the main address. Remember the story about locals asking each other where the pumpkin patch was? This is the kind of place she was talking about, and I'd give it a full hour with kids.
Open 9:30 to 5:30 daily, so it works as a last stop before you drive to Litchfield for the night, but don't cut it close, 5:30 comes fast in October.
The year the fans showed up
The very first fan fest was held here in Washington in 2016. It drew 1,200 people and sold out within minutes, and the next year they sold 1,750. So 1,200 fans in a town of under 5,000 was a lot, and the fest moved to Kent in 2017, then to Maine for two years, and it's in Guilford now under the name The Firelight Event.
So Washington doesn't host the fest anymore, and honestly I think that's why it's the better town to visit. You get the bookshop and the green and the grocery on a normal fall day without a crowd. If you want the crowd, chapter 6 has the Oct 16 to 18 details and the $420 pass.
How I'd do the day
Sleep in New Milford, eat breakfast at Theo's (6 to 2, closed Mondays), and drive the 15 minutes up so you're at Hickory Stick when it opens at 9:30. Buy the book. Walk the Depot with a pastry from Marty's and pick up snacks at the Food Market, then lunch at The Pantry, then the green, then Averill for apples until you've had enough. Somewhere in there drive Route 47 past the Mayflower and let yourself gawk. Then it's about 30 minutes to Litchfield, where the Litchfield Inn runs from around $245 to $266 a night, or go back to the Homestead Inn on the New Milford green.
With my crew I'd flip it and do Averill first while everyone still has patience, because a bookshop with six kids is a very different experience at 9:30 am than at 3 pm. Your mileage may vary. If it's a girls trip, do it in the order above and linger at the bookshop as long as you want.
I'll be honest that this is the town I'm most nervous about getting right, because it's the one she picked, and it's small, and I want us to be good guests in it. Buy something and eat there and don't block the road for a photo. The town has had fans coming through for ten years now and I'd like us to be the easy kind.