Okay, the money chapter, and here's the straight version: how you get to Connecticut from somewhere far away (I'm in Utah, so far away is my whole life), how long the drives are, what the inns and motels and campgrounds cost with the real numbers I could find, and what a 4-day version of this trip adds up to before you've bought a single pancake. I don't have a flight or rental car price in here, because those swing so much by date that anything I wrote today would be wrong by the time you read it.
Getting there
Bradley (BDL) in Hartford is the airport for this trip. Aer Lingus, American, Breeze, Delta, Frontier, JetBlue, Southwest, Sun Country, and United all fly there, and it's 49.6 miles and about an hour and fifteen to Washington Depot, or 38.9 miles and an hour and four to Litchfield. There is NO nonstop from Salt Lake City to Bradley, which I looked at three times hoping I was wrong. Bradley has nonstops to Denver on Southwest and United and to Las Vegas on Breeze, so from Utah I'd plan a connection and stop being sad about it.
Tweed New Haven (HVN) is the little one, Avelo and Breeze only, about 40 destinations and mostly Southeast and Florida. It's 11 miles from Guilford though, so if the fan fest is your whole reason for coming, it's the closest airport by a lot.
The New York airports work too. LaGuardia is 71 miles from Guilford and JFK is 73, and the drive from the city to Washington Depot is 85 miles, about 2 hours. There's a Metro-North option to Wingdale (20 miles from Washington) or Dover Plains (24 miles) and then a taxi, but the fan fest organizers themselves say they'd suggest renting a car, and so would I. None of the good stuff (Bull's Bridge, Kent Falls, Averill Farm, the West Cornwall bridge) is on a train line, and the towns are 15 to 30 minutes apart, and the drive between them is half of why you're going.
How far everything is
The Hills part is tight, which is what makes the 2-day version work. Washington Depot to New Milford is 8.8 miles, 15 minutes. Washington Depot to Kent is 15.5 miles, 28 minutes. Litchfield is about 30 minutes from Washington. The loop the state suggests (New Milford green for breakfast, then Washington Depot, then Kent for the falls and the bridge, then Route 7 north to West Cornwall, then back through Litchfield) is one long day of short drives.
Then it stretches out. Litchfield to New Haven is 37.6 miles, about 55 minutes. New Haven to Guilford is about 13 miles. New Haven to Essex is 31.9 miles, 39 minutes. New Haven to Mystic is 55 miles, an hour and two. Mystic back to Hartford is 54.7 miles, an hour and five, which is why the 7-day trip ends in Hartford and flies out of Bradley instead of backtracking. So it's a loop, Bradley to the Hills to New Haven to the shoreline and back up to Hartford, and you never drive the same road twice except Route 7, which you'll want to.
Where to stay
Four tiers, from the inn the show's creator stayed at down to a tent. The quoted motel rates are for specific dates, so treat them as a range and check your own.
Gillette Castle
Essex Steam TrainThis is the one. She stayed here, she fell in love with the town, and the rest is the show. It's an Auberge property on 58 acres with Cafe Boulud on site, a spa, an outdoor pool, fire pits for s'mores, walking trails, and a Shakespeare garden with a boxwood maze, and only about 35 rooms (28 rooms and 7 suites). The aggregator range was $761 to $3,862 a night with an average around $2,187, and the inn's own wellbeing package starts at $950 a night. The number is (866) 217-0869.
Their site lists a 25% advance-booking discount and a third-night-free deal, so if you're doing it, book early and do three nights. One reviewer said there's not much for kids to do. If you're not staying, drive the grounds on the way out of the Depot and don't feel bad about it.
This is where I'd sleep the first two nights. From $266 a night on one site and Litchfield hotels from $245 on another, so call it $245 to $266, with an outdoor pool and a restaurant, 30 minutes from Washington and an hour and four from Bradley. Litchfield also has The Abner Hotel, Belden House & Mews, and Lost Fox Inn if it's full.
North end of the New Milford green, so you walk to the bandstand and to Theo's for breakfast, and Main House guests get a full plated breakfast. Their site has a whole section for fans of the show. I couldn't find a nightly rate, so check it against the Litchfield Inn and pick whichever green you'd rather wake up on.
For the 7-day trip, this is the night after the steam train. It's one of the oldest continuously run inns in the country, on Main Street in Essex. No rate on file.
For the New Haven and fan fest nights, the organizers' own lodging list is The Study at Yale, Red Roof and Comfort Inn in Guilford, Madison Beach Hotel and Scranton Seahorse Inn in Madison, Holiday Inn Express in Branford, Westbrook Inn and Water's Edge in Westbrook, River Wind Inn in Deep River, and Copper Beech in Ivoryton. No prices from them, but that's where I'd start for Oct 16 to 18.
This is the tier my family lives in. The quotes I found for specific October dates were the Wyndham in Southbury at $87, the Maple Leaf Motel in New Milford at $89, the Courtyard in Waterbury at $99, and the La Quinta in Danbury at $108. The Maple Leaf is the one I'd look at first because it's in New Milford, 15 minutes from the Depot.
Those are one-night quotes for particular dates, and mid-October is when the leaves peak up here, so it fills. With two adults and six kids we'd need two rooms, so double whatever you see, and book the Oct 16 to 18 weekend early.
Macedonia Brook in Kent has a campground and it's the one that works for the mid-October leaf window. Lake Waramaug's campground (30 Lake Waramaug Road) is open through noon on Oct 12 2026, so it's an early-October option only. Housatonic Meadows on Route 7 in Sharon closed its campground on Sept 7 2026, though day use there is free.
Hartford's normal October is a high of 63 and a low of 41. So camping in the leaf window means real sleeping bags, and I'd have a motel picked out as the backup for the night it rains.
A realistic 4-day budget
Here's how I'd add it up for the 4-day trip in chapter 12 (two nights in the Hills, one in New Haven, out of Bradley on day 4), before flights, the rental car, gas, and food. Two versions, because a girls trip and a family our size are different math.
Two people, mid tier. Two nights at the Litchfield Inn at $266 is $532. I don't have a rate for the New Haven night, so I'm penciling in the same $266, which puts lodging around $800. Then the day stuff: Kent Falls parking $15 on a weekend, Lake Waramaug $15, Bishop's Fall Festival $15 each online on a weekend, and the Yale tour, Sterling, Beinecke, Bull's Bridge, the West Cornwall bridge, and every town green free. So about $860 for beds and admissions. If you're going for the Firelight Event, add $420 plus the 3.155% fee, about $433 a person, so two passes takes it to roughly $1,730 before you've eaten.
Two adults and six kids, budget tier. Two motel rooms at around $90 each for three nights is about $540. Parking at the two parks is $30 for the weekend. Bishop's at $15 online for two adults and six kids is $120. The Yale tour and the greens and the bridges are free. So call it $690 for beds and admissions, and if you camp at Macedonia Brook instead it drops to the campground fee, which I couldn't find, plus that $150 in parking and farm tickets. No festival pass in this version, because I'm not paying $433 times eight for a weekend the kids won't sit through haha.
Neither number includes airfare, the car, gas, or food, and food with six kids is its own line item that I'm not going to pretend I can estimate for you. The park parking is out-of-state pricing ($15 weekends, $10 weekdays), so a weekday trip saves $10 at each gate.
What I'd tell you about the money
The trip itself is cheap, which surprised me building this. Almost everything that makes it feel like the show, the greens and the bandstand and the bookshop and the covered bridges and the drive up Route 7, costs nothing or costs a parking fee. The money is in the bed and in getting there, and you get to decide how much of each.
So my honest advice is to spend on one night that feels like the show (the Homestead on the green, or the Litchfield Inn, or if it's a big birthday, the Mayflower with the third night free) and go cheap on the rest. And book the beds before you book the flights. Mid-October in the Hills, with the leaves peaking and a fan fest on the shoreline the same week, is going to fill up, and the flights will still be there once you've got the room.