Okay this is the chapter I'd print. Three versions of the trip, a 2-day sprint through the Hills, a 4-day one that adds New Haven and Guilford, and a 7-day one that adds the steam train and Mystic and ends in Hartford, laid out day by day with the hours and prices so you can just follow it. They all fly into Bradley, and I built them so the short ones are the first days of the long one, so you can start with the sprint and add days until the budget says stop.
Two date locks before you pick. If you want the Firelight Event in Guilford ($420 pass), days 3 and 4 need to land on Oct 16 to 18. If you want the free Hartford Stars Hollow Weekend on Pratt Street, that's Oct 3 to 4 only. And the state's foliage map has the Hills peaking Oct 14 to 20 this year, so honestly the fan fest weekend is also the leaf weekend, which is either perfect or a crowd.
Give New Milford the whole day. We only had it from about 4:45 until sunset.
The 2-day sprint
Litchfield Hills only. This is the one I'd do if I had a weekend and a plane ticket and nothing else, and it's the version that feels most like the town in the show.
Land at Bradley and drive about an hour and fifteen to New Milford. Breakfast at Theo's Downtown Diner (14 Railroad Street, 6 am to 2 pm, closed Mondays), then walk the green and the bandstand. Fifteen minutes to Washington Depot for Hickory Stick Bookshop (2 Green Hill Road, 9:30 to 5 Monday to Saturday, 11 to 4 Sunday), Marty's, the Washington Food Market, and a drive past the Mayflower Inn grounds on the way out. Then Averill Farm for apples (250 Calhoun Street, 9:30 to 5:30 daily). Sleep at the Litchfield Inn (432 Bantam Road, about $245 to $266) or the Homestead Inn on the New Milford green.
Don't land on a Monday. Theo's is closed Mondays and so is the Villager in Kent, and those are both of your breakfasts. A Friday or Saturday landing gets you both.
Twenty-eight minutes from Washington to Kent. Breakfast at the Villager (28 North Main Street, from 7 on weekdays and 8 on Saturday and Sunday, breakfast until 11:45). Kent Falls ($15 weekend parking for out-of-state plates, $10 weekdays, 8 am to sunset), then Bull's Bridge (free), then Route 7 north to the West Cornwall covered bridge. Back to Bradley, about an hour from Litchfield.
The 50th Kent Pumpkin Run is on the Kent Green that morning, kids fun run at 10:30, the 5-mile at 11, and a costume contest. I'd do the Villager at 8, the run, then the falls and the bridges after.
The 4-day sweet spot
The Hills plus New Haven and Guilford. This is the one I'd tell most people to book, because it gets you the small towns AND the college AND the fan fest if you time it, with about an hour of driving between each piece.
Same as day 1 of the sprint: Theo's, the New Milford green, the Depot and the bookshop and the food market, the Mayflower drive-by, apples at Averill, sleep in Litchfield or on the New Milford green.
Same as day 2 of the sprint, except you're not driving to the airport at the end, so take the Route 7 stretch slow and swing past Lake Waramaug (30 Lake Waramaug Road, $10 weekday or $15 weekend parking) on the way back. Sleep in Litchfield again.
Morning on the Litchfield green, Arethusa Farm Dairy, and the scarecrows at Tapping Reeve Meadow. Then 55 minutes south to New Haven. The free Yale Visitor Center tour (149 Elm Street, register ahead), the Sterling Memorial Library nave before 6 pm, and the Beinecke exhibition hall. Dinner at Pepe's (157 Wooster Street) or Sally's. Sleep in New Haven, The Study at Yale is the one on the fan fest's list.
Sterling's public spaces close to visitors at 6 pm, and the Beinecke is walk-in Monday, Tuesday, and Thursday 9 to 7, Wednesday 10 to 7, Friday 9 to 5, and noon to 5 on weekends. So if day 3 is a Friday, get to campus by mid-afternoon.
Louis' Lunch (261 Crown Street) opens at noon and is closed Sunday and Monday, so this is a late breakfast day. Then 13 miles east to Guilford: the green, the Henry Whitfield House (1639, the oldest house in the state), Bishop's Fall Festival (480 New England Road, 10 to 5, $15 online on a weekend), and lobster at The Place. Fly out of Bradley (44 miles) or Tweed (11 miles).
Put days 3 and 4 on Oct 16 to 18 and this is your Firelight weekend in Guilford, check-in Friday morning. Or put the whole trip on Oct 1 to 4 and swap the Guilford afternoon for the free Hartford Stars Hollow Weekend on Pratt Street, 11 to 5, and fly out of Bradley from there.
The 7-day full immersion
Everything above, plus the steam train, the ferry and the castle, Mystic, and the Emily and Richard part of the trip in Hartford on the way out. This is the one I'd do with my kids, because the added days are the kid days.
Day 1 of the sprint.
Day 2 of the 4-day, with the lake on the way back.
Day 3 of the 4-day: the green and the scarecrows, then Yale before 6.
Day 4 of the 4-day, but you sleep in Guilford or back in New Haven instead of flying, which makes the Oct 16 to 18 festival weekend work.
Essex is 39 minutes from New Haven. The Essex Steam Train & Riverboat (1 Railroad Avenue) runs Thursday through Monday Oct 1 to 25 with departures at 11, 12:30, and 2, and the 2.5-hour train plus riverboat is $49 coach. Lunch or the night at the Griswold Inn (36 Main Street). Then Chester's Main Street and the Chester-Hadlyme Ferry on Route 148 ($5 weekdays, $6 weekends, about five minutes across, runs through Nov 30) over to Gillette Castle.
The train doesn't run Tuesday or Wednesday in October, so if day 5 lands on one of those, flip days 5 and 6 and do Mystic first. Train tickets are non-refundable.
About an hour from New Haven. Mystic Seaport Museum (75 Greenmanville Avenue, 10 to 5, adults $35, youth 4 to 17 $25, half off the last hour), Mystic Aquarium (55 Coogan Boulevard, 10 to 4, book ahead for the cheaper dynamic price), and Mystic Pizza (56 West Main Street). Sleep in Mystic.
An hour and five up to Hartford. The Mark Twain House (351 Farmington Avenue, 9:30 to 5:30, last tour 4:15, $28 adults, $15 kids 6 to 16, under 6 free), where the show's creator started her Connecticut trip, so it's a good place to end yours. Elizabeth Park (free), the big-house drive down Prospect Avenue and Scarborough Street, and the Wadsworth Atheneum if it's Wednesday through Sunday ($24 adults, under 12 free). Fly out of Bradley.
If you want to trade day 7 for Boston and Salem: Hartford to Boston is 100.7 miles, about an hour and 52, and Salem is 32 minutes from North Station on the commuter rail ($3 to $9). But Salem expects about a million visitors in the seven weeks before Halloween, Oct 24 to 25 and Oct 30 are the heaviest days, downtown closes to cars by noon on Oct 31, and Essex Street is closed to traffic on weekends. So only on a weekday, never Oct 24 to 25 or Oct 30 to 31, and by train. It doesn't fit the 4-day trip.
Burbank is its own trip
The town square set (the gazebo, the diner front, the inn, the house) is on the Warner Bros. backlot in Burbank, California (3400 Warner Boulevard), and there's no way to bolt it onto a Connecticut trip. The Studio Tour is $79 for adults and $68 for kids 5 to 10, kids under 5 aren't admitted, and the Stars Hollow stop is included on the tram most tour days, though the route can change for a shoot. Book ahead and arrive 20 minutes early. I'm treating it as a separate weekend and I'd do it in a different season.
How I'd choose
If you've got a weekend, do the sprint and don't feel like you missed the show, because the Hills are the part that made it. If you've got four days, that's the one I'd book for a girls trip and the one I'd put on Oct 16 to 18. If you've got a week and kids, the full version, and sleep in a real bed the night after the train.
Whichever you pick, don't book the Hills nights before mid-October this year. The leaves are running late and the state says peak won't come before mid-to-late October without a hard frost, so I'd hold the Hills nights for the Oct 14 to 20 window and let the flights follow.
So that's the plan, or three of them. For what it's worth, our own version last October was the reverse of all of these, Boston and Salem and Newport first, then Mystic, then New Haven and New Milford in one long day, then Philadelphia, and the one thing I'd change is giving New Milford a whole day and a night instead of ninety minutes at sunset. I mapped these the way I'd want somebody to map one for me, and when we go back for the hills I'll come back and tell you which day was the best one.