Fall is hands-down my favorite season. It means cooler days, sweaters, pumpkins, warm drinks, and cozy evenings. And during those cozy evenings? I often rewatch Gilmore Girls. Seasons 1-6 (we don’t talk about Season 7), endless cups of coffee, and that small-New England-town magic that makes you want to pack up and move to Stars Hollow immediately.
Of course we all know Stars Hollow isn’t real. It was filmed on a Warner Brothers backlot in California. But the vibe? The charm? The fall foliage and town greens and quirky local festivals? That’s 100% inspired by real New England towns.
And the best part? You can actually visit them.
So grab your coffee (preferably from Luke’s… or, you know, a local café), put on your coziest flannel, and let’s find the real-life Stars Hollow in Connecticut, Vermont, and beyond.
The Towns That Inspired Stars Hollow
Creator Amy Sherman-Palladino has said she was inspired by several New England towns when creating Stars Hollow. The most commonly cited? Washington Depot, Connecticut—a tiny town she visited and immediately fell for. But the magic of Stars Hollow is really a blend of several quintessential New England villages.
Here’s where to find that Gilmore magic in real life.
Connecticut: Where It All Began
Washington Depot
This is ground zero for Stars Hollow vibes. Washington Depot is tiny (population under 400), charming, and has that perfect New England town green that feels straight out of the show.
What to do:
- Walk around the tiny downtown—it takes about 10 minutes, but soak in that small-town atmosphere
- Visit The Hickory Stick Bookshop (Rory would definitely spend hours here)
- Have lunch at G.W. Tavern or grab pastries at Marty’s Café
- Drive through the surrounding countryside—rolling hills, stone walls, gorgeous fall colors
Real talk:
Washington Depot doesn’t have tons of shops or activities. That’s kind of the point. It’s quiet, understated, and perfect for just… existing in that New England small-town bubble for a bit.
Kent
Just 30 minutes from Washington Depot, Kent is another contender for Stars Hollow inspiration. It’s slightly bigger, with a cute main street full of antique shops, galleries, and cafés.
Don’t miss:
- Kent Falls State Park – Stunning waterfall, especially beautiful in fall
- Fife ‘n Drum Restaurant – Upscale American cuisine in a historic inn
- Browse the antique shops and art galleries along Main Street
Bonus:
Kent has a covered bridge (Bulls Bridge) that’s absolutely worth the detour for photos.
Litchfield
Litchfield takes the “charming New England town” thing to another level. The town green is picture-perfect, the historic homes are impeccably preserved, and the whole place feels like it’s been frozen in the best possible time period.
What to do:
- Walk around Litchfield Green
- Visit The Litchfield Historical Society if you’re into local history
- Shop at Patina for home goods (very Lorelai’s taste)
- Lunch at The Village Restaurant – local favorite for decades
Where to stay:
Winvian Farm (just outside Litchfield in Morris, CT) – This isn’t your typical New England inn. It’s 18 themed cottages on 113 acres, and it’s absolutely over-the-top in the best way. Each cottage is individually designed (there’s a Helicopter cottage, a Stable cottage, a Library cottage…). It’s luxury meets whimsy, and it’s perfect for a special celebration or romantic escape.
Stars Hollow-Adjacent: Essex & Chester
These Connecticut River towns have that same quaint energy, with the added bonus of scenic train rides and river views.
- Essex Steam Train & Riverboat – Vintage train ride through fall foliage (very Kirk Gleason energy)
- Chester – Adorable Main Street with cafés and boutiques
Vermont: Peak Fall Magic
While Connecticut has the towns that directly inspired Stars Hollow, Vermont has the feeling—those postcard-perfect villages, covered bridges, and mountain backdrops that make you feel like you’re living inside a Gilmore Girls episode.
Woodstock
If Stars Hollow had a slightly more upscale cousin, it would be Woodstock. The village green, the covered bridge, the white-steepled church—it’s all here, and it’s all ridiculously charming.
What to do:
- Cross the Middle Covered Bridge (Lorelai would 100% have opinions about this bridge)
- Browse F.H. Gillingham & Sons General Store – operating since 1886, it’s like Doose’s Market but real
- Visit Billings Farm & Museum for that New England pastoral vibe
- Walk around the village green and admire the historic homes
Where to stay:
The Woodstock Inn & Resort – Historic luxury property right on the green. Fireplaces, farm-to-table dining, spa, and serious fall ambiance.
Stowe
Stowe is what would happen if Stars Hollow was a mountain town. It’s got the charming main street, the fall colors, and the cozy inns—plus actual mountains in the background.
What to do:
- Walk the Stowe Recreation Path (perfect for a mother-daughter power walk)
- Ride the gondola up Mount Mansfield for panoramic fall views
- Visit Von Trapp Family Lodge (yes, THAT Von Trapp family—very musical-episode-of-GG vibes)
- Grab coffee and pastries at Butler’s Pantry
Where to stay:
The Lodge at Spruce Peak – Luxury mountain resort with a spa, gourmet dining, and that upscale-rustic vibe Lorelai would appreciate.
Manchester
Manchester has upscale shopping (hello, designer outlets), gorgeous fall scenery, and excellent restaurants. It’s basically what Stars Hollow would be if it had more money.
What to do:
- Browse Northshire Bookstore – independent bookshop with cozy reading nooks (Rory’s heaven)
- Shop the Manchester Designer Outlets if that’s your thing
- Hike to Lye Brook Falls for fall foliage
- Have dinner at The Reluctant Panther Inn – upscale, romantic, seasonal menu
The Gilmore Girls Experience: What to Actually Do
1. Town Green Picnics
Pack a picnic (or grab takeout from a local café) and spend an afternoon on a town green. Bring a book, people-watch, soak in that small-town energy.
Best town greens:
- Litchfield, CT
- Woodstock, VT
- Grafton, VT (bonus: incredibly photogenic)
2. Coffee Shop Culture
Find a local coffee shop and become a regular (even if just for a weekend). Order the same thing every time. Make awkward small talk with the owner. Channel your inner Lorelai.
Recommendations:
- Provisions in Washington Depot, CT
- Butler’s Pantry in Stowe, VT
- The Norwich Inn in Norwich, VT (upscale brunch vibes)
3. Quirky Town Festivals
Okay, you probably won’t find a 24-hour dance marathon or a Founders’ Day Punch reenactment, but New England towns LOVE their fall festivals.
Be on the lookout for:
- Apple festivals
- Pumpkin patches
- Harvest fairs
- Oktoberfests
Pro tip:
Check local event calendars before you go. Town festivals are peak New England charm and often involve cider donuts, which is really all that matters.
4. Used Bookstores
Channel your inner Rory and spend hours in independent bookstores.
Must-visit:
- The Hickory Stick Bookshop (Washington Depot, CT)
- Northshire Bookstore (Manchester, VT)
- The Book Barn (Niantic, CT) – Not on the typical route, but if you’re a book person, it’s worth the detour
5. Covered Bridges & Scenic Drives
Rent a car, pick a scenic byway, and just drive. Stop at farm stands. Take photos at covered bridges. Get slightly lost and discover tiny towns you’ve never heard of.
Best drives:
- Route 100 in Vermont (runs north-south through the heart of the state)
- Litchfield Hills Loop in Connecticut
- Smugglers’ Notch in Vermont (dramatic mountain pass)
6. Cozy Inn Stays
Find an inn with a fireplace, a good restaurant, and that lived-in charm. The kind of place where they know your name by the second morning and the coffee is always hot.
Favorites:
- Winvian Farm (Morris, CT) – Over-the-top luxury cottages
- The Woodstock Inn (Woodstock, VT) – Classic New England elegance
- The Mayflower Grace (Washington, CT) – English country house vibes
- Twin Farms (Barnard, VT) – All-inclusive luxury (seriously splurge-worthy)
Sample 4-Day Stars Hollow Adventure
Day 1: Arrive in Litchfield, CT
- Explore Litchfield Green
- Check into Winvian Farm or Mayflower Grace
- Dinner at The Village Restaurant
Day 2: Washington Depot & Kent
- Morning in Washington Depot (bookshop, coffee, wandering)
- Drive to Kent for lunch and antique shopping
- Stop at Kent Falls on the way back
- Cozy evening at your inn
Day 3: Drive to Vermont (Woodstock)
- Scenic drive up to Vermont (about 3 hours)
- Check into The Woodstock Inn
- Explore the village, walk across the covered bridge
- Dinner at The Prince & The Pauper
Day 4: Woodstock & Stowe
- Morning at Billings Farm
- Drive to Stowe (1 hour)
- Gondola ride or Recreation Path walk
- Coffee at Butler’s Pantry
- Head home (or extend your stay—Vermont is hard to leave)
When to Go
Peak Gilmore Girls Season:
Late September through October. Peak foliage, apple picking, pumpkin everything, and that crisp fall air that makes you want to live in a flannel shirt forever.
Late October (when you’re reading this):
Still gorgeous, tail-end of foliage, but way fewer crowds. Plus, inns start offering off-season rates which means luxury for less.
Pro tip:
If you’re trying to avoid weekend crowds, go Tuesday-Thursday. Small towns are quieter, restaurants are easier to book, and you’ll have those town greens practically to yourself.
The Real Magic
Here’s the thing about chasing Stars Hollow: you’re not going to find it. Not exactly.
What you will find is something even better—real New England towns with their own quirks, their own histories, their own coffee shop regulars and town gossips and annual festivals. You’ll find fall foliage that’s even more stunning than the show made it look. You’ll find inns where the owners actually remember your name. You’ll find that slower pace of life that makes you wonder why you’re rushing through everything back home.
And if you’re lucky, you’ll find yourself sitting on a town green with a cup of coffee, watching the leaves fall, feeling like maybe—just maybe—you’ve stepped into your own version of Stars Hollow after all.
If you want help planning a Gilmore Girls-inspired New England escape—finding those hidden-gem towns, booking the coziest inns, timing your trip for peak fall magic—let’s talk. This is genuinely one of my favorite trips to plan.
Copper boom.
