Say Yes Gilmore Girls
Live the Episode You've Always Wanted to Be In
October 22–25, 2026 | 4 Days, 3 Nights | Litchfield Hills, Connecticut
You know that feeling when an episode ends and you just want to stay there a little longer? That is what this trip is.
We are spending four days in the real Connecticut towns that inspired Stars Hollow. Covered bridges. Cozy cafés. Fall leaves turning gold along quiet roads. Every meal handled, every moment photographed, and nowhere you have to be except exactly where you are.
Five spots. Small group. The kind of weekend you will talk about for years.
By booking, you agree to our Trip Terms & PoliciesDates
Oct 22-25, 2026
Location
Litchfield Hills, CT
Group Size
Up to 6 travelers
Investment
$1,300 per person
Why October?
Why Say Yes to Connecticut in October
Connecticut earns it in October. The leaves turn amber and red, the air gets crisp, and every small town looks like it was decorated just for this weekend. It is the kind of scenery that makes you stop mid-sentence to take it in.
October means we miss the summer crowds and land in the sweet spot before the holidays arrive. The towns are peaceful, the cafés have open tables, and the light in the late afternoon is genuinely extraordinary to photograph.
This is not a trip about checking boxes. It is about slowing down enough to actually feel somewhere new, with people who chose to show up the same as you did.
The Experience
What We'll Experience Together
Every day of this retreat is intentional and unhurried. No rushing between attractions, no racing to fit everything in. Just four days of wandering beautifully through one of the most cinematic corners of New England.
Highlights include:
Morning coffee at The Courtroom, the kind of local café where everyone knows each other
Walking the West Cornwall Covered Bridge, one of the most photographed spots in Connecticut
A picnic lunch by the waterfalls at Kent Falls State Park
Browsing antique shops, independent bookstores, and 45 on Main for afternoon sweets
Standing on the town green in New Milford where the Stars Hollow gazebo was born
Exploring Washington Depot, the real-world home of Luke's Diner and Doose's Market
Browsing the Hickory Stick Bookshop and wandering the gardens at the Mayflower Inn
Dinner at Marty's Café and ice cream at Arethusa Dairy to end the perfect day
Slow evenings back at the house with new friends and nowhere to be
Accommodations
Where You'll Stay
Our home base is a private house in the Litchfield Hills, tucked into the kind of New England landscape that feels borrowed straight from a movie set. We are not staying in a hotel. We are staying somewhere that actually feels like Stars Hollow.
Think wood floors, morning light pouring into the kitchen, and the smell of coffee from the moment you wake up. Rooms are shared with your own personal bed, so you have a comfortable, private space to recharge at the end of each full day.
What's Included
3 nights in our private Litchfield Hills home
Every meal throughout the trip, from Thursday dinner through Sunday breakfast
All activities, hikes, and entry fees
Ground transportation for the entire weekend
Professional photography throughout the retreat
A curated itinerary, so all you have to do is show up
What’s Not Included
Flights to and from Connecticut
Travel insurance (strongly recommended)
Personal shopping and souvenirs
Meals
Every Meal Is Taken Care Of
From Thursday dinner to Sunday morning coffee, every meal is included. That is not an accident. It is part of what makes this feel like a real retreat rather than just a trip.
We are eating at the kind of places Stars Hollow would be proud of. Diners with good pie. Cafés where the owners remember your order. And evenings back at the house where dinner winds down slowly over something warm and a conversation that keeps going longer than anyone expected.
You show up hungry. Everything else is handled.
Professional Photos
You Will Actually Be In the Photos
I'm Macey, a professional photographer with 18+ years of experience, and I am on every single trip.
That means you can put your phone in your pocket and stay completely present. No stopping to document moments you should be living. No asking strangers to take photos that never turn out right. I will be there the whole time, capturing the covered bridges, the café window light, and the look on your face when you are standing on the cozy gazebo, holding a coffee, feeling like Lorelai Gilmore.
You will leave with a full gallery of professional portraits that capture how this weekend actually felt.
Fit Check
Is This Trip For You?
This trip was made for you if:
Gilmore Girls has been in your rotation more times than you can count
You are craving something slow, cozy, and genuinely restorative
You want to travel without the mental load of planning every detail
You love fall foliage, small towns, and the smell of old bookshops
You are ready for a trip where someone else handles everything
You are coming solo and excited to meet the women who said yes alongside you
You are bringing someone you love and want a memory worth keeping
A heads up: this is a walking weekend. We explore on foot through towns, along trails, and across bridges. Nothing extreme, but comfortable shoes are a must, and the pace will keep you moving.
Let’s Recap
Trip Details
Location: Litchfield Hills, Connecticut
Dates: October 22–25, 2026 (3 nights, 4 days)
Accommodations: Private home in the Litchfield Hills
Group Size: Up to 6 travelers
Investment: $1,300 per person
Note: Due to the nature of small group retreat planning, refunds are not available. You may transfer or sell your spot to another traveler. Say Yes will share your available spot with our community and waitlist to help you connect with someone.
Investment
Ready to Book?
There are only 5 spots available. Every detail is handled. All you have to do is show up.
$1,300
Pay in Full
Per person, paid today
$650
Reserve with Deposit
Today, then $650 due July 24, 2026By booking, you agree to our Trip Terms & Policies