Say Yes Gilmore Girls
A Cozy Gilmore Girls Weekend in 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.
A small group designed to feel easy, personal, and unhurried.
Accommodations, meals, transportation during the trip, activities, and photography are all included.
October 22–25, 2026 | 4 Days, 3 Nights | Litchfield Hills, Connecticut
By booking, you agree to our Trip Terms & PoliciesDates
Oct 22-25, 2026
Location
Litchfield Hills, CT
Group Size
Up to 6 travelers
Investment
$1,600 per person
Why October?
Why Fall in Connecticut Feels Different
October in Connecticut feels cinematic. The summer crowds disappear, the leaves turn amber and red, and every small town suddenly feels quieter, slower, and softer around the edges.
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 Our Days Will Look Like
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.
Mornings
Coffee at The Courtroom
Wandering quiet town centers
Afternoons
Covered bridges
Kent Falls picnic
Antique bookstores
Evenings
Dinner at Marty’s
Slow nights back at the house
Accommodations
Your Home For The Weekend
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. Shared rooms are thoughtfully arranged so everyone still has their own comfortable space to recharge.
What's Included
The goal is simple: once you arrive, you shouldn’t have to think about logistics.
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 Don’t Have To Document Everything
A professional photographer will be with us throughout the weekend, so you can stay fully present instead of documenting everything yourself.
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
Who This Trip Is Really For
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: $1,600 per person
Note: Because these trips are intentionally small, all bookings are nonrefundable. If something changes, you’re welcome to transfer your spot to another traveler.
Say Yes
Come Spend the Weekend With Us
A small-group fall weekend designed to feel slow, cozy, and fully taken care of.
$1,600
Pay in Full
Per person, paid today
$800
Reserve with Deposit
Today, then $800 due July 24, 2026By booking, you agree to our Trip Terms & Policies