Say Yes: Gilmore Girls Fall Weekend
October 22–25, 2026 | Litchfield Hills, Connecticut
Pack your flannel, grab a coffee, and cue the la-la-las.
Spend a long fall weekend wandering through the real towns that inspired Stars Hollow. Sip coffee at cozy cafés. Walk across historic bridges. Browse small bookshops while the leaves change all around you. This is for anyone who has ever wished they could step into an episode of Gilmore Girls and live it for real.
Four slow, soul-filling days. Seven like-minded women. Coffee, connection, and the kind of laughter that lingers.
Travel with a professional photographer so you can stay present in every moment and go home with portraits that remind you how it felt to be fully there.
Our Weekend Together
For four days, you will trade busy for intentional. We will explore small towns that feel like home the moment you arrive. You will wander through covered bridges, listen to the sound of waterfalls, and linger in cafés that could double as Luke’s. You will not need your phone because I will photograph the warm light, the laughter, and the feeling of being fully present.
Thursday: Welcome to Connecticut
Arrive in Hartford with a suitcase full of sweaters and that first-day excitement that comes with something new. Our cozy home in the Litchfield Hills is waiting. Coffee is brewing. Candles are flickering. The hum of women settling in for a weekend that already feels special.
That evening, we will head into downtown Litchfield for dinner at The Corner Café, where laughter fills the room and the air smells like butter and baked bread. The night ends slowly with a book, new friends, and that soft knowing that you are exactly where you are meant to be.
Friday: Bridges, Waterfalls, and Cafés
The morning begins with strong coffee and easy conversation at The Courtroom, the kind of place where the locals know each other by name. Then we wander toward the West Cornwall Bridge, a red wooden beauty stretched across the river and the perfect place to pause and breathe it all in.
From there, we continue to Kent Falls State Park for a short walk beneath the trees and a picnic lunch by the sound of rushing water. The rest of the afternoon unfolds in small-town perfection. Antique stores, cozy bookshops, and a stop at 45 on Main for sweets and caffeine refills. We return to the house for dinner and a relaxed night in, hearts full and spirits light.
Saturday: A Day in Stars Hollow
This is your Stars Hollow day. We begin with coffee at River and Rail Café in New Milford, then stroll to the town green and the gazebo that inspired the one we all know by heart. You will stand there with your coffee while I capture the moment you have dreamed of.
The day takes us through Washington Depot, the real-world home of Luke’s Diner, Doose’s Market, and the Independence Inn. We will browse Hickory Stick Bookshop, chat with locals at The Po, and wander the gardens at the Mayflower Inn, where time seems to slow down just for us. We finish with dinner at Marty’s Café and ice cream at Arethusa Dairy because every good story deserves a sweet ending.
Sunday: Coffee and Goodbyes
The final morning comes softly. Coffee cups clink, sleepy smiles appear, and gratitude hangs in the air. We will share one last breakfast, swap numbers, and promise to meet again somewhere else the world decides to take us next.
You will leave with new friendships, beautiful portraits, and the calm that comes from saying yes to yourself.
What’s Included
Three nights in our private home in the Litchfield Hills
All meals eaten out at local cafés, diners, and taverns
All group activities, hikes, and entry fees
Ground transportation during the trip
Professional photos of you in all your Stars Hollow moments
Time to slow down, laugh hard, and connect deeply
Not included: flights to and from Connecticut, personal shopping, and travel insurance
Why This Retreat Is Worth Saying Yes To
Say Yes trips are created for women who crave connection, comfort, and the kind of experience that fills your soul, not your schedule. They are designed to help you slow down, feel inspired again, and remember what it is like to be fully present.
Connecticut in the fall is the perfect setting for that pause. The air is crisp, the leaves are turning, and the world feels softer. You will wander through small towns that look like movie sets, laugh over coffee with women who feel like old friends, and finally have photos of yourself in the moments you never want to forget.
You will head home with new friendships, beautiful portraits, and a reminder that slowing down is not falling behind. It is finding your rhythm again.
If your heart is craving something cozy, creative, and real, this is your sign to say yes.
Trip Details
Location: Litchfield Hills, Connecticut
Dates: October 22 to 25, 2026
Duration: 4 days and 3 nights
Group Size: 7 guests plus 1 host
Rooming: Shared accommodations with individual beds. Two queen beds are available for guests who bring a friend to share and save.
Private Bed Price: $1049 per person
Bring a Friend Price: $949 per person (limited to two shared pairs)
Important Note: Due to the nature of small group retreat planning, refunds are not available. You may transfer or sell your spot to another traveler if needed. While Say Yes cannot guarantee a resale, we will share your available spot with our community and waitlist to help you connect with someone.
Ready to Say Yes to Stars Hollow?
If your heart beats faster at the sound of coffee being poured or you’ve ever dreamed of wandering the streets of Stars Hollow, this trip was made for you.
Fall leaves, small towns, and warm company are waiting.
$1049 per person
Perfect for solo travelers who want their own bed and space to recharge after a full day of exploring.
✔️ 3 nights lodging in a shared room with an individual bed
✔️ All meals
✔️ All activities and transportation
✔️ Professional photos throughout the retreat
Bring a Friend discount – $949 per person
Share a queen bed with your best friend, sister, or fellow Gilmore Girls fan and save.
✔️ 3 nights lodging in a shared queen bed
✔️ All meals, activities, and transportation included
✔️ Professional photos of you both living your Lorelai and Rory dreams
Please note: both guests must register separately and list each other as roommates so we can pair your booking.
