A Gilmore Girls Guide to Fall in Cortland County

Welcome to Cortland County, aka your own Stars Hollow for the weekend. If your ideal fall involves Gilmore Girls levels of coffee consumption, cozy bookstores, small town festivals and a quintessential autumn weekend itinerary, you're in the right place.

This is the season for pulling on your favorite flannel, grabbing the Lorelai to your Rory (or the Luke to your Lorelai) and setting off in search of cider doughnuts, colorful backroads and charming small towns where there always seems to be something happening on the village green.

There is only one acceptable way to begin a Gilmore Girls inspired fall day: caffeinated.

Fortunately, Cortland County takes coffee almost as seriously as Lorelai. Find a cozy corner, order something pumpkin spiced and make approximately 47 plans for the day before finishing your first cup.

Gilmore Bucket List: Drink enough coffee to concern Luke.

CUE THE LA-LA-LAS: Click here to find local coffee shops 

Counter stools. Chocolate chip pancakes. Bottomless coffee. And server who already knows the regulars. All the ingredients of a Luke worthy diner.

Forget the fancy brunch reservation. Fall calls for a good old fashioned diner, and Cortland County has plenty of places where the pancakes come hot off the griddle and somebody is always walking around with a fresh pot of coffee.

Gilmore Bucket List: Find your own Luke’s Diner.

CUE THE LA-LA-LAS: Click here to check out our local diners.

Would Rory Gilmore ever walk past an independent bookstore without going inside? Yeah, exactly.

So, pop into All My Friends Books in downtown Cortland, browse the shelves and pick out something to keep you company when the weather turns chilly. You probably did not need another book, but ask yourself "what would Rory do?" and buy it anyway.

Gilmore Bucket List: Find a cozy read Rory would approve of.

CUE THE LA-LA-LAS: Click here to visit All My Friends Books 

Every fall wardrobe needs a good flannel. Bonus points if it looks like it could have survived several shifts at Luke’s and an argument with Taylor Doose.

Dig through the racks at Lot 1 Vintage for vintage flannels, denim, band tees and plenty of pieces worthy of a Stars Hollow fall. Then throw on your new find, stuff a book in your back pocket and look mildly bored by the beautiful fall day. Very Jess.

Gilmore Bucket List: Find a flannel worthy of Luke. Wear it like Jess. Backward hat optional. 

CUE THE LA-LA-LAS: Click here to visit Lot 1 Vintage 

Some fall traditions need no explanation. At Hollenbeck’s Cider Mill, fresh pressed cider and cider doughnuts have been bringing people through the doors for generations. Add apples, pies, local cheese and a crisp Upstate New York afternoon, and you have the sort of fall stop Lorelai and Rory could turn into an entire meal. Don't forget to grab another dozen for the road! 

Gilmore Bucket List: Eat too many cider doughnuts (or maybe half a pie) and call it lunch.

CUE THE LA-LA-LAS: Click here to visit Hollenbeck’s Cider Mill

If Sookie and Jackson planned a fall date, there would definitely be fresh produce involved. Stroll through a Cortland County farmers market and fill your bag with crisp apples, just picked vegetables, local honey, baked goods and whatever else looks too good to leave behind.

Gilmore Bucket List: Shop the farmers market like Sookie is planning the menu.

CUE THE LA-LA-LAS: Click here to find Cortland County farmers markets.

No town does fall quite like a town with a festival committee.

On October 3 and 4, downtown Cortland goes full Stars Hollow for The Great Cortland Pumpkinfest, with pumpkins (of course), delicious food, vendors, live music, rides and enough autumn enthusiasm to keep Taylor Doose armed with a clipboard all weekend. Go all in, borrow a favorite sweater and take the cute pumpkin photo. Attendance at this quintessential town festival is practically mandatory.

Gilmore Bucket List: Attend a small town festival Taylor would take way too seriously.

CUE THE LA-LA-LAS: Click here for The Great Cortland Pumpkinfest 

Make your way to the Village Green in Marathon, where a picture perfect gazebo sits amongst the historic downtown in the heart of this tiny Upstate New York village. When the leaves begin to change, it has all the ingredients for a Stars Hollow moment. Take a stroll around the green, snap a cute photo and, if the mood strikes, give twirl worthy of a Ms. Patty performance. She'd approve.

Gilmore Bucket List: Have your Stars Hollow gazebo moment.

CUE THE LA-LA-LAS: Click here to explore Marathon 

Mrs. Kim did not play around when it came to antiques. Neither should you.

Cortland County is filled with places to dig through antique furniture, vintage décor, forgotten treasures, old Paul Anka records, and the occasional object you suddenly, absolutely can not live without. And just maybe, "yet another chair you can't sit in."

Gilmore Bucket List: Find an antique worthy of Mrs. Kim’s and bring home a chair that would meet Emily Gilmore's approval.

CUE THE LA-LA-LAS: Click here for antiquing in Cortland County

A road trip this good deserves more than a shuffled playlist. Check the calendars at the Center for the Arts of Homer or Rose Hall, where live music fills these beautifully restored historic churches, each in the heart of town. Catch a show, discover a new favorite artist and give your fall weekend a soundtrack Lane Kim would actually respect. Hep Alien T shirt optional.

Gilmore Bucket List: Catch a live show Lane would approve of.

CUE THE LA-LA-LAS: Click here for upcoming concerts and events

Friday night dinner was sacrosanct in the Gilmore household, and it always started with drinks.

Head to Heuga’s Alpine for seasonal fall cocktails in a stunning setting even Emily could appreciate. Settle in beside the outdoor fireplaces, order an autumnal cocktail and enjoy a crisp evening with star-lit mountain views in an atmosphere that feels just elevated enough for Friday night plans.

Gilmore Bucket List: Never miss Friday night drinks.

CUE THE LA-LA-LAS: Click here to visit Heuga’s Alpine 

Eventually, even the most perfect fall weekend has to end. But there is no rule saying you have to take the fastest route home.

Pick a backroad. Turn up the playlist. Watch the hills turn red, orange and gold outside the windows. Stop when the view demands it. Indulge in just more coffee for the road.

Maybe Cortland County isn’t Stars Hollow. But when the coffee is hot, the bookstores are cozy, the cider doughnuts are fresh, it can feel pretty darn close.

And sometimes the best part of a fall getaway is having your favorite person in the passenger seat and nowhere you need to be quite yet.

So grab the Lorelai to your Rory, take the long way and make a little fall magic of your own.

Build your own Gilmore Girls worthy getaway. Click here to map your Gilmore Inanity with the Experience Cortland Trip Planner. 

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