How to Have a Gilmore Girls Inspired Fall Day

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In my world, fall is synonymous with Gilmore Girls. In fact, my official kickoff to the fall season starts on September 1 with the pilot episode. Every year, I restart Gilmore Girls as I sip apple cider and munch on a pumpkin treat (usually a pumpkin whoopie pie) and pine through my fall magazines. It is pure bliss and it’s even better when I’m home in my small hometown. Let’s be real: fall is just better in a small town. There are so many reasons to love fall, including delicious food and beverages, beautiful fall foliage, lots of festivals and farm activities, vibey books, cozy shows and movies, and boots and sweaters. Gilmore Girls features all of these things and I can’t get enough!

Since I have now watched Gilmore Girls ten times, I call myself somewhat an expert in Gilmore Girl-ology. So, I thought it would be fun to take you through a Gilmore Girls inspired fall day with activities perfectly fit for Lorelai and Rory. Grab your moo-moo sweaters, coffee mugs, books, and donuts and let’s go!

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Table of Contents

Have some coffee at home. (Big gulps, lots of sugar)

First on our list of activities for our Gilmore Girls inspired fall day is to have some coffee at home. You can’t have the Gilmore Girls without coffee. It’s just not possible! Coffee at home is such a great way to start your Gilmore Girls day because you can make it anyway you want to. And we all know Lorelai’s coffee preference: Strong, very, very strong. However, you don’t have to drink it as strong as Lorelai does. I definitely don’t. I love to make fun coffee creamers and put my coffee in beautiful mugs. I think it’s better if your mugs are eclectic and don’t match. It adds to the Gilmore Girls charm. Check out some fun options to add to your home coffee collection.

Coffee Mugs

Coffee

Accessories

Put on a cozy outfit, retro vibes optional.

After you’re done drinking your morning coffee, it’s time to get dressed before heading out the door. Gilmore Girls is known for its coziness, especially during fall. The fall outfits enhance this feeling. You see Lorelai and Rory donning oversized sweaters, boots, earth tones, plaid, and even plain long-sleeve shirts. While some of the fashions are outdated and from 25 years ago (How is that even possible!?), so many women are taking inspiration from Gilmore Girls and creating Lorelai and Rory inspired outfits. Check out some fun pieces you may want to consider adding to your own closet.

Walk through a charming small town.

A Gilmore Girls inspired fall day just isn’t complete without walking around a charming small town. Small towns are known for their adorable storefronts, usually complete with lights and decorations around town, which creates a sense of charm and awe. Small towns are also charming due to the people who live there. They are usually filled with colorful characters, and because the population is typically lower, most people know the shop owners and residents. Check out some adorable small towns worth visiting in the fall. Since Gilmore Girls is based in Connecticut, these towns are all located in Eastern United States.

Take in the autumnal vibes under fall foliage.

You can’t have a Gilmore Girls inspired fall day without basking in fall foliage. In my opinion, there is no better place on Earth to see fall foliage than in the Eastern US. The colors are just stunning. There are very few places where you can see a multitude of reds, yellows, and oranges all mixed together. It’s even better if you get fall foliage while walking through a historic small town. There’s nothing quite like walking down cobblestone streets as your feet trample on colorful maple and oak leaves. Check out this fall foliage map for an interactive peak at when color comes to each state!

Visit a cute book store.

Upon entering your nearest adorable small town, it’s time to find a local bookstore and browse the shelves. Any Gilmore Girls inspired fall day is going to involve books in some way. Stars Hollow Books might not be a real book store, but there are plenty of quaint book stores to give you Gilmore Girls vibes. Most small towns have book stores with lots of charm. I’m biased towards Pennsylvania since I’m a native, so I’m going to shout out two of my favorite book stores in PA. In Wellsboro, From My Shelf Books offers thousands of new and used books. The employees make fantastic recommendations and seeing Huck and Finn, the owners’ two kitties, is an added bonus. In my hometown of Elizabethtown, Bookshelf Shenanigans opened last year. I think it’s one of the prettiest book stores I’ve ever been in. The store offers a great selection of books from all genres and their Dr. Seuss themed children’s area is seriously adorable.

Do some local shopping.

What is walking through a small town without going shopping? Rory and Lorelai love shopping, so it makes sense that this needs to be a part of your Gilmore Girls inspired fall day. Small towns boast a wide variety of niche mom and pop stores that include everything from candles and home goods to candy, decorations, and furniture. Shopping at these small businesses versus a big box store is important because it supports small business owners, keeps money away from huge corporations, and stimulates the local economy. Those who live in small towns rely heavily on the economy of local communities. Consider stopping into a small town and shopping locally before heading to Target or Wal-Mart.

Visit a thrift store or antique shop.

While shopping locally and supporting small business owners, make sure to also check out a thrift store or antique shop. It’s a great way to pay homage to the Kim family who owned the local antique shop in Stars Hollow. While you can sometimes find gems in these stores, it can also feel overwhelming because of the sheer amount of stuff you will find. A tip for you is to make a master list of items you are looking for and to take it with you when you go to a thrift store or antique shop. That way, you can have tunnel vision to only look for what’s on your list.

Visit a town festival.

When you are in a small town during the fall, it’s not guaranteed there will be a town festival, but it is pretty likely, especially if you go during a weekend. There is something so special about a small town festival that just can’t be replicated in a suburban or urban area. In Gilmore Girls, we see town festivals taking place in the town square with the gazebo at the center of activities. Not all towns have a beautiful town square with a charming gazebo, but many contain beautiful main streets with decorated storefronts. Some fall festivals worth checking out include the Morton Pumpkin Festival, National Apple Harvest Festival in Biglerville, PA, Ogonquitfest in Ogonquit, ME, The Great Jack o’ Lantern Blaze in Sleepy Hollow, NY, and AppleFest at Wachusett Mountain in MA.

Have lunch at a diner. Donuts are a must but hold the grapefruit.

At this point in the day, you are probably getting pretty hungry, so it’s time to stop for lunch. In Gilmore Girls fashion, it’s recommend that you find a diner, preferably one with a grumpy owner who wears plaid and a backwards baseball cap on the regular. For some serious diner charm, check out the Wellsboro Diner in Wellsboro, PA, as well as Dottie’s Diner in Woodbury, CT. Both of these diners offer a menu fit for the Gilmore Girls, featuring delicious soups, sandwiches, and homecooked comfort meals. If you can’t find a diner, simply try a local café. I highly recommend Tomato Pie Café in Lititz, PA.

Get some more coffee at a local coffee shop.

One of the many charming factors of small towns is local coffee shops. They are like a mecca for coffee drinkers. You don’t just pay for the drink, you also pay for the experience. Going to a local coffee shop is an experience all on its own. They range from quirky to stunning and sometimes will have board games you can play or even a book store attached. Make sure you stop into a local coffee shop on September 29, which is National Coffee Shop Day. My favorite coffee shop of all time is New Holland Coffee Co. Not only is their coffee shop absolutely gorgeous and so aesthetic, but their coffee drinks and food are top notch. Other shops worth visiting include Nickel & Bean in Lexington, OH, Kairos Coffee House in Colorado Springs, CO, White Magnolia Coffee Co. in Myerstown, PA, and Mean Cup in Lancaster, PA.

Spend time reading a book, preferably under a tree.

After all of your hard work on this Gilmore Girls inspired fall day, it’s time to relax and crack open that book you just bought. Whether you read in the adorable coffee shop you found or head to the local park, get cozy and have fun reading. If you want to be even more in Gilmore Girls fashion with your reading, find a perfect reading tree to sit under as you watch the leaves fall gently to the ground. Extra points if you wear a black turtleneck sweater and Army green corduroy pants.

Eat a Lorelai approved dinner.

A Lorelai approved dinner includes not cooking. This means you will be putting tater tots on a baking sheet, ordering tacos from a drive-thru, getting pizza or some kind of takeout, or eating someplace where healthy options are not a top priority. Either way, you have burned many calories today doing all of that walking, shopping, and reading, so feel free to indulge in whatever way suits you. If you do feel like cooking, consider making a recipe featured in the Eating Gilmore food blog or one from the Official Gilmore Girls Cookbook.

Watch a movie and include some Gilmore Girls inspired treats.

Last on the list for our Gilmore Girls inspired fall day is to watch a movie and eat some delicious treats. To make this a fall activity, we’ve got to watch a fall movie and eat some fall treats. Below, check out some movie suggestions and delicious treats that Lorelai and Rory would absolutely approve of.

Fall Treats

Movies

You’ve Got Mail
When Harry Met Sally
Dead Poets Society
Twilight
Harry Potter and the Sorcerer’s Stone
Good Will Hunting
Matilda
October Kiss
Practical Magic
Halloweentown
The Princess Bride
Psycho
The Trouble with Harry

I hope this post has inspired you to have your own Gilmore Girls inspired fall day! It should include lots of fall fun and small town charm. Whatever you choose to do during your day, make sure it’s something that brings you lots of joy as we usher in the coziness of the fall season. Until next time, Kayla.