Finding Whimsy and Maple Lattes on the ‘Gilmore Girls’ Coffee Crawl

There are certain rituals we cling to as fall sets in: unseasonable sweaters in 80-degree heat. Pumpkin spice lattes. Rewatching Gilmore Girls. After being partially introduced to the show by friends at various points, I’m currently in the throes of my first start-to-finish Gilmore watch. It’s the perfect time for it too, because this month, coffee shops around Nashville are pulling out all the autumnal stops for the Gilmore Girls Coffee Crawl.

Hosted by Prickly Pear Coffee Company, this year’s iteration of the crawl, its second, comes with a big event to match: A full Gilmore Girls takeover of their Gulch location from Oct. 30 to Nov. 1, complete with appearances from Scott Patterson, the actor who plays Luke Danes on the show. In the meantime, participating shops are offering themed specials for the month of October — I still think fondly of Fido’s “Friday Night Dinner” elderflower latte from 2025.

The Gilmore Girls Coffee Crawl is less about the drink specials, though, and more about the adorable activities you do at each stop, which are organized into character-themed columns. As a bookish brunette journalist, I figured I had the best shot of filling out the “Rory Gilmore” column, so I embarked on a journey of reading and journaling at various local cafes. We can’t all consume Lorelai Gilmore’s absurd quantities of coffee, so I gave myself a week of coffee stops. I began as a jaded participant going through the motions — but eventually, I grew to love the time and space the crawl offered me to try new spots and romanticize my routine.

Stop 1: Prickly Pear Coffee Co.

Unlike, say, the Summer Rollout Pastry Crawl, in which participants can pick up a bingo card at any participating storefront, Gilmore Girls Coffee Crawl cards must be picked up at one of Prickly Pear’s three locations. They’re all a bit out of my way and they all close at 2:30 p.m., which made for a somewhat inconvenient start. Prickly Pear’s special is called “The Jess,” though, so it makes sense that it would be hard to get hold of.

+5

Spend a Morning on the Summer Roll Out Bakery Crawl

Audience editor Annie Parnell charts a course through June’s limited-time local bakery offerings

With my card in hand, I started the crawl by asking my barista for a book recommendation (Allen Levi’s Theo of Golden) and settled in for my drink. The Jess is a latte with vanilla, cinnamon and maple syrup, and Prickly Pear describes it as “dark, moody and a little sweet — just like your favorite literary bad boy.” I would have expected something broodier and a little more pretentious for Jess Mariano: a flat white, or maybe a cortado. It’s a solid latte, though, with a warm, nuanced taste despite the sweet flavor profile I was expecting.

Stop 2: Middle Grounds

When I stepped into the living-room-style ambiance of Middle Grounds, the baristas were playing Joy Division and The Brian Jonestown Massacre over the speakers. It was my first time at the Five Points coffee shop, and I felt right at home. 

Their coffee crawl offering, a brown butter maple pumpkin latte, isn’t tied to a specific character, but it does feel very Stars Hollow. There are definitely a lot of flavors happening in this latte, and sometimes they compete a bit. But the pumpkin lends a freshness to a flavor combination that could otherwise lean heavy, giving the special a kind of balanced coziness.

Stop 3: 8th and Roast

I painstakingly selected the tote bag that I brought to 8th and Roast to check off “bring a tote bag.” I ended up going with a light-blue Indigo Girls tote that I picked up at their recent Ryman show — a different “girl” duo that still somehow felt fitting.

Instead of a specific drink, my barista suggested I try any of the drinks on the shop’s fall seasonal menu, which won me a bonus stamp in the Sookie category. I opted for the most Gilmore-ish drink I could find: The Denim Jacket, which is apparently also their most popular fall offering. It’s a latte with caramelized maple syrup, fall spices and maple sugar, and that caramelization brings in subtle layers of flavor.

Stop 4: Stay Golden

I found a new favorite at Stay Golden, the Nations coffee shop and brunch spot that I checked out with my partner Levi on a rainy Saturday. We were on a mission to mark off “read for 30 minutes at a coffee shop,” so I packed Clarice Lispector’s The Passion According to G.H., and Levi brought along Jonathan Safran Foer’s Eating Animals.

Stay Golden’s offering, a drink called For Emily, is inspired by the one and only Emily Gilmore. As they rang me up, one of the baristas on shift declared her the best character in the show — and I can’t blame them. A mocha with red wine grenadine syrup, the drink is an inspired choice. Red wine is a truly underappreciated fall flavor, and its elevated, striking palate tempers a hint of bitterness with chocolate. Delicious — and very true to everyone’s favorite love-to-hate matriarch.

Stop 5: Sol & Luna

Sol & Luna, a witchy green coffee trailer parked near Shelby Bottoms, takes the cake for best vibes of the shops I sampled on this crawl. It’s bedecked in trailing vines and fairy art, with a Practical Magic-themed latte on its regular menu. A vintage clothing sale rack and an art print pop-up complete the whimsigoth ambiance.

Critic's Pick — Impractical Magic Pop-Up

Through Oct. 31 at Hidden Bar at Noelle

Their drink special for the month is Sookie’s Hazelnut Brioche Latte, a latte with brown butter and hazelnut syrup topped with maple cream. It’s a rich, nutty drink that was perfect for the cloudy Sunday afternoon I spent checking off “journal while you enjoy your coffee” on the Sol & Luna patio. As I wrote, I overheard a customer behind me saying “I just love filling my mom in on everything” — peak Gilmore Girls.

It was around this time, though, that I realized that four out of the five coffee specials I had tried for this crawl had maple in them. Now, I love maple. It beats pumpkin any day in my book. With its New England ties, it’s personally nostalgic for me, and it works well for a Gilmore Girls theme. But I wanted a little more variety to feel like I’d fully experienced the crawl. I’d also heard rumors that 8th and Roast did have a character-themed offering after all: A pink drink, named for a certain clandestine lunch date. I had to investigate.

Stop 6: 8th and Roast (again)

Mystery solved: 8th and Roast’s official specialty offering is the Pennilyn Latte, a riff on their typical fall seasonal drink, the Violet Moon. It’s named for Emily Gilmore’s nemesis, Pennilyn Lott, and it’s a latte with flavors of fig, blackberry, vanilla and sage. For a monthlong special offering, I wanted to see more differentiation from an existing menu item — but the cleverness of this drink’s name is undeniable.

I was worried that the combination of all the Pennilyn’s flavor notes would be overwhelming. The blackberry adds the perfect amount of tartness, though, and the earthy fig and sage gives it a subtle savor. Plus, my return trip won me a bonus stamp in the Luke column, for “come back to the same coffee shop during the crawl.” Another plus side of this coffee crawl — it’s a great way to incentivize finding a new go-to.