Why the 'Gilmore Girls' Fan Festival Is the Ultimate Friends Weekend Getaway

Say it with us now: 'Where you lead, I will follow.'

gilmore girls fan festival
Courtesy of Elisa Benson

"There are many paths in life ... The thing with my path was, when I reached the end, I turned around and realized I'd ended up someplace really good." —Lorelai Gilmore

The first year of the , I showed up in a prep-school uniform modeled after Rory Gilmore's. It was my friend Elisa's idea; she was going with me and she's charming enough to get me to do things like dress up as the teenage protagonist of a WB dramedy, despite being a mom in my 30s and despite the fact that the show has been off the air for nearly 10 years.

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Turned out, we were the only attendees who dressed up as our favorite Stars Hollow eccentrics that year, but the inaugural event was so much fun that I've since returned with Elisa — in regular clothes — for the past two years. This year, I was even invited by festival organizer and Gilmore Girls superfan Jennie Whitaker to host a couple of events on the kickoff day of the festival.

When we talked about coming back to the fan festival, we decided that we'd use Saturday and Sunday to do some New England exploring. We had a wide-ranging list that started with Niagara Falls and ended with Yale, none of it based on any sort of research or reality. And we've both been so busy with work and life in general, neither of us managed to actually plan anything. I'm normally a super detail-oriented planner, so it makes me nervous not to know what's next, but it looks like winging it is the only thing on the agenda.

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Hitting the road

Back in 2016, Jeep was kind enough to loan me a Wrangler just like Lorelai Gilmore drove throughout the series' seven-season run. (I was really intent on going all-in with my fandom.) This time, I opted to borrow a , which is really fun to drive — with the added bonus of having, like, windows you don't have to zip closed.

The drive up from my New Jersey town through rural Connecticut is absolutely breathtaking. The Cherokee immediately recognizes my phone when I plug it in so I can make calls through the interior mic system. (This isn't brand-new technology, but it's the first time it's worked seamlessly for me — and that's revolutionary.) Since Elisa is meeting me in Connecticut later and I'm alone in the car, catching up with a friend on the phone makes the drive go by much quicker.

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The 2018 Jeep Cherokee Limited.
Annemarie Conte

I arrive at the main festival tent in Kent, Connecticut, just in time to run my first event, a Newlywed Game-style quiz where people have to guess what their BFF would say. It goes swimmingly, I get to give out some awesome prizes ( gift cards! A Google Home Mini! A cool print of the Milford, Connecticut gazebo done by a local artist and Fan Fest volunteer), and I'm immediately reminded why I love other GG fans. They are all so stinking nice. Last year, a police officer told me in wonder that he'd never seen a festival of such size run without incident or even tons of garbage. Gilmore Girls fans are not a rowdy bunch. The festival photographer snaps a photo of me looking like a lounge singer.

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I’m a crooner.
Chela Crinnion
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I wish I had more time to linger, but I still have a ton of prep work for the evening's panel. I slip away and check into the , run by innkeeper Peter Starbuck. We chat about small-town life, and then I have to head out to pick up Elisa, who's taken the 2.5-hour train ride from NYC. We go straight to the panel discussion, where I learn all about how TV writers, costumers, dialogue coaches, and producers got their start in the business. It's completely fascinating, and I love hearing about jobs the rest of us never knew existed!

By the time it's over, I'm famished, so Elisa and I run across the street to the , where we consume huge plates of short ribs and cocktails with fall names like Pumpkin Run. Then we retire back to the Starbuck, where Peter has left out sherry as a digestif. Elisa suggests we jump into our bathrobes and have a glass, because that seems like the type of thing one does a Connecticut country inn. It turns out we really don't like sherry, but does that even matter?

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The lovely dining room at the Starbuck Inn.
Annemarie Conte

The next morning, Peter serves us frittatas for breakfast in his stunning dining room and then Elisa and I wander back down the main street to check out the other cute establishments like and (apparently, we like shopping for liquids). I donate a few dollars to a local kid's Eagle Scout project before we head back to the main festival tent to watch a costume contest. (Now there's costumes!) Hundreds of women (and a few men! and a baby!) are prancing across the stage in funny, clever, and freakishly accurate getups that are definitely better designed and thought-out than Elisa and I ever put together. I am overwhelmed by the sheer power of fandom and all of the fun, cool connections that are going on throughout the weekend and I start to tear up. No one thinks it's weird. I am with my people.

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Where you lead, I will follow

We have a lunch date with a friend, so our time in Kent is drawing to a close. We still don't have a plan, and internet service can be spotty in these parts, so we figure we'll do it the old-fashioned way and actually (gasp!) talk to people. Worst-case scenario is that we drive back to Jersey or sleep in the car if we can't find a hotel with vacancy (the car does have a giant sunroof, so maybe it would be like camping?). When our friend asks us where we're off to next, we shrug and say we're trying to figure it out. "Oh, you should go to Lenox, Mass. It's cute. You'll like it," he says succinctly. Sounds good to us. We don't need more detail than that!

The drive is about 75 minutes long, but 20 minutes before we arrive in Lenox, Elisa needs a cup of coffee, so we stop at a cute cafe called in the adorable town of Great Barrington. As Elisa picks up her pumpkin spice latte, we spy a poster for a Hocus Pocus-themed drag show taped to the cash register. The barista tells us there aren't any tickets left, but we can come back and try for standing-room-only space. We file it away for later and continue on to Lenox.

Deals! Deals! Deals!

Turns out, Lenox is even more adorable than Great Barrington. But we only get to see about five minutes of it. I buy a postcard in a bookstore named (New Englanders don't do flowery) and as we are about to explore further, it starts to rain. I serendipitously get a text from my friend, Katy Lukens, who lives about an hour north and invites us to stay the night. Hooray, no car camping! She also mentions that there's an outlet store about 20 minutes away and if we hurry, we can get there before it closes. Annie Selke is an interior designer known for her "global chic" aesthetic. I don't know if I also have a global chic aesthetic, but I definitely have an "I got this for 75% off aesthetic" so I hit the gas and we get there in record time.

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Katy instructs us to head straight for the clearance room, which we do, scoring a $10 gold-embellished blanket and some patterned throw pillows. I waffle on an $85 pouf (because I'm still not completely sure what one does with a pouf), and ultimately can't justify it. But I do buy a $50 comforter that has the world's most imperceptible stain on it (the saleswoman nicely lays it out on a bed for me and has to point to it for a full minute while I squint and desperately try to see what she's seeing). "You should come back for the tent sale in July," Katy advises us later. "The deals are crazy." I'm not the type to throw elbows to get my hands on an $1,100 bar cart (even if it’s 75,000% off), so I'll leave that to the hardcore Annie Selke fans.

It's just a bunch of hocus pocus

With the trunk of the car loaded up with soft goods, we head back to Great Barrington to talk our way into the drag show. It's a 6 p.m. seating for dinner and the performance. The crowd arrives promptly at 6 and seems to hold a fairly high concentration of people over the age of 65. The organizers take pity on us and pull an extra table over and scrounge up two chairs. We are so excited to see the roles made famous by Bette Midler, Kathy Najimy, and Sarah Jessica Parker come to life in front of us. And I will say this: the costumes are amazing. But, sadly, the whole thing seems under-rehearsed, so we slip out after the first set.

The next morning, we wake up at Katy's house in Northampton, and she offers to take us to a few of her favorite spots in the area. She's the features editor of the Daily Hampshire Gazette who just put together a list of , so if she doesn't know what's up, no one does.

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Florence Pie Bar, filled with delicious pies.
Annemarie Conte

Elisa is on a mission to have pie for breakfast (it's her family tradition, and frankly, one that I think everyone should adopt) so our first stop is , a perfectly Instagrammable bakery with indoor and outdoor seating, complete with twinkle lights, naturally. It's nearly impossible to choose, but they let you taste samples (it's like an ice cream shop decided to sell pie instead!). We land on apple pie with cardamon, salted maple pie, and a blueberry crisp, which we consume with reckless abandon. We then make our way to , a discount store packed to the brim with everything from Sketchers footwear to Bob's Red Mill flours to Burt's Bees beauty products. I buy two bags of tapioca flour (because doesn't everyone need two bags of tapioca flour?) and will be making until my family cries for mercy.

The final leg

We don't have time for some other great spots Katy recommends because we have to get to in Charlton, Massachusetts, before they close. The beer I buy from there will serve as a salvo to my husband, who's spent all weekend with our two young girls and has not once sent me a "come home immediately, our children are wild jackals" text. The brewery very strictly controls the quantity and type of beer you can buy, but the staff is super-nice, despite it feeling a little bit like being sent to the principal's office. I buy the maximum and have to haul it out with a hand truck.

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It's mid-afternoon and we are starving (turns out pie for breakfast doesn't hold you all day!) and no food is served at the brewery so we ask the bartender for the last recommendation of our trip. She sends us 6 miles down the road to a gas-station-adjacent restaurant in Sturbridge, Massachusetts, that I would have driven right past if I wasn't told it was there. We cram ourselves full of fall-off-the-bone barbecue, and I can only imagine how packed the place gets during the huge , which draws crowds of thousands come summer.

To be honest, we may have had just as much fun if we'd planned the trip ahead of time, but this gave us a follow-your-gut-and-see-where-it-leads-us sense of adventure that never happens in our overscheduled daily lives. And we can't wait to do it again next year.

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