Every fall, Gilmore Girls fans take over social media with one shared obsession: the show becomes their *entire* personality. Whether it’s re-watching the series in September or immersing themselves in the Gilmorecore aesthetic—complete with coffee, autumn activities, and curling up with a good book—they’re all about living like a Gilmore Girl and recreating the cozy, fall atmosphere of Stars Hollow.
If your feed is filled with posts of the show’s charming autumnal backdrop, here are 10 ways you can experience Toronto as if you were in Stars Hollow this fall.
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Take a Stroll Through the Real-Life Stars Hollow, Where the Gilmore Girls Pilot was Filmed
Imagine you’re Lorelai Gilmore, wandering the charming streets of Stars Hollow in search of your favourite coffee spot—except you’re actually in Unionville, Ontario, less than an hour away from Toronto, where the first episode of Gilmore Girls was filmed. With Main Street lined with quaint coffee shops, grab a hot drink and explore the filming locations on a self-guided tour of everyone’s favourite fictional town. Here are some highlights:
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According to Destination Markham, the “Welcome to Stars Hollow” sign is actually the Unionville Planing Mill sign, located at 139 Main Street. If you look closely in the pilot episode, you can spot the words “Unionville Planing Mill” peeking out from under some decorative leaves.
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The original shooting location for Luke’s Diner at 156 Main Street, which is now a medical spa.
Photo by Christina Armanious
You can also sit inside the festively decorated gazebo, reminiscent of the town square gazebo in Stars Hollow, and admire the charming homes along Main Street, which bear a striking resemblance to Lorelai’s house.
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Visit Richard and Emily Gilmore’s Mansion
While you may not be transported to Stars Hollow, you’ll feel as though you’ve stepped right into Hartford. The iconic mansion from Gilmore Girls, where those eventful Friday night dinners were filmed, is a real property! Located at 61 Binscarth Road, in one of Toronto’s most upscale neighbourhoods, this mansion served as the exterior of Richard and Emily’s home in the pilot episode. So, put on your cutest fall outfit and snap some photos in front of this famous spot.
Immerse Yourself in the Small-Town Charm of Roncesvalles and Catch a Film at a Vintage Cinema
Known to locals as Roncy, this charming neighbourhood exudes the same small-town appeal as Stars Hollow. Perfect for a day trip, it’s brimming with local shops, markets, cafés, and restaurants. A standout gem is She Said Boom!— a used book and record store that’s the ultimate spot to visit with the Rory to your Lane. Whether you’re hunting for titles needed to tackle the “Rory Gilmore Reading Challenge“(500 books mentioned in the show, and yes, people are actually reading them) or rocking out and collecting records from your favourite bands in true Lane Kim fashion, it’s a must-visit.
Roncesvalles is also home to the Revue Cinema, a vintage heritage site where you can catch classic films, much like the Gilmores do at their favourite Black-White-Read Bookstore turned movie theatre. It’s the ideal spot to watch one of the many films mentioned throughout the series.
Join a Basket Draw and Enjoy a Picnic at the Trinity Bellwoods Farmers’ Market
There’s nothing like the town of Stars Hollow coming together for the annual picnic basket auction. In case you need a refresher, rewatch the iconic Gilmore Girls episode (Season 2, Episode 13), A-Tisket, A-Tasket, where the seemingly uneventful picnic basket bid suddenly becomes… eventful. You can experience your own community basket draw at the Trinity Bellwoods Farmers’ Market, where you’ll find fresh, local, and sustainable produce (Jackson would definitely approve), along with autumnal treats like pumpkin pie, honeycrisp apples, and baked sweet potatoes. Open every Tuesday until October 29, the market offers a chance to win baskets filled with goodies donated by local vendors. Afterward, enjoy a picnic in the scenic Trinity Bellwoods Park.
Study in a Dark Academia Campus Library, Just Like Rory at Yale
Opened in 1915, the Caven Library at Knox College (59 St George St) is arguably one of the most stunning libraries in Toronto, perfectly embodying the Dark Academia aesthetic. The campus’ Gothic architecture—featuring pointed arches, ribbed vaults, dramatic stained glass windows, and grand staircases (so picturesque they’ve become a popular backdrop for wedding photos)—echoes the grandeur of the Yale campus where Rory studied. If you love the back-to-school season and are a fan of the later Gilmore Girls episodes, when Rory enters her scholarly era (minus that one not-so-minor hiccup we won’t mention, IYKYK), the Caven Library is calling your name. It’s open to the public from 8:30 AM to 4:30 PM every day.
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Grab a Bite at One of Toronto’s Oldest Diners
While Downtown Toronto may seem worlds away from Stars Hollow, it boasts plenty of charming spots that will make any Gilmore Girls fan feel right at home. One such gem is The George Street Diner (129 George St), a beloved part of the city’s history for more than 80 years and Toronto’s very own version of a trusted local diner. Serving up classic Irish breakfasts and comfort foods, this spot’s unmistakable cozy charm—complete with its red brick exterior, plush red booths, and vintage appeal—makes it a local favourite that feels like Toronto’s answer to Luke’s Diner.
Stay at a Charming Local B&B
Just like Rory and Lorelai’s spontaneous stay at the Cheshire Cat B&B before their memorable road trip to Harvard, you can experience that same charm at By The Park Bed and Breakfast (92 Indian Grove). This century-old, family-run gem features dark woodwork, vintage furniture, leaded glass windows, cozy fireplaces, and beautiful gardens. With delicious home-cooked breakfasts and bottomless coffee, it offers the warmth and hospitality reminiscent of the Dragonfly Inn. Its proximity to High Park enhances the idyllic, peaceful atmosphere, similar to the Inn’s quaint surroundings.
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Celebrate Thanksgiving at the Distillery District Fall Market
Just like the beloved Autumn Festival in Stars Hollow, you can join in on Toronto’s own fall festivities at the annual Distillery District Fall Market. Over Thanksgiving weekend, the historic 19th-century neighbourhood will be adorned with pumpkins and hay bales, showcasing unique and artisanal products from local vendors.
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Savour Fall-Inspired Coffee Flights
If you were to describe Gilmore Girls in a single sentence, it might go something like this: a coffee-obsessed mother-daughter duo in a small town. Just like Lorelai’s constant craving for “coffee, coffee, coffee,” you can channel that same enthusiasm by taking some friends to Your Common Ground (1397 York Rd) for fall-themed coffee flights. It’s the perfect way to enjoy a variety of coffee drinks at once in a judgment-free zone. Rory and Lorelai would be so proud.
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Go Antique Shopping
Kim’s Antiques, one of Stars Hollow’s prominent businesses, located in the Kim household, is renowned for its eclectic mix, narrow aisles, and strict “you break, you buy” policy. While we can’t promise you’ll become best friends with the owner’s daughter or find a secret disco ball and hidden CDs in the upstairs floorboards, Toronto has plenty of charming antique shops that capture the Kim’s Antiques vibe. One standout is Greens Antiques (529 Parliament Street), a family-run shop in the heart of Cabbagetown. With its warm, welcoming atmosphere, it offers a homey experience reminiscent of Kim’s Antiques—though with much more emphasis on the ‘welcoming’ part.
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