7 charming small towns to visit in Ontario for a ‘Gilmore Girls’-inspired day trip, Canada Reviews

Although Stars Hollow — where Gilmore Girls’ Rory and Lorelai live — is fictitious, the pilot episode was shot in Unionville, Ont., about an hour away from Toronto. There, you can visit Luke’s Diner, read under the gazebo and take pictures with the town of Unionville sign that the Stars Hollow sign was plastered over in the pilot. 

Unionville isn’t the only small town with this idyllic charm in the province. Here are a few more must-visit villages and towns where you can get the Gilmore Girls experience. 

Elora 

Elora is a historical village most known for its limestone gorge and architecture. The picturesque sights, unique shops and cozy accommodations will transport you to Stars Hollow — including locally-owned bookshop Cordial Clove Books with its own dog mascot to greet you at the door and a fascinating antiques and curiosities shop, Mermaid in Elora. Often ranked one of the most beautiful towns in Ontario, Elora is best experienced with a focus on the natural attractions, as well as the downtown area. 

St. Jacobs 

Just outside Waterloo, St. Jacobs is rife with seasonal festivals, artisan wares, organic goods, untouched historical buildings and a huge, three-building farmers market. In Stars Hollow, the Gilmores and clan enjoy a slower pace of life and a closer sense of community. Take a leisurely stroll through St. Jacobs, talking to the friendly locals, to recreate this experience. Catch their Sparkles Holiday Shopping Event Nov. 13–16 and 20–23. 

Downtown Orangeville 

Downtown Orangeville boasts a year-round farmers’ market, festivals, heritage buildings, public art, local shops, dining and a small-town feel just outside the city. Take a self-guided walking tour or hit up one of their events like the Joy & Lights Festival next month. Walking through this picturesque town is especially beautiful in the fall, and with historic buildings lining the streets, a clock tower and trees decorating the sidewalk in fiery colours, you’ll feel like you might turn the corner and run into Sookie or a very grumpy Luke at any moment. 

Kleinburg 

Hidden in plain sight in the City of Vaughan is the village of Kleinburg. Peaceful, quiet and serene, slow down and enjoy some small town living in this pleasant community — get your coffee fix just like Lorelai at the cozy Kleinburg Kafé and pretend you’re gearing up for the Autumn Festival as you take in the sights of the falling leaves and colourful trees. Make the most of your visit by experiencing a part of Canadian history at the McMichael Canadian Art Collection. The art gallery focuses on the work by the Group of Seven painters, who are most known for their beautiful natural landscapes. When the cold weather rolls around, the Kleinburg tree lighting ceremony is the epitome of small town charm — and you can have your own Lorelai moment, celebrating the first snowfall of the season. 

Port Dover

Port Dover is a small lakeside town known for its fishing — its perch and pickerel more specifically. In the Gilmore Girls universe, Stars Hollow is populated by quirky and interesting characters with unique ways and traditions, like their 24-hour dance marathon, so-called Teen Hayride and even a knit-a-thon. In Port Dover, every Friday the 13th, thousands of motorcyclists gather and ride through the small town, bringing excitement and tourism. It’s quite the sight to see and more action than the otherwise sleepy community is used to. Join in on the fun and get a taste of what Rory experienced growing up in a kind of quirky community! 

Gravenhurst 

Gravenhurst, known as both “Sawdust City” (a reference to its logging past), and the “Gateway to Muskoka”, is a beautiful historic town. Visit for the steamship cruises, natural attractions or the blossoming craft beer scene. While Gravenhurst, unlike Stars Hollow, is a lakeside town, its downtown area and main street are dotted with red brick buildings much like the historic ones that make up the Gilmores’ town — including the famous Opera House, worth a visit for its lively calendar of music shows, theatre and comedy. There’s even a coffee shop with some serious Luke’s vibes — aptly named Oliver’s! 

Niagara-on-the-Lake 

Niagara-on-the-Lake is a scenic Southern Ontario town well known for wineries as well as its theatre festival in the summer and rich cultural scene. If you visit in the winter months, the whole town is lit up like the North Pole. The Christmas village feel brings in thousands of tourists a year — and you’ll be transported right into the wintry scene of the Gilmore Girls episode with the Bracebridge dinner, including your very own romantic horse-drawn carriage ride.