Hollywood is obsessed with this Ontario town and I went to find out why

If you've watched the IT films, chances are you've already wandered the streets of Ontario's picturesque Port Hope without even realizing it.

The picturesque Ontario town was transformed into the fictional town of Derry for both the blockbuster IT films and the prequel series IT: Welcome to Derry, with everything from its historic main street to its iconic theatre appearing on screen. It's also popped up in productions like Reacher, The Handmaid's Tale, American Gods and Murdoch Mysteries.

Curious to see what kept drawing Hollywood back, I spent a summer day exploring Port Hope for myself. While the filming history is reason enough to put the town on your summer road trip list, I quickly realized it's worth visiting even if you've never seen a single one of those productions.

I had one advantage over most visitors: Rebecca, one of my closest university friends, grew up in Port Hope and, along with her husband and toddler, was waiting to show me around the places locals actually love.

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Our first stop was The Pulse Café & Eatery, just outside the downtown core. The café's large parking lot makes it an ideal place to leave your car before exploring on foot, while the dog-friendly patio overlooking railway tracks was entertainment for everyone in our group — especially Rebecca's daughter.

The Pulse Café & Eatery. Photo: Hannah Abrahamse

Inside, owner Jessica Hillman welcomed us and told me about the café's focus on sourcing ingredients from local farmers and makers, with everything made fresh in-house. I had the Reuben and an elderberry lemonade.

The Pulse Café & Eatery. Photo: Hannah Abrahamse

The Reuben was hearty and packed with flavour, while the lemonade was bright, refreshing and lightly sweet.

The Pulse Café & Eatery. Photo: Hannah Abrahamse

Before we left, Jessica suggested leaving the car at Pulse, walking up John Street, exploring Walton Street and looping back along the Ganaraska River. It turned out to be the perfect route, and my first glimpse at how open Port Hope locals are to sharing their town with visitors.

As I packed away my gear to start walking, Rebecca laughed. "You really don't have that far to go."

She was right. Port Hope is incredibly walkable. Everything is clustered close together, making it almost impossible to get lost and easy to stumble from one destination to the next.

Within minutes, I was stopping to look at beautifully preserved heritage buildings like the Henry Howard Meredith House and the historic Hotel Carlyle. I love how nothing in Port Hope feels staged for tourists. It's simply a town that has taken care of its history.

We passed the Little Station, where someone was painting dozens of handmade 101 Dalmatians T-shirts for an upcoming parade. She happily paused to explain the project before picking up her paintbrush again. It felt like the kind of thing you only stumble across in a small town where everyone knows what's happening. "There's always something like this going on here," Rebecca laughed.

Before we even reached Walton Street, Port Hope's main street, I was already shopping. We stepped into My Sister's Closet, a consignment shop much bigger than it looks from the outside, and I fell in love with a pink leather jacket that I absolutely didn't need.

I left it behind, but I'm still thinking about that jacket.

Then, on Walton Street, cute, independent shops pulled me in every few doors. At On 2nd Thought Upcycling, owner Carolyn Scatterty showed me jackets made from vintage tapestries and family quilts that had been transformed into wearable art. A few doors down, Rebecca found a pair of Free People shorts at Canoe and Lake while I browsed shelves of quirky gifts, including socks with phrases like "theatre kid." 

I could have easily lost hours browsing the stationery, books and gifts at Bibelot. Their Jellycat selection alone is enough to tempt some collectors into making the drive to Port Hope. Even my dog found her own favourite stop, quickly making friends with their resident shop dog.

My dog also insisted on a stop at Dukes Pet Food, where I loved seeing furry visitors treated like celebrities and shelves stocked with treats and products from smaller Canadian businesses.

Downtown Port Hope has embraced the IT franchise without overdoing it. Many businesses have maps showing where famous scenes were filmed, and some sell IT-themed merchandise. I snapped the obligatory photo in front of the infamous "meat door," walked past Watson's Pharmacy, which became Keene's Pharmacy in IT, and stopped outside the Capitol Theatre, which doubled as Derry's iconic cinema. 

At this point, we needed a snack, and Rebecca said I couldn't leave town without trying Dreamers Café's famous Crazy Cookie. The trademarked chocolate-, caramel- and pecan-filled treat first became popular after the cast and crew of Happy Town discovered it while filming in Port Hope. After one bite, I understood why. By that point, I was convinced Hollywood keeps coming back to film here for the same reasons everyone else does.

Dreamer's Cafe. Photo: Hannah Abrahamse

Before leaving downtown, we ducked into Milly's, a specialty grocery store and cafe that has a gorgeous interior. I left with a few local treats and the feeling that I'd barely scratched the surface of everything Port Hope's small businesses have to offer.

One of Port Hope's best features is definitely the Ganaraska River, which we walked along back toward The Pulse.

Every fall, thousands of salmon make their way upstream during one of Ontario's largest salmon runs, but in the middle of summer, the riverside trail is peaceful, and the gently rushing river is a stunning sight. It's enough to make me want to come back in the fall to see the salmon run for myself.

Rebecca's husband made sure we stopped off along one final IT filming location at Memorial Park, where Pennywise terrorized the Losers Club beneath the towering Paul Bunyan statue. Their toddler, meanwhile, was far more interested in Zac's Dream Park next door—an accessible playground built in memory of local resident Zac Armstrong, where children of all abilities can play together.

Exploring with both my dog and Rebecca's toddler made me realize just how family-friendly Port Hope is. Between the walkable downtown, dog-friendly businesses and plenty of green space, it's the kind of destination that works whether you're travelling solo, with kids or with your dog.

After saying goodbye to Rebecca and her family, I met up with my dad for dinner.

Everyone had told me not to leave Port Hope without trying Olympus Burger. The restaurant has earned national recognition from You Gotta Eat Here!, Canadian Living and Food Network, building a reputation as one of Canada's top burger spots.

Founded by George Kallonakis and his father, Olympus Burger draws inspiration from their Greek heritage. Blue-and-white décor nods to Greece, and every burger is named after a figure from Greek mythology.

Although the restaurant is now under new ownership, the owner told me the 
Greek-inspired theme isn't going anywhere, and neither is the commitment to the quality that earned Olympus Burger its national reputation.

Olympus Burger. Photo: Hannah Abrahamse

He also let me in on Olympus Burger's worst-kept secret: a hidden menu on the restaurant's website featuring bonus burgers and sauces like tzatziki, peanut butter and even Nutella.

My dad and I shared the Olympus Fries, piled high with an undisclosed sauce that is absolutely delicious and tastes like creamy Greek dressing feta, along with a fresh Spartan salad (a traditional Greek salad), both of which exceeded my expectations, before ordering the Zeus and Hades burgers.

Olympus Fries. Photo: Hannah Abrahamse

I also couldn't resist trying a mysterious blue milkshake. I never did find out exactly what was in it, but it tasted like Dunkaroos.

My dad declared his Hades burger one of the best burgers he'd ever had. I can't argue with him.

Before heading home, we made one last stop at East Beach.

East Beach. Photo: Hannah Abrahamse

As the sun dipped over Lake Ontario, it felt like the perfect ending to a day filled with great food, independent shops, beautiful scenery and people who genuinely love where they live.

The filming locations are worth seeing, but what stayed with me most wasn't where Pennywise once stood. It was the people who happily pointed me toward their favourite café, shop or walking trail—and yes, the pink leather jacket I still regret leaving behind.

By the time I merged back onto the highway, I already had a list of places I wanted to revisit.

To me, that's the sign of a great day trip.