Guess Where we’re going?

What follows is a glimpse into the kinds of discoveries you might encounter, drawn from three different Guess Where trips we’ve taken recently (of the more than 100 trips the company offers). Each one has its own unique blend of charm, curiosity and unexpected delight. In true Guess Where fashion, we didn’t know what was coming next, and that was part of the fun.

With each sealed envelope, new adventures unfolded: tucked-away cafés where the espresso was as memorable as the view, family-run shops filled with stories and handmade treasures, scenic hikes hidden just off familiar highways, national historical sites, and even a family-owned artisanal cheese shop offering traditional Dutch methods and more than twenty varieties of Gouda. Despite having lived in this region for years, we found ourselves uncovering corners of our own backyard we never knew existed, reminders that discovery doesn’t always mean crossing an ocean. Sometimes it just means taking a new road close to home.

For us, the experience was made even better by the 2026 Platinum Elite Acura MDX from Acura West London we took along for the ride. It wasn’t just a vehicle, it felt like part of the adventure. This vehicle could easily hold seven passengers, and the spacious cargo area easily fit our cooler, bags and the quirky finds we picked up along the way. The Google Built-In navigation kept us on track without fuss, and the Bang & Olufsen sound system gave the Guess Where curated playlists a cinematic feel that matched the mood of each stop.

Driving the MDX felt effortless. It was quiet, smooth, and responsive, especially along winding backroads and those spontaneous detours that make these trips so memorable. The leather massaging seats, panoramic sunroof, and Head-Up Display added a layer of comfort and safety that we genuinely appreciated. And the large touchscreen made it easy to stay connected and adjust plans on the fly, which fit perfectly with the flexible, go-with-the-flow nature of a Guess Where Trip.

Guess Where?

When Jessica Off dreamed up the idea for Guess Where Trips in London, Ontario, it wasn’t born in a boardroom or backed by a big investor pitch. It started with something far simpler: her love of discovering hidden gems. “I’ve always loved the idea of discovering off-the-beaten-path places,” she recalls, “but I found that planning road trips often took away from the fun and spontaneity. I wanted to create something that made exploring easier, more surprising, and more memorable … while supporting local businesses along the way.”

In 2020, armed with nothing more than an $80 printer and a handful of hand-crafted itineraries, Off turned her vision into reality. Today, Guess Where Trips has blossomed into a thriving business with adventures across Canada and the United States. What began as a small project to spark joy during the uncertain times of the pandemic has become a movement, encouraging people to rediscover the extraordinary in the everyday and reconnect with the spirit of exploration.

Off went on to appear on Dragon’s Den where she earned enthusiastic financial support to grow her business.

Starting Our Mystery Road Trips

Our journey began with a sense of adventure and curiosity as we wound our way through the scenic back roads of Perth and Brant counties, eventually reaching the vibrant regions of Stratford, Waterloo and Hamilton. Along the way, we discovered we weren’t alone. There was a whole community of “Guess Where” road-trippers out exploring their own mystery routes.

At one of our early stops, Mountainoak Cheese, we chatted with a friendly couple from Port Elgin who were on their second Guess Where Trip. They had customized their two trips, giving extra time to new stops while omitting some closer to their home. Later in Ayr, we met Kayleigh Kirk at the Willibald Farm Distillery & Brewery. Like others we chatted with, she had received the trip as a Christmas gift and was thrilled with the experience, praising the variety of activities and the helpful timing recommendations. Her advice? “Read the recommendations and pick a nice day to go, ideally a weekday when the stops aren’t as crowded.” Another tip we picked up from fellow travelers: embrace spontaneity and be open to discovering hidden gems beyond the official stops.

Food & Drink

With that spirit in mind, our Guess Where visit to Mountainoak Cheese in New Hamburg led us on a delicious detour, to Stonetown Cheese in St. Mary’s. Mountainoak Cheese is a charming, family-owned dairy farm and cheese producer run by the Van Bergeijk family, who emigrated from Holland in 1996. The farm prides itself on using milk directly from its own cows to craft award-winning gouda cheeses. Guided tours of the cheese plant are available for booking, offering a behind-the-scenes look at the cheese-making process.

We couldn’t resist picking up a few specialties: the rich and earthy Black Truffle cheese, the unique Wild Nettle variety, and a sweet treat, a stroopwaffle ice cream sandwich. As with any road trip, it’s always wise to have a cooler and a picnic basket tucked in the backseat.

Inspired by our cheesy start, we made our impromptu stop at Stonetown Cheese, another on-farm cheese producer known for its Alpine-style offerings. The cheese is made fresh daily using raw milk from cows milked each morning by the father of the family. The operation is led by Swiss Master Cheesemaker Ramon Eberle, a fourth-generation artisan whose expertise shines through in every wheel.

We sampled and purchased the Wildwood, an Appenzeller-style firm cheese that had recently earned the title of Grand Champion at the 2023 SIAL Canada competition. Stonetown has a viewing window into the production room and also offers guided tours, giving visitors a chance to learn about traditional Swiss techniques and the passion behind each product.

One of the charms of a Guess Where Trip is the way each adventure begins. At the start of every itinerary, the guide suggests a hidden gem to ease you into the day, a spot for a leisurely coffee, fresh-baked goods, or a wholesome breakfast.

One particularly memorable stop was the Dog-Eared Café in Paris, Ontario. Owned by Darren Jones and Jeanette Janzen-Jones, this cozy spot has become something of a phenomenon thanks to its inclusion in Guess Where Trips. Inspired by European café traditions, it offers a warm and inviting atmosphere, and shelves lined with over 5,000 used books for purchase. Guests are encouraged to bring their own good quality book donations, which the café accepts in exchange for vouchers toward future purchases. With a lovely view of the Grand River, it’s the kind of place where you could happily linger all morning. We paired buttery pastries with one of their signature espresso drinks, the maple oat latte topped with toasted marshmallows, which turned out to be as whimsical as it was delicious. This café was one of the stops that offer a discount on purchases by showing your Guess Where itinerary. Typically, there are two discounts in every Ontario mystery tour. Watch for those in the guides!

On another trip, we discovered the Ashbourne Café & Bakery in Stratford. Here, talented Chef Buffy Illingworth puts the focus on health-conscious dishes crafted with unique, flavourful ingredients. Alongside a first-rate latte, we enjoyed a protein-rich breakfast that was as beautiful as it was satisfying: smoked salmon on toast with lemon-caper goat cheese, mixed greens, pickled onion and a perfectly poached egg. Another standout was the Turkish Eggs, a poached egg nestled on garlicky yogurt, drizzled with chili butter, and served with toasted charcoal sourdough. We left energized and inspired for the rest of the day.

The Hotel Julie exterior hints at the creative twists inside the reimagined 19th-century inn

On our way out of Stratford, we were wowed by the Wild Hog Market. Family-owned and operated, the year-round indoor market features great to-go sandwiches, huge scones and cookies as well a large variety of gifts, meats and foods. We’re looking forward to returning for one of their long-table dinners and to pick up a brisket for the smoker!

For beer, wine and spirits lovers, watch for tours that specialize in these areas. It’s nice to plan for a brewery stop and one we recommend is Willibald Farm Distillery & Brewery in Ayr. This time of year the Farmtoberfest Lager is a refreshing beverage. They also sell takeaway cans in their retail shop. We were reminded that a great journey isn’t just about where you end up, it’s also about the little indulgences and connections you make along the way.

A Haunted Pub with Character

As the day unfolded, Guess Where Trips kept us well supplied with culinary stops that were as memorable for their atmosphere as for their food. In Ancaster, on a spooky themed tour, we landed at the Coach & Lantern, a classic pub that felt like stepping back in time. With its subdued lighting, weathered stone walls, and fireplace, the space radiated a cozy warmth that immediately drew us in from its hidden back garden entrance.

Spread across two floors, the main level serves as the traditional pub, while the upstairs doubles as an event space, often hosting paranormal evenings that lean into the building’s storied past. Our server, clearly familiar with the pub’s ghostly reputation, shared a tale about a corner table set for three. More than one guest seated there has reported the eerie sensation of being tapped on the shoulder, only to turn and find no one behind them. Ghost stories aside, the menu delivered exactly what you want from a traditional pub: hearty fare, generous portions and reasonable prices.

Accommodations

After a day of winding backroads, hidden cafés and the warm welcome of the vendors along our routes, our last mystery trip had one more delight in store: an overnight stay. Guess Where Trips provides numerous accommodation recommendations for those who want to extend their adventures. Hotel Julie in Stratford was a perfect fit for the spirit of the journey. This boutique retreat combines modern design with the quiet elegance of a heritage building, offering an atmosphere that feels both stylish and deeply restful. Each of the 10 rooms, or flats, has a unique design. In the Serpent Suite, with its balanced crisp, contemporary lines and thoughtful touches that made it feel personal rather than polished for show, we dropped our bags, exhaled and instantly felt at ease. It featured two queen beds, a living room and a full kitchen. It’s a fully digital hotel experience, without a front desk; guests are sent a check-in code via text. Hotel Julie provides parking and is a short 10–15-minute walk to downtown or the Stratford theatres.

Waking refreshed the next morning, we lingered over coffee while sunlight streamed through tall windows, packed up the Acura for another day of discovery and cracked another envelope.

Nature and History Along the Way

Each “Before You Go” package provides helpful tips on clothing and footwear, and for this outing comfortable walking shoes were essential. Our first stop was the FWR Dickson Wilderness Area, part of the Spottiswood Pinehurst Lake Wetlands Complex near Ayr. Here, an old oak forest, thicket swamp and tallgrass prairie come together in a rare mix of ecosystems. We wandered along the boardwalk and nature trail, pausing often to listen to the chorus of birds around us.

A friendly birder pointed out a Pileated Woodpecker, and with the Merlin app in hand, we identified calls from several other species, a moment of discovery that felt both serene and exhilarating.

From there, the day shifted from the natural to the historical. In Baden, we visited Castle Kilbride, the magnificent Victorian mansion built in 1877 by linseed oil magnate James Livingston. Our hosts from the Township of Wilmot welcomed us warmly, sharing stories of the home’s elaborate artwork and its transformation each December for Christmas celebrations. Bedecked with trees, ribbons and garlands, the house becomes a vision of Victorian England at Christmastime, complete with costumed staff guiding self-paced tours. Even in the off-season the sense of grandeur lingered, offering a glimpse into the elegance of another era.

On another mystery tour, we found ourselves in Hamilton at Dundurn Castle, a place I had driven past countless times during my university years but had never truly explored. The Guess Where itinerary pulled us in to experience both its architectural beauty and its darker past. Ghost stories abound here, and while wandering the grounds and taking in the sweeping view of Burlington Bay, it was easy to imagine the echoes of another century lingering in the stone walls.

Final Thoughts

By the end of our journey, it was clear that Guess Where Trips has struck a rare balance: structured enough to feel reliable, yet surprising enough to feel magical. Each stop carried its own story, weaving together local businesses, natural beauty and history in ways that made even familiar places feel brand new. And with the Acura MDX as our trusted companion, the road itself became part of the adventure, its comfort, quiet confidence and easy handling turning the miles between stops into moments of connection and anticipation. In the end, the trip wasn’t just about where we went, it was about the shared sense of discovery, the joy of the unexpected, and the reminder that sometimes the best journeys begin without knowing the destination.

Bruce Fyfe and his companion were guests of Guess Where Tours and Hotel Julie, which did not review or approve this story.