The Whimsical Route: a Recount of our Mystery Road Trip.

Editor's note: This post details a recent mystery road trip I took. I will do my best to keep the specifics about the locations and sites secret. This post is not affiliated with the company mentioned. This was a gift, and I am chronicling my experience.

I woke up the morning of July 10th to a text from a friend: “A mysterious package will arrive for you today.” This was not an unusual message to receive from the sender. Given it was my birthday just a week prior, I suppose this was "on time" for her. I thought of the words spoken by Miss Scarlet in the 1985 film Clue: “I love receiving gifts from strange men.” A few hours later, a strange deliveryman appeared at my door with a stark white box. The label affixed did not indicate what was inside. I was on my way to a work lunch, but who would I be to let this box sit in waiting? It was begging to be opened.

Inside, I found a belated birthday gift. While opening the box, I was as giddy as a child at Christmas. I received a mystery road trip from Guess Where Trips. This befuddled me as I had not heard of this company until that day.

Guess Where Trips is an Ontario-based travel company that curates one-day road trips around the provinces of British Columbia, Alberta, Ontario, and Nova Scotia. They also have trips in the United States. 

The package was neatly tucked into a branded tote. The portfolio of information was bound by a string and a handwritten tag that read.

“Happy birthday, Bergsma! Ontario - it’s yours to discover!”

My friend, "Roberts,” knows me well enough to know this would thrill me. She was sending me on “The Whimsical Route” as depicted by the postcard under the string with the note. The curator describes this route as:

“Get ready for a road trip where nature, history, hidden gems, and a touch of cinematic magic come together for a perfectly whimsical escape just outside the city!”

I love this because it gave zero indication as to where I was going. Inside the package are five envelopes - “Before You Go” and the four mystery locations. The beauty of the packaging and its meticulous construction convey a sense of anticipation, as if you are about to embark on a mystical journey. 

The “Before You Go” envelope contains the necessary information for your trip. It reads as a vague instruction guide on how to prepare for your day out. This includes times to leave, your destinations with aptly titled descriptions, what to pack, where to find travel updates, and, if needed, where to stay overnight in the general area you are visiting.

The guide also said the tour is recommended for up to five people and is pet-friendly. Of course my husband, Phil, and our dogther, Agatha, would be joining me. What kind of husband and pawther would I be not to share this with them?

Much like that giddy kid at Christmas or Miss Scarlet awaiting strange gifts, I could not wait too long to dive into this journey. I toyed with going in the Fall, when it was cooler. Ontario had been hit by a heat monsoon, soaking us in our sweat for days on end. But who could wait? We scheduled our trip for July 26. No booking or reserving anything ahead. Just get in your car and go.

The morning of, I consulted the “Before You Go” guide again. I stocked up on some snacks and drinks for the road, including lots of water and treats for Agatha. I even packed a swimsuit and a towel for each of us, hoping there might be a spot to cool down if it got too hot. Once we had coffee in hand, I opened the first location in the parking lot of Starbucks.

How the Locations Work

Quick note about the location booklets. Each booklet has at least two options for stops to visit. They are all within driving distance of each other, with varying levels of activity or differing food and drink options. There is more freedom on the road trip than I thought, which I always appreciate. Given the time frame in the Before You Go booklet, I do not anticipate anyone getting to all the stops if they truly want to experience the locations. Do not treat these locations as a checklist. Take your time and soak in the moments.

My first reaction was shock at the area we would be heading to. I was not anticipating THIS area. I have driven through here but never stop. We opted for the hike over a garden walk. Phil recalled visiting this place when he was a child. We were off to our first stop.

Shrouded by a mature forest with well-maintained trails, we wandered along the marked paths to see some unique historical spots. The trails brought us to two stone structures. Both were used for industrial purposes, but felt old-worldly and organic. After that, we continued on the trail across a small creek with an old stone arch. We ventured into the reserve order of the markers to get to a small series of caverns with ladders to move you from the upper to the lower trail. With Agatha, we had to reverse course and take the flatter trails.

The conservation area was serene. There was a fair number of others on the trail - maybe some of them were out on this route too. One woman noticed the GWT envelope and enthusiastically told us about her adventures. Despite seeing a lot of people at the caverns, we were walking alone most of it. The trees protected us from the sun, but the heat was sticking below the treetops.

Lunch was calling, and we eagerly answered. Ten minutes away, we stopped in a nearby village. I remember driving through decades ago, on my way to visit family in a neighbouring city. The main street was lined with historical homes and lots of shops. It was the type of town you might expect to drive through when heading towards cottage country.

We had two lunch options and opted for the pub-style restaurant with a patio. We got our before a line-up formed, with some people we had seen at the last stop. Agatha was given a cold bowl of water and laid in the shade, while we enjoyed two cold beers from local breweries. The restaurant sits at an intersection, which is quite busy. The line formed next to us, with some hikers at the previous stop waiting for their table. We downed our food and kept on moving.

As I stopped to take a photo of the pub, a Dodge caravan drove in front and screamed, “Ronnnnnn.” It was a fun surprise to run into someone I knew. This friend lives in the area and was on the way to a river with her kids for some tubbing. I did not anticipate seeing anyone we knew on this, so that was a fun treat. The spot she was hoping to get access to the river from was another stop in this packet. However, it was closed for a private event. The “riverside” portion of this trip could easily be attainable in various spots along the main streets. We decided to keep moving. I regret not stopping for ice cream, but a sweet treat will surely come up another time.

Another 13 minutes away would be the cinematic location I was trying to decipher. As a resident of Niagara, we have had our fair share of filming for major movies and television shows. You can walk from my house to a filming location of shows like Hulu’s The Handmaid’s Tale or Netflix’s Self-Made. Don’t forget that A Christmas Story was also filmed in St. Catharines (something I think about whenever I drive by the old Victoria Public School). 

This stop would reignite my rage against Gilead. Hidden at the back of a long driveway is an estate with a farm that was used in the popular dystopian series. Walking around the pristine farm and house, I felt the energy of the set and recalled shots from the show. Even peering into one of the buildings (not the main house, that is a private residence), I could see the actors playing out the show.

Behind the farm was another trail, with weeping willows over the pond and wells. We ventured in a bit, but the heat from the day was taking its toll on us and Agatha. We enjoyed the area before the onslaught of other road trippers came around.

The title grabbed both Phil and me. We both grew up reading these types of books, so it was an immediate recharge of our battery. There were four stops we could make, plus an additional three if we wanted to keep going. While another hike was suggested, we opted for the three more casual stops.

We enjoyed another local beverage at a freestanding brewhouse. The old converted farm housed a full bakery, with coffee and wood-oven pizza made to order. A cute market was taking place. We sat at a picnic table and enjoyed our drinks while Agatha got some shade. The market closed just as clouds began to roll in. Off in the distance, we could see the silhouettes of skyscrapers. We did not have to go far to enjoy some country treasures.

Next, we found a ghost town. An abandoned former factory and housing complex that was standing boarded up. A map displayed what was once the company’s living quarters and worksites. We had to drive by twice to find it, and I wish tours were offered. There is a trail that runs along the site, but we were done with hikes.

Our last stop was for a caffeine boost. Nestled off the main road of another small village, we pulled over just as the shop was closing. They still had plenty of coffee and snacks for us. Phil had a robust carrot cake while I savoured a sticky cinnamon bun. We sat on the porch of the store as the family who runs it closed up. With the last sip of our coffee, the rain rolled in.

Overall, this was the best first Guess Where Trip we could ask for. It was inclusive of the whole family. We did not have to travel too far and were treated to a variety of sights I would not think about.

Round trip, we were gone for 8 hours (not including another stop to catch up with my rapid-riding friend and her family). The information provided gives you all the details you need. A helpful “Travel Updates” section on the website listed possible delays, but nothing stopped us from visiting the available options. 

On that note, I am excited to continue the trip with the alternative stops. When it is cooler weather, the trip will make for a fun Fall activity. I will not need to pack a swimsuit! Plus, the added hotel options are more hidden gems. If a hotel/spa is accommodating to pets, I am there.

For $65, a Guess Where Trip is well worth it. They have a long list of different routes to take. Whether it is a day trip in Ontario, another province, or the United States, I would look at this travel company for help. You may think you know everything, but Guess Where Trips will surprise you.

Check them out online for all the routes and connections to their socials.