For those who love a good surprise but dread the details of travel planning, an Ontario company is offering the perfect solution: mystery road trips to hidden local gems.
Founded by Jessica Off, Guess Where Trips creates self-guided one-day itineraries that lead travelers through unexpected stops across Ontario and beyond. Each package comes with a “before you go” guide and four surprise destinations that could include farmers markets, lavender fields, wineries, breweries, covered bridges, or small-town treasures. Customers receive maps, recommendations, travel tips, and fun facts—without ever knowing what’s next until they arrive.
Launched in 2020 with just two itineraries, the business has grown rapidly, now boasting over 150 trips across four Canadian provinces and 20 U.S. states. While cross-border demand has been limited by tariffs and trade challenges, Ontario sales have surged, especially among Toronto-area travelers seeking unique local experiences.
Day trips cost $65 and can be purchased as mailed packages or instant digital downloads. Seasonal themes, such as Halloween haunted tours or festive holiday adventures, add to the appeal. Some trips highlight breweries and wineries, while others focus on nature, markets, or small-town charm. Most are designed as single-day outings, though travelers can extend their adventures with hotel stays.
Off said the idea came after planning a surprise road trip for her parents in Prince Edward County. The experience was so well-received that she turned it into a business. Today, her 11-person team researches, tests, and curates every itinerary, with a focus on supporting local businesses rather than chain establishments.
The trips have also become a popular gifting option, offering a memorable experience instead of a traditional present. Building on that success, Guess Where Trips is preparing to open a flagship store at the redeveloped Kellogg’s factory in London, Ontario, and will soon release Detour Diaries, a book highlighting quirky roadside stops across the province.
For those eager to explore their own backyard in a new way, Guess Where Trips promises a blend of spontaneity, discovery, and adventure—without the hassle of planning.