Hamilton-Area Road Trips
Select a trip that works with your driving and travel preferences. If it's hard to choose, take our road trip quiz instead.
Browse all trips
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Local Markets & Picturesque Towns
$65 CADOne of our best-selling trips, and for a good reason. Stops include historic towns, local markets, eateries and hidden gems. This trip makes a great gift because of its versatility.- Accessible
- Kid-Friendly
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An Adventure is Brewing
$65 CADA summer road trip within driving distance of Toronto, Hamilton, Kitchener, and London with beaches, wineries, and hidden gems.- Accessible
- Dog-Friendly
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Road Trip Gift Card
Regular price $74.00 CADUnit price perGive the gift of a one-day surprise road trip with Guess Where Trips®! Valued at $74, this voucher covers the full cost of any of our mailed road trips, including tax and standard shipping. The recipient can choose any surprise road trip that suits them, and it will be shipped right to their door. These gift cards never expire. -
Vistas & Caves
$65 CADThis road trip is a quick jaunt north of Toronto and is perfect for the outdoor enthusiast. It really is the perfect mix of everything.- Accessible
- Kid-Friendly
- Dog-Friendly
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Country Farms & Furry Friends
$65 CADAlpacas, donkeys and goats - oh my! Start your day off at a funky country market, before hanging with the birds and ending the day with some furry friends.- Kid-Friendly
- Accessible
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Funky Florals and Fine Wines
$65 CADThis pretty little road trip offers quite a few hidden gems combined with a few iconic attractions. Must enjoy: wine, food and flowers.- Accessible
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Riverside Roaming
$65 CADStart your day in a picture-perfect town by the river before strolling along boardwalks, dining at a funky distillery, indulging at farm shops and so much more. This trip is a nice distance from the city and can be done year-round!- Kid-Friendly
- Accessible
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Escape to Nature
$65 CADExplore tiny towns and easy outdoor adventures before cozying up at a local cafe or brewery. Optional wintery activities include ice skating and snowshoeing! Please note: this trip is similar to the Sport Chek Winter Trek for Toronto.- Kid-Friendly
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The Sweet & Scenic Route
$65 CADA little sweet, a little scenic - this road trip blends cozy cafés, local wines, and maple treats with easy trails, waterfalls, and serene ponds. Perfect for a girls' getaway or a romantic day trip! *Note that this trip can be taken in the summer months; however, the waterfalls may slow to a trickle in the hot weather!- Accessible
- Dog-Friendly
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The Whimsical Route
$65 CADGet 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!- Kid-Friendly
- Accessible
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Detour Diaries: Ontario
Regular price $59.00 CADUnit price perPacked with 500+ of our favourite road trip stops across Ontario, Detour Diaries features 130+ detailed, user-friendly maps and over 300 pages organized by major highways to make planning effortless. You’ll also get bonus QR code access to an interactive mobile map for easy navigation on the go.
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The Cheese & Charm Trail
$65 CADCalling all cheese lovers and countryside explorers! This deliciously charming road trip winds through scenic backroads filled with flower farms, local markets, dairy stops, and small-town surprises - perfect for a day of snacking, wandering, and saying “just one more stop".- Accessible
- Kid-Friendly
CAN'T DECIDE?
Take Our Quiz to Find Out
Select your region and interests to find the best trip for you.
Gift-a-Trip
The ultimate present for the avid traveller. Select a digital or mailed 'Gift-A-Trip' option that covers the full cost of one of our road trips. We promise you this will be one of the most memorable and unique gifts they'll ever receive!
