Collingwood-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 and Picturesque Towns
$65 USDOne 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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Vistas & Caves
$65 USDThis 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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Road Trip Gift Card
Regular price $74.00 USDUnit 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. -
The Waterfall Route
$65 USDExplore a variety of waterfalls, charming towns, funky restaurants and several photo ops throughout the day! This trip is perfect for spring - fall travellers. Waterfalls may dry up in extreme heat.- Kid-Friendly
- Dog-Friendly
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Escape to Nature
$65 USDExplore 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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Hidden Gems of Huronia
$65 USDDiscover the endless charm of a lesser-known area that is full of haunted history, picturesque trails, cute small towns and farm-fresh flavours. We're sure you'll want to keep coming back for years to come!- Kid-Friendly
- Accessible
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Bayside Wonders
$65 USDThe perfect blend of charming small towns, farmers markets, and wine tastings mixed with epic waterfalls and a couple unique trails. Bayside Wonders is a bit further, which makes for an incredible weekend getaway! Please note: A few recommendations have been moved from The Waterfall Route to this new trip. There are still tons of new spots to explore!- Kid-Friendly
- Dog-Friendly
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Curiosities & Coastlines
$65 USDWander through eerie ruins, stop at offbeat roadside finds, explore historic small towns, and relax by the shores of Lake Huron. This laid-back Bruce County adventure perfectly mixes local legends, great eats, and scenic spots!- Kid-Friendly
- Dog-Friendly
- Accessible
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!
