Kitchener-Waterloo-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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An Adventure is Brewing
$65 CADThis road trip takes you on the perfect summer adventure filled with lavender fields, funky hidden gems, beaches and unique wineries and breweries. This is our featured summer trip and is best taken mid-May to early-October!- Accessible
- Dog-Friendly
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The Small Town Charm Trail
$65 CADYou know those towns that are described as 'blink-and-you'll-miss-it'? They often have the most amazing hidden gems! Get to know a few small pockets of Ontario with this surprise road trip.- Accessible
- Kid-Friendly
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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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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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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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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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Markets to Mountains
$65 CADFrom cute markets to mountainside hikes, Markets to Mountains provides you with all the stops for a cozy yet adventurous day trip in Ontario. We highly recommend booking a hotel at the finishing stop for the ultimate weekend getaway.- Kid-Friendly
- Accessible
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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. -
The Waterfall Route
$65 CADExplore 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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Hops, Hikes & History
$65 CADThere is so much more to this trip than the name implies. From hidden local breweries to unique trails and scenic sights, this trip will take you to a few unknown areas that you’re sure to love!- Kid-Friendly
- Dog-Friendly
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Secrets in the South
$65 CADWith funky markets, scenic roads and the most picturesque towns, you'll love all of the secrets you discover on the road. This trip is best enjoyed between June - September as there are a handful of fabulous seasonal suggestions.- Kid-Friendly
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Historic Haunts
$45 CAD SaleThis haunted history route blends eerie legends and unusual attractions. Visit spots with documented haunted pasts — from towers and ruins to cemeteries — while uncovering the fascinating tales behind them. Please Note: This trip begins in Cambridge and takes place in the same area as Local Markets & Picturesque Towns.- Accessible
- Dog-Friendly
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Spooky Sights & Ghostly Tales
$45 CAD SaleExplore spooky ruins, abandoned buildings, and haunted mansions tied to eerie legends, with a mix of walkable trails, photo ops, and even a chance to dine in a haunted restaurant. Please note: some parts of this trip take place within the city of Hamilton, travellers may encounter some traffic.- Dog-Friendly
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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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From Country to Coast
$65 CADMeander along country roads, explore waterfall wonders, local wineries, breweries, farm shops, and beachside towns. This trip has something for everyone, from families to girlfriend getaways and seniors, you’ll find several hidden gems along the way.- Kid-Friendly
- Dog-Friendly
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Beautifully Haunted
$45 CAD SaleThis outdoorsy, story-filled road trip blends spooky legends with beautiful scenery along a rural driving route. A few local eateries and trails are sprinkled throughout the day to keep your energy up while ghost hunting. Most haunted sites are best enjoyed from the outside, so bring your curiosity and imagination to make the ghost stories come alive.- Dog-Friendly
- 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!- 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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Hidden Gems of Huronia
$65 CADDiscover 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 CADThe 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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All Things Merry & Bright
$45 CAD SaleIf you're looking for a road trip that is full of festivity and holiday cheer, look no further! Meander down decorated streets with a warm beverage in hand, shop for that hard-to-buy-for person at quaint markets, and find your perfect Christmas tree.- Accessible
- Kid-Friendly
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Curiosities & Coastlines
$65 CADWander 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
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Festive Edition: The Sweet & Scenic Route
$45 CAD SaleA little sweet, a little scenic—this road trip blends cozy cafés, local wine, and maple treats with easy winter trails and frozen waterfalls. Perfect for a festive family road trip or romantic getaway!- Kid-Friendly
- Accessible
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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!
