Kellogg GWT
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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Free Add On: Road Trip Gift Wrapping
SaleRegular price $14.00 Sale price $0.00 CADUnit price perA reusable gift box with magnetic closure - perfect for presenting their surprise trip and storing souvenirs after the adventure.Sale -
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 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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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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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
$39 CADThis 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
$39 CADExplore 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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From Country to Coast
$65 CADMeander along country roads, explore waterfall wonders, & visit local 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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Bridges to Beaches
$65 CADPicturesque bridges to sandy beaches and everything in between. This trip takes you off the beaten path to some of our favourite places in Ontario.- Accessible
- Kid-Friendly
- Dog-Friendly
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Southern Express
$65 CADThink cozy bakeries, swim spots, easy hikes, and wine with a view, all wrapped up in one charming escape. You’ll wonder how this area stayed off your radar for so long!- Kid-Friendly
- Dog-Friendly
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Road Trip Tote Bag
SaleRegular price $20.00 Sale price $5.00 CADUnit price perAn essential locally made tote bag for your road trip ahead. Carry everything from your surprise package to all the snacks and goodies you'll pick up throughout your day.Sale -
Road Trip Game Pack
Regular price $12.00 CADUnit price perKeep the young ones busy with a fun game pack to play with on the road! Dozens of games and activities to keep kids of all ages entertained. -
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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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
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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!
