STOP 1
Start your day in a cozy cafe and fuel up on sweet treats and caffeine. We've recommended a few different options depending on the direction you're coming from. Drive time to your second stop is 20 minutes.
WHAT TO EXPECT
Explore tiny towns and easy outdoor adventures before cozying up at a local cafe or brewery. During the winter, activities include ice skating and snowshoeing!
Trip Highlights
- Easy hiking trails (snowshoeing and skating available in the winter)
- A local brewery in a historic setting
- Cozy cafes in the cutest towns
- An outdoor sculpture garden for unique photo ops
AVAILABLE TO DEPART
SUGGESTED FOR
- Active families
- Outdoor adventurers
- Foodies
- Couples
Itinerary
STOP 2
Get yourself ready for an outdoor adventure! In colder months, snowshoeing, cross-country skiing, and even tobogganing are available at this conservation park. In warmer months, there are several excellent hiking trails to choose from. Drive time to your third stop is 10 minutes.
STOP 3
A brewery break awaits! After all your outdoor adventuring it's only right that we sit you down for a nice meal. This brewery is housed in a surprising historic location. We've also recommended two alternatives if you're not a fan of brews. Drive time to your fourth stop is 20 minutes.
STOP 4
End the day your way! In winter months, twist and turn your skates over a frozen lake or bundle up for a short trail. In warmer months, we've recommended a few waterside trails with a fantastic photo op. If you're looking for a less active option, explore a couple of local shops & a brewery nearby.
Region
Can depart from
Toronto Area, Kitchener-Waterloo Area, Barrie Area
Before you go
What You'll Need to Bring
Additional Details
- Kid-Friendly
FREQUENTLY ASKED QUESTIONS
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M
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I recommend going on this trip in the fall, we went in the summer and it was too hot for the last stop. Stop two was very quaint and we loved it. The final stop was a lot of walking and would have been more enjoyable in the fall.
Fabulous suggestion, this is definitely a lovely fall trip, especially with the changing leaves! Hopefully you can try it again in autumn, but we're so glad you enjoyed your day out this time too! :)
S
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After reading Moon Road by a Canadian author about a road trip across Canada, our book club had a great time on our Guess Where Road Trip! The stops were well curated from the initial coffee shop to the Brewery lunch spot to the off the beaten path conservation areas we chose to hike. I think I’ve got more friends hooked on Guess Where Trips!
SUCH a cute idea to do a book club day trip! (*stealing that for my book club!*) So happy that you had a great time on the road!
A
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As with all GWT we have done, this trip was so much fun! We liked that it wasn’t too jam-packed so we felt like we could take our time at each stop. The caledon brewery was a highly, along with discovering Klineburg. Only one suggestion for the developers to add : the recommended hikes at the multiple destinations that we did are not shaded. In temperatures of the high 30s, it’s important to tell people to bring hats and water with them. It got extremely hot at times. We can’t wait to do our next one!
Thank you so much for your review! We're so glad you had an awesome time, and we can definitely add hats & water to the packing list. :)
A
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Even though the trip says it's not recommended for dogs, the dining options all had dog friendly outdoor patios and every location allowed on leash dogs on the trails. Winter would be more challenging to bring the pup and get the full experience, but it's perfectly fine in the warmer months.
I do recommend getting to the main first stop as close to 10am as possible. We got to the cafe at 10 and loitered on the lovely patio so were quite hungry for lunch by the time we got to and finished Stop 1, and had to skip ahead to the lunch option at Stop 3. Worth noting though that the recommended (and free) Stop 2 location closes at 4:30 year round (the alternative spot is open later but has an entry fee). Stop 2's trails weren't anything to write home about (it might be better in winter), but it DOES have an 18 hole disc golf course which is a lot of fun (BYO discs). We each clocked about 20k steps that day, though there are alternative Stop 4 options if you're tired (most of these do close at 5pm though). Some proper dinner options would have been nice after such an active day.
Compared to Weird and Wonderful Things and Quintessential Quebec this trip felt like less of an adventure, but it was still a lovely excuse to go to a different area of the city and my mum really enjoyed the day.
A
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We received the trip as a Christmas gift, but waited until May to head out. We had a beautiful spring day, which certainly added to the adventure. We didn't always pick the "Featured Stop", but all the choices sounded great and it was nice to be able to choose. The driving routes were scenic, which was a bonus, the cafe and brewery stops were delicious, the hiking was well marked and rated. All in all it was an amazing day and we would sign up for another trip for sure. Thanks for the adventure!