STOP 1
Grab a tempting treat to-go before visiting a truly unique piece of Canadian history. The drive time to the second stop is 10 minutes.
WHAT TO EXPECT
A 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!
Trip Highlights
- Tasty maple bites
- Snap a photo of a funky bit of Canadiana
- A few easy outdoor adventures
- Farmers markets with sweet treats
- Sip local wine & take in the views
AVAILABLE TO DEPART
This trip can be taken year-round between Wednesday to Saturday. If you're traveling between May and December, you can also take this trip on a Sunday!
SUGGESTED FOR
- A girlfriend getaway
- Romantic date days
- Photographers
- Easy outdoor adventurers
Itinerary
STOP 2
Savour small town charm, sip local wines, or stroll along an easy trail. The choice is yours! The drive time to the third stop is 12 minutes.
STOP 3
A quick outdoor adventure is sure to please in any season of the year. Then, head to a yummy farm market that specializes in all things maple! The drive time to the fourth stop is 10 minutes.
STOP 4
Whether you’re up for a waterfall adventure, or you want to enjoy another glass of wine, we’ve got you covered.
Region
Can depart from
Toronto Area, Kitchener-Waterloo Area
Before you go
What You'll Need to Bring
Additional Details
- Accessible
- Dog-Friendly
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Customer Reviews
Based on 6 reviews
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J
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I loved every little detail in this trip. It was so engaging and perfectly close enough to each other
A
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Me and my boyfriend went for our two year anniversary! It was an amazing time and we enjoyed it. Definitely worth the visit to all of these places and we want to redo this trip again in the summer as well to see all of the places in a different setting! Amazing time and so excited to do another trip with this company!!
B
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This was an absolute blast! My friends had surprised me with this road trip for my birthday in February 2025. We were absolutely in love with how cute the package comes and so glad we had the physical envelopes to go through before heading out to our next destination. There was so much to do and see it was incredible to not have to do any of the research and to be able to just sit back and drive. The destinations take you so many hidden gems that are guaranteed to enhance the experience and keep you busy throughout the day. Throughout the day you can appreciate the time and care that was put into planning and organizing the trip and make it the great time that it was! Locals and strangers stopped us to comment on the envelopes to ask our experience or share their own which made it fun to connect with the local area! The trip ended at a location which was housing a stray cat that they had fixed up and were looking for a permanent home. One of my friends ended up taking the cat home and is now happily in his furever home! An amazing and unforgettable experience! I already purchased 'Markets to Mountains' trip to do with my siblings. Highly recommend for gifts, siblings, couples, families, friends, EVERYONE!
R
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This trip was so much fun! Guess where trips are the best for a day date that's out of the ordinary
Y
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It truly was such a well curated trip! My partner and I kept telling each other that we wouldn’t have discovered these parts of Ontario if it weren’t for this experience. My favourite part of the trip was not only the well thought out package and quaint stops, but how welcoming and happy everyone was at each stop we went to knowing we came into their establishments/area because of GuessWhereTrip! I cannot wait to experience more trips in the future!
We're so happy that your trip exceeded your expectations! We love finding small businesses that are both great finds AND super friendly/welcoming to our travellers!