Man with rain jacket walking along a leaves-covered forest trail.
Hiker walking on top of rocks over a river.
Woman with backpack walking along a green forest trail.
Woman picking up a beer from a flight of beer samples.
Table at a cafe with a cappuccino and a croissant.
Woman standing on a snowy bridge in the middle of a forest

Escape to Nature

4.7 (28 reviews)

From $39

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!

When to Go Weds - Sun
ends near Orangeville, ON

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  • Free Shipping on Orders $100+
  • 30-Day Returns & Exchanges
  • No Booking Required

essentials for your trip

Detour Diaries: Ontario

Detour Diaries: Ontario

Packed with 500+ of our favourite road trip stops across Ontario, Detour Diaries features 130+...

$59
Lilac Road Trip Journal

Lilac Road Trip Journal

Track all your local adventures - big or small!

$25

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
  • Multiple recommendations included on every stop

How Long Is This Trip?

Please see the approximate driving distances below. Please note this just includes round-trip driving distances and not time spent at stops.

From Toronto:
2 hours and 40 minutes / 177 km

From Oshawa:
3 hours and 17 minutes / 260 km

From Burlington: 
2 hours and 48 minutes / 221 km

From Kitchener:
3 hours and 15 minutes / 228 km

From London:
4 hours and 57 minutes / 417 km

From Niagara Falls:
4 hours and 5 minutes / 358 km

From Barrie:
2 hours and 47 minutes / 205 km

From Collingwood:
3 hours 35 minutes / 236 km

When Can I Go?

Days of the week: Wednesday through Sunday

Seasons: Year-round

Not recommended: Mondays, Tuesdays, Holidays

Shipping & Returns

Shipping: Free shipping on orders over $100. Standard shipping takes 4–10 business days. Need it faster? Choose the fastest option at checkout for 2–4 business day delivery.

Returns: Not the right fit? Reach out within 30 days of purchase to start a return. Products just need to be unopened, unused, and in their original packaging, return shipping is your responsibility. Digital trips, gift cards, and opened products can't be returned.

Exchanges: Want a different trip instead? Email us at questions@guesswheretrips.com within 30 days of your order, there's a small $8 reshipping fee to send your new pick out. Digital trips cannot be exchanged.

Read our full return policy →

Escape to Nature

4.7 Physical Package

Here's How It Works

Browse by location and find a surprise trip that fits your day. Every route is road-tested by our team.

Your surprise destinations stay sealed until you're ready for them. One envelope at a time on the road, all day long.

Hidden gems, local favorites, and stories you won't find on Google. That's what's waiting for you.

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Frequently Asked Questions

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What People Love About Our Trips

Rated 4.9/5.0 stars

What an Amazing Day!

Our daughter gave us this for Christmas and we finally pulled it out this week, July now. We love a road trip and loved the mystery of each new step. Great things to see and experience. Great restaurants to enjoy. I’ve recommended it to all my friends. Amazing.

Donna S. 🇨🇦

First Time…There WILL be a second!

Knowing the area we went I was very pleasantly surprised. We saw things I did NOT know existed! One of the stops was closed however we were able to walk up to it for a photo.

Mary Y. 🇨🇦

Great day away!

Did this trip with my mom for Mother’s Day. Lots of quaint little stops and places to explore! They also gave a few options at each stop so you could choose your own adventure! Will definitely be doing this again, had a wonderful time!

Megan M. 🇨🇦

Road Tested by Our Team

Our team spends 40+ hours researching, driving, and vetting every route: talking to locals, discovering hidden gems, and making sure every stop is worth your day.

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"The most fun, stress-free way to explore Ontario”

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“Trust me, you need to try this”

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“I still can’t get over how fun it was”

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We Remember Experiences, Not Things.

Research consistently shows that spending time together creates more lasting happiness than buying more stuff. Every Guess Where Trip is thoughtfully planned to help you reconnect, explore, and create memories that last long after the day is over.