Birdseye view of a winding river alongside forests.
Woman sitting on a rocky shore overlooking a river.
Wooden bridge leading into a green forest.
Two people clinking their glasses at a brewery.
Woman holding onto a takeaway coffee cup and a baked good.
Close up of an old red brick building underneath a vibrant blue sky.

Riverside Roaming

4.4 (62 reviews)

From $39

Start 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!

When to Go Weds - Sun
ends near Ayr, ON

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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

  • Grab a coffee in the most adorable bookstore cafe
  • Go shopping in a historic mill
  • Head to a brewery for lunch
  • Choose between a few boardwalk trails
  • Countryside farm shops
  • Multiple recommendations included on every stop

How Long Is This Trip?

See the approximate total round-trip driving distances/times below. These are driving distances only and do not factor in time spent at stops.

  • From Toronto: 3 hours and 12 minutes / 251 km
  • From Brampton: 2 hours and 55 minutes / 256 km
  • From Oshawa: 4 hours and 7 minutes / 354 km
  • From Oakville: 2 hours and 41 minutes / 222 km
  • From Hamilton: 2 hours and 5 minutes / 145 km
  • From Kitchener: 1 hour and 38 minutes / 86.5 km
  • From London: 2 hours and 50 minutes / 222 km
  • From Niagara Falls: 3 hours and 27 minutes / 292 km
  • From Barrie: 4 hours and 18 minutes / 385 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 →

Riverside Roaming

4.4 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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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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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.