Woman looking out of car window.
People clinking wine glasses.
Photo of snowy hill taken from car.
Mother and daughter walking down path.
Photo of a photo of food being taken from a phone.
Family walking through grass to an old barn.

All the Pretty Things

4.5 (37 reviews)

From $39

Within easy driving distance of Ottawa or Kingston, this thoughtfully planned road trip is filled with charming stops, historic attractions, and standout restaurants and wineries. It’s an easy and enjoyable way to explore the region and take in beautiful scenery along the way.


When to Go Weds - Sun, mid-May to October
ends near Westport, 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

  • Several viewpoints
  • Quaint towns and hamlets
  • A variety of hiking options
  • Delicious restaurants
  • A very cool winery
  • 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 Ottawa: 3 hours and 26 minutes / 276 km
  • From Kingston: 2 hours and 46 minutes / 195 km
  • From Belleville: 4 hours and 5 minutes / 333 km

When Can I Go?

Days of the week: Wednesday through Sunday

Seasons: Spring through Fall

Not recommended: Mondays, Tuesdays, Holidays or Winter

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 →

All the Pretty Things

4.5 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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“It was such a fun experience!”

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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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“Guess Where Trips thinks of everything”

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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.