Guess Where Trips

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Guess Where Trips

We're Guess Where Trips 👋🏻 and we plan one-day self-guided surprise road trips across Canada and the USA! 🇨🇦🇺🇸

No planning needed.
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Just open the envelopes, follow the stops, and enjoy the adventure. 🚗✨

Start here ➡️ https://guesswheretrips.com/

09/04/2026

There’s so much to see when you know where to look 👀

This Ontario road trip is a love letter to small-town charm, with sleepy main streets, winding countryside roads, and just enough quirky roadside surprises to keep you smiling the whole way.

It's the perfect day for anyone who likes their scenery pretty and their pit stops a little weird (in the best way).

Want to know which one it is? Comment "QUIRKY" and we’ll send the trip name straight to your DMs! 🚗

09/03/2026

Okay, but… how does a day trip card game work?! 👀

Take your Which Way? deck with you on the road and let it decide where to go! 🚗

Pick a card → answer the question → turn left or right based on your answer.

Then do it again! Each question shapes your route, taking you somewhere a little different every time. Keep going for as long as you’d like, and when you’re ready to stop, find something fun to do near wherever you end up. 🗺️✨

Get yours! https://guesswheretrips.com/collections/merchandise-gift-cards/products/which-way

08/31/2026

We love summer; we really do… but there’s just something about fall road trip season 🍂🚗

The changing leaves, cozy little stops, crisp air, hidden gems and that first pumpkin-spice-something of the season just hit different.

And the best part? You don’t even have to plan the day.

Pick a trip, open your first envelope and let the fall adventure unfold from there 👀🍁

Who else is starting to get the itch for fall?

08/25/2026

3 DAYS ONLY: BOGO 30% OFF all Surprise Trips!🚗✨

The sale endsThursday, August 27th, so grab your road trip buddy and start planning your next adventure 👀

And just in time for spooky season… Haunted Trips are BACK!! 👻🎃

discover eerie stops, creepy stories and plenty of mystery along the way 🕸️
Find a route: https://guesswheretrips.com/pages/road-trip-map

08/19/2026

Consider this your reminder that you don’t need a plane ticket or a week off work to have a little adventure 💌

Sometimes your next favourite day is hiding just a short drive away.

A Guess Where Trip gives you an excuse to get out of your usual routine, explore somewhere new and spend the day uncovering hidden gems one stop at a time.

From cute local finds and gardens to drinks, views and places you probably never would’ve discovered on your own✨

Stop waiting for the “perfect time” and make a day of it🤍

08/17/2026

How well do you know Ontario’s hidden gems? 👀📍

We’re putting your road trip knowledge to the test!
Take a close look at the clues in this video and see if you can figure out which Ontario town we’re exploring 🚗✨

Think you’ve got it? Drop your guess in the comments before we reveal the answer on our stories tomorrow 👇

No cheating 😉

08/14/2026

The perfect Ontario summer combo: ice cream + a stroll🍦☀️
We paired some of our favourite ice cream stops with a nearby spot to wander, explore and make a day out of it:

🍦 Terra Cotta Country Store + Cheltenham Badlands
🍦 Sky Ranch Drive In + Menesetung Bridge
🍦 Slickers County Ice Cream + Sandbanks Provincial Park
🍦 Shaw’s Ice Cream + St. Thomas Elevated (Sculpture) Park

Save this for your next summer road trip 🚗💛

Which pairing are you trying first? 👇🏻

08/13/2026

Big news: our digital gift cards just got a major glow-up! ✨

For years, you could only grab a gift card at one price: $74, locked in for one surprise road trip. And for years, you asked us the same question: “why can’t I just choose the amount?”

We heard you. Now you can pick your own denomination! Enough for a surprise road trip, a Detour Diaries guide, or any of the fun add-ons in between. 🛣️

And because every gift should match the moment, we designed a handful of adorable new card icons to choose from.

Go on, share this with someone who should get you something GWT as a gift. 👀🎁

08/12/2026

Sometimes the best part of a road trip is simply slowing down🌿

A quiet stroll, a hidden waterfall, a peaceful view, and nowhere else you need to be.

Consider this your reminder to take the scenic route every once in a while🤍

Where do you go when you need a moment of peace?

08/10/2026

Your next road trip could look a little familiar… 🎬👀

From The Fault in Our Stars and The Blues Brothers to Sweet Home Alabama and Hocus Pocus, some of the most iconic filming locations are hiding in places you can actually visit.

Which one would you recognize right away? 🍿

Virginia B. Fairbanks Art & Nature Park
💌 Elegant Estates & Outdoor Art

Joliet Prison
💌 Eerie Escapes

Oak Hill & Martha Berry Museum
💌 A Drive Back in Time

4 Ocean Ave, Salem
💌 Witchy Wonders

Address

London, ON
N5V TO N6P

Website

http://www.guesswheretrips.com/

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