Guess Where Trips

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London, ON
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/

10/10/2026

There’s more than one way to road trip, and we’ve got a few new ones to show you! 🚗

Whether you’re looking for a spontaneous day trip, a weekend away, or a full day of surprises, we’ve got something for every kind of explorer.

Our new Day Trip Boxes, Getaway Boxes and Day Trip Deck give you even more ways to get out and discover somewhere new. And don’t worry, our Classic Road Trips aren’t going anywhere!

Swipe through to see how they all work and find the adventure that’s right for you.

Our new collection officially launches October 15th! Comment “WAITLIST” to get early access and 15% off before the official launch! 👀

So, which one are you most excited to try?

10/06/2026

"What should we do this weekend?" Now you have 20 answers.

Our brand new Road Trip Boxes launch Thursday, October 15th! 🎉

Click the link below to sign up for our waitlist! You'll get first dibs and 15% off your purchase.
https://guesswheretrips.com/pages/collection-waitlists

Can't wait for you to hit the road!

10/05/2026

A surprising number of The Handmaid’s Tale filming locations are tucked right into downtown Cambridge, Ontario, and you can visit several of them in one trip!

We stopped by some of the most recognizable spots from the series, and if you want to see them for yourself, both Riverside Roaming and Historic Haunts will take you there 👀

Save this one for your next Ontario adventure.
https://guesswheretrips.com/collections/all-ontario

10/01/2026

One little box, a whole lot of ways to spend the day 👀

Coffee stops, hidden shops, local markets, sweet treats, good food and a few places you probably wouldn’t have found on your own...

Our physical gift card boxes are part of the sitewide sale, which means they’re 20% off until midnight TONIGHT!

Get them online until October 5th at midnight. After that, they're gone from the website for good and will only be available in-store.

Link: https://guesswheretrips.com/collections/merchandise-gift-cards/products/voucher-box

09/30/2026

Don’t mind us… we’re just gushing over our brand new photos 🤩

Swipe through, fall in love, and shop our 20% off sale until TOMORROW!

Everything’s included except digital gift cards. Happy shopping, friends! 💕

P.S. This song = instant road trip mood. 🎶 What do you blast when you’re driving the backroads?

09/29/2026

Our Fall Sale is LIVE 💥

Sept 29 – Oct 1 only: 20% OFF SITEWIDE! (digital gift cards excluded). No code needed, your discount applies automatically in your cart!

And if you've been eyeing a Physical Gift Card, don't wait! They're only in stock for ONE more week!

09/28/2026

Some places have history... and some places have history that apparently never left 👻

Think old buildings with even older ghost stories, unexplained happenings, eerie local legends and a few stops that might have you questioning whether you’re actually alone.

Trip Link: https://guesswheretrips.com/products/historic-haunts?_pos=1&_psq=historic+haunts&_psid=76e23f717&_ss=e

09/25/2026

The waitlist is officially OPEN 👀💌

Our brand new Road Trip Boxes are coming October 15th! With 20 mini-road trips in every box, your next adventure is always ready when you are 🚗✨

Click the link below to sign up for early access + 15% off before everyone else.

https://guesswheretrips.com/pages/collection-waitlists

09/23/2026

It’s finally here 👀✨

Meet the NEW Guess Where Trips Road Trip Boxes! Each box comes with 20 mini-road trips, so you can pick an adventure whenever the mood strikes🚗💌

Choose from 11 different collections, including Toronto, London, Vancouver, Ontario, New York State & more!

Officially launching October 15th, but our waitlist gets first dibs with early access + 15% off 👀

Waitlist opens Friday… stay tuned! ❤️

Address

London, ON
N5V TO N6P

Website

http://www.guesswheretrips.com/

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