Which Way? A Surprise Road Trip Card Game
Go on your own mini surprise trip with Which Way. Simply pick a card to reveal your next ...
200,000+ road trips soldDiscover Places You'd Never Find
A surprise road trip, planned down to the last stop - by us. Just pick a trip, get in the car, and find out what's waiting for you.
Surprise one-day road trips
Self-guided & fully flexible
Hidden gems & Local stops
Road-tested by real people
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.
2,328 verified reviews
See Where Our Road Trips Took Them
“It's such a fun way to explore!”
@emilywhoexplores
“Found some new favorites”
@pitstopswithtori
"Every stop felt like a hidden gem"
@lexy_explores
“Perfect for a weekend adventure”
@paubarragann
"Skip the planning and just GO!"
@thewatsonpost
What's Inside Your Surprise Packages
Mailed Road Trips
A beautiful package, ready to gift or save for the perfect day.
$65- Four sealed surprise stop booklets
- A handy Before You Go guide
- Printed, packed & shipped directly to you
- Arrives in 2–8 business days
PDF
Digital Road Trips
Same trip, in your inbox instantly. Perfect for spontaneous adventures.
$39- Instant download, no waiting
- Designed to be viewed on your phone
- Ideal for last-minute weekends & travel
- Upgrade to the mailed version anytime
Free shipping over $100
Covers your whole group
No booking required
2,328 verified reviews
Thousands of Five-Star Reviews
Perfect birthday gift!
“I bought this for my husbands birthday. From the coffee shop, to the towns locals giving us some fun history ...it was amazing!”
Such a nice surprise!
We did the hops, hikes and history tour and it was so much fun! My husband begrudgingly came along for something I wanted to do, but he thoroughly enjoyed himself, as did our dog!?
What an incredible experience!
Yesterday, we completed the Hidden Hideaways trip, and it exceeded every expectation. It was one of the most enjoyable day trips we’ve ever taken!
Fun date day without having to plan!
Fun date day without having to plan! Took all the suggestions and made the most of our day. Didn't get to our final stop because we took so long enjoying the first three. Can't wait to do another one.
our story
Meet the Team
It started with a woman who wanted better weekends
Guess Where Trips started in January 2020, when founder Jessica Off created a scavenger-style surprise road trip as a gift for her parents. Six years later, we're a small Canadian team that has spent over 4,800 hours on the road so you don't have to figure it out yourself.
Woman-Founded
Small Canadian Team
Independently Owned
Every Stop Supports Local
Every business on our routes is local and independent. We've seen what showing up means. When you go, you're giving a small business a really good day too.
Local breweries
Charming small towns
Cozy cafés
Scenic lookouts
Farmers markets
Quirky photo ops
Roadside oddities
Hidden beaches
Independent bookshops
Heritage trails
