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 ...
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Go on your own mini surprise trip with Which Way. Simply pick a card to reveal your next ...
$22
An essential tote bag for your road trip ahead. Carry everything from your surprise package to al...
$5






From $39
This trip is filled with so many hidden gems and charming towns. A countryside brewery or winery, riverside roaming, a seasonal sculpture garden, and unique photo ops galore! This is the perfect trip to do on the way from Ottawa to Montreal.





essentials for your trip

Packed with 500+ of our favourite road trip stops across Ontario, Detour Diaries features 130+...

Track all your local adventures - big or small!
Please see the approximate driving distances below. Please note this just includes round-trip driving distances and not time spent at stops.
Days of the week: Wednesday through Sunday
Months: June through October
Not recommended: Mondays, Tuesdays, November through May, or Holidays
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.
Hidden Hideaways
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.
Please see the approximate driving distances below. Please note this just includes round-trip driving distances and not time spent at stops.
This trip can be done between Wednesday - Sunday and is best done from June - October! If you would like our winery suggestion, this is open Thursday - Sunday.
Please note: some closures may occur on holidays.
A physical trip comes in the mail as 5 sealed envelopes: a "Before You Go" guide, plus 4 surprise stops you open one at a time as your day unfolds. Since it ships, it takes a few days to arrive.
A digital trip has the same 5 sections, sent instantly to your inbox after checkout. Since it's all one document, just go section by section and try not to peek ahead.
Plan for a full day of adventure! Most trips include 4–6 hours of exploring, plus the drive to and from your starting point. We recommend choosing a trip that's about 2.5–3.5 hours round-trip from home for the best experience.
You only need one trip per group. If more than 5 people are going, we recommend putting someone in charge of making reservations (they can peek at the trip by scanning the QR code in the Before You Go booklet).
Just below the trip description, you'll find the town/area where this trip ends. This will give you a good idea of how far you'll be from home at the end of the day.
No advance planning needed for your road trip itself - since it's self-guided, you can pick any date. We do recommend the best days of the week and seasons for each trip, so it's worth checking those before you go. Some stops recommend a reservation, and we'll flag those in your "Before You Go" guide so you know ahead of time.
Of course! After purchasing, you will find hotel recommendations in your confirmation email.
Your trip itself doesn't expire, but details are bound to change the longer you wait to do the trip. We recommend going within 6 months of purchase, and everyone should check our Travel Updates page before heading out.
If you bought the digital version, your link is always kept up to date. If you have a physical trip, scan the QR code in your "Before You Go" guide to check for updates. Most stops also offer 2-4 options, so there's usually something else nearby to enjoy even if one has changed.
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.
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.
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!
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.
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