Road Trip Tote Bag
An essential tote bag for your road trip ahead. Carry everything from your surprise package to al...


From $39
This road trip takes you north towards beautiful sights, unusual attractions and secluded waterfalls. The travel time from Toronto is quite far, so be prepared for an early morning or plan ahead by booking one of our recommended accommodations.
Shipping: $8 flat rate, free 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.
FREQUENTLY BOUGHT TOGETHER
Weird & Wonderful Things
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.
Both versions include the exact same trip itinerary - the only difference is how you receive and experience it.
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. Please see our Shipping and Returns section above for shipping times.
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. Trips are received in a PDF format, so you can print this out at home but most trips are 50+ pages.
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.
You can also reference the trip map to view the ending locations here.
All recommendations include full addresses, so you can easily enter them into your GPS and hit the road. You’ll start from home and make your way to your first stop.
Because every trip can look a little different depending on where you’re starting from and which recommendations you choose to visit, turn-by-turn driving directions aren’t included in the itinerary. You’ll just need a GPS app such as Google Maps or Apple Maps to navigate along the way.
We recommend ordering the physical road trips 2-3 weeks in advance to allow enough time for it to arrive by mail.
Digital road trips can be purchased at any time, as the itinerary is sent to you via email once you checkout.
You only need one itinerary per group.
For larger groups:
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).
This person can handle making any necessary reservations and reaching out to the local businesses along the way to confirm they can accommodate your group size, especially for groups of 10 or more. Many of the small local businesses we feature, such as cafés and farm markets, have limited space and appreciate a heads up so they can prepare for a larger group!
Your purchase covers the itinerary itself. Any food, drinks, shopping, gas, parking or attraction fees are additional. We include plenty of free and budget-friendly options throughout our trips, so you can choose how much you'd like to spend.
Plan for a full day! Most trips include about 4–6 hours of stops and driving between them, plus your drive to and from home.
You don't have to do everything - we include multiple options so you can move at your own pace, skip things, or even finish another day. Please refer to the trip map here for all the ending locations.
Absolutely! Just keep in mind that you may not be able to experience 100% of the trip. We include a variety of options at each stop, so there will be plenty to choose from.
Travelling with kids?
If you're bringing kids, we recommend choosing a trip with less than two hours of round-trip driving. Another tip is to have the driver take a quick peek at the itinerary beforehand using the digital link included in your Before You Go guide. This way, you can choose the activities and stops that will be the best fit for your family. And while every road trip includes four stops, there's no pressure to do them all in one day - you can always save a stop for another adventure!
Bringing your dog?
We recommend choosing a trip with plenty of outdoor options and taking a quick look through the itinerary ahead of time to see which stops will work best for you and your dog. Warmer weather is best, when more patios, trails, and outdoor activities are available. There will be dog icons throughout the itinerary to help identify which stops are dog-friendly.
Keep in mind that no matter the season, some stops and activities may not allow dogs, so you may need to skip or adjust certain parts of the trip.
Is the trip wheelchair-accessible?
Some road trips are more accessible than others, and we do our best to include at least one accessible option at each stop. There will be accessible icons throughout the itinerary to identify which spots are accessible for wheelchairs, walkers and strollers.
You can view our most accessible road trips here.
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. Very few stops recommend a reservation, and if they do we'll flag those in your "Before You Go" guide so you know ahead of time.
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.
Of course! After purchasing, you will find hotel recommendations in your confirmation email. You can also see a list of recommended accommodations here.
The suggestions provided are generally in the area of the last stop location.
The trip is meant to be a surprise! But if one person wants to peek ahead to help plan the day, mailed trips include a QR code in the Before You Go guide that links to the digital itinerary. That way, you can plan ahead without opening the envelopes!
We regularly update our trips, but small businesses, hours and attractions can change unexpectedly. Before heading out, we provide you with a link to our 'Trip Updates' list that alerts of any changes to your trip We also include multiple options at most stops, so will always have an alternative nearby.
Pick another day! Or, if you’re feeling adventurous, grab an umbrella and be prepared to get a little wet. The adventure is still waiting for you, rain or shine!
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!
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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.