Coming soon: Baltimore & Washington, DC

Oodles of photo ops and charming small towns. Spooky, abandoned sites and easy, outdoor adventures. Local wineries, breweries, distilleries, cafes and eateries to fuel your road trip energy. And historic hot spots to broaden your knowledge of your own backyard.


How does it work?

Our trips include a 'Before You Go' package and four surprise stops. Each stop is packed with a new destination, specific recommendations, maps, travel tips, fun facts and exclusive 'Guess Where' discounts at select local businesses.

  • Select your trip style.

    Select a day trip based on your interests. Baltimore and Washington DC trips will be available later this summer.

  • Get your package.

    Choose between receiving a beautifully crafted package in the mail OR a PDF (digital version) of the trip which gets sent right to your inbox.

  • Pack your bags.

    Each package includes a 'Before You Go’ booklet that will give you enough information without spoiling the surprise destinations on your road trip.


We're here to help

What is Guess Where Trips?

At Guess Where Trips, we specialize in self-guided one-day surprise road trips. Leave the stress of planning to us! We design each road trips around a general theme, so you will have an idea of what you might get up to during the day, but you won’t know where we’re sending you! We love finding new small businesses, hidden gems, cute cafes, and picturesque towns. 

Need us to take even more stress off of the planning and help you choose a trip? 

Fill out our quiz here to help you decide on a trip!

What will I receive in the mail?

Your road trip includes a well-curated itinerary for the day with a focus on small businesses, cute shops, hidden gems, and unique locations. Our trips come in five envelopes, which are tied with a bow and placed into a folder to keep everything neat and tidy.

Note: If you choose the PDF option, there are no surprise stop envelopes. All of the stops will be sent digitally to your email in one file, so scrolling through the entire document will reveal the surprise stops.

What's not included: Food, drinks, gas, and admission (if there is a fee!) are not included in the price of our trips.

How long will my order take to ship? How much does shipping cost?

For orders over $50, we will ship your package for free via expedited mail. Our expedited option takes 7-10 business days to the United States.

If you need your order earlier, there is an Xpresspost option for $12 CAD, which will take 2-5 business days. Please note: it may take longer to the United States.

Do you have any overnight trips?

Although we cannot book hotels on your behalf, we do recommend extending the adventure by turning your one day road day trip into an overnight getaway (especially if you choose one more than 4 hours round-trip from home!) Keep an eye out for your confirmation email! In it, we will send you a list of our favourite hotels in the end destination if you would like to extend your trip.

How long are your trips?

Each trip takes roughly 6-8 hours to complete - this includes time spent at the recommendation and driving. Under the FAQ section of each trip page, you will find more detailed information about the round-trip driving distance from nearby cities. This will give you a better idea of how much time you can expect to spend in the car, based on your departure location.

Are your trips kid-friendly and pet-friendly?

Kid-friendly: Yes! Almost all of our trips are kid-friendly. We recommend choosing trips shorter in driving distance to ensure it’s a pleasant drive for everyone.

Pet-friendly: Many of our trips are dog-friendly or some what dog-friendly! The trip page itself will let you know if it is okay to bring your pup or not. Note: most restaurants and stores do not allow dogs inside, so most of your day will be spent outdoors if you bring a furry friend along.

Does the cost of the package include the entrance to any activities?

Most of the activities and attractions we recommend are free or have a minimal entrance cost (under $10/per person). We note the approximate costs per person in each trip package. If there is a higher entrance fee, we will recommend a free nearby alternative.