If you’re looking for a fun day trip from Cleveland, you have lots of options, from small towns to big cities to lakeside adventures. But what if you don’t really know where you want to go, and don’t feel like planning it?
Enter a completely new option: a surprise road trip you can complete in a day with Guess Where Trips!
Read on to learn about this really fun way to explore more of Ohio.
What are Guess Where Trips?
Guess Where Trips specializes in carefully crafted “surprise day trips” all across the US and Canada. When you purchase a Guess Where Trips itinerary, you can opt for a physical copy of it, which includes a folder of envelopes to guide you through a one-day road trip. Each itinerary has 4 main stops, and you can choose to go in blind and open each envelope as you go if you truly want to be surprised!
The stops usually include things like outdoor spots, wineries, farms, small local cafes and restaurants, parks/gardens, and small museums. The focus is usually on the sorts of places you maybe haven’t visited before, even if you’re a local.
Guess Where Trips are usually designed for couples or small friend groups, but many of the itineraries can be family- and kid-friendly, too.
Elliot and I tried out a Guess Where Trips road trip ourselves to see what it was all about and had such a good time!
Want to get your own Guess Where Trips packet? Use coupon code CLETRAVEL10 to save 10%!
Guess Where Trips in Ohio
Guess Where Trips currently has 8 different mystery road trip itineraries in Ohio, with 5 of them centering around northeast Ohio.
When you go on the Guess Where Trips website, you can search for trips by destination, along with your preferred season of travel and even your interests or travel needs (such as an accessible trip, or a trip you can do with a dog). They really have thought of a lot with these itineraries!
The Ohio trips to choose from include:
- Waterfall Wanderings (Akron area)*
- Bridges & Beauty (Ashtabula)*
- Woodland Walks & Wineries (Oberlin area)*
- Groves, Gardens & Grapevines (Mansfield area)*
- A Taste of Amish Country (Berlin area)*
- Rivers & Rural Roads (Toledo area)
- Cascades & Colors (Springfield area)
- Storybook Strolls (Hamilton area)
*These trips are the ones easiest to do in a day from Cleveland!
Guess Where Trips review: “A Taste of Amish Country”
The Guess Where Trips mystery road trip we opted to try was the “A Taste of Amish Country” itinerary, since Elliot and I haven’t spent much time in that part of Ohio. I’m not going to give away the exact places we stopped in case you want to try out this trip for yourself, but here’s a bit of what to expect, along with what we loved about this fun day trip option.
Before the trip
We opted for the physical trip guide, which was mailed to our house. (You can also opt for a PDF version of the trip, which costs less – but we really loved the physical version!)
Guess Where Trips does a great job packaging its physical trip guides; ours came gift wrapped, and it was very easy to follow and understand how it was supposed to work.
We opened up our “Before You Go” envelope when we got our packet, which covers lots of essential info for your trip, including tips on days of the week to go or avoid, what to wear, and whether you might need to bring anything specific. (For our trip, the tip to bring some cash was an important one, as many spots in Ohio’s Amish Country are still cash-only!)
I also liked that there was info on driving distances between each stop, how much each part of the trip might cost, accessibility info, and even a land acknowledgment. All without giving away the exact places we’d be going. I was super impressed!
Taking the trip
We opted to take our trip on a Saturday since Sundays were not recommended, and went off the suggestion in our packet to get going early since we’d be driving about 1.5 hours to start our mystery trip.
We opened our first Guess Where Trips envelope in the car after we left home, which gave us all the info for our first stop.
For each stop on a Guess Where Trips itinerary, they actually give you multiple options/suggestions to choose from in close proximity to one another. None of the stops are mandatory (there aren’t any reservations necessary or pre-made, for example), so you can kind of choose based on your interests or the vibe on the day.
We made our first stop at a bakery, and our second stop at an Amish shopping center. The itinerary cards also gave suggestions for extra sightseeing stops along the way, which is how we ended up stopping to see the world’s largest cuckoo clock.
The itinerary gives suggestions that make sense timing-wise – and stops are generally all less than 20 minutes apart. This means you technically could visit multiple places on one “stop” if you wanted, or you could deviate from the itinerary altogether.
For example, we added a stop at a you-pick flower field we randomly drove by, because why not?
Our Amish Country trip also took us to a winery for some drinks and live music, as well as a cool brewery for dinner. Stops that were suggested that we didn’t make included places like a farm, a cheese shop, and an outdoor museum.
But really it’s all up to you!
After the trip
The fun thing about a Guess Where Trips trip is that you could do each road trip more than once and choose different stops each time (though the “mystery” aspect only works the first time).
What we opted to do, though, was pack all the itinerary sheets back into their envelopes and pass our Guess Where Trips box onto some friends for them to use!
Check out this full video review of the trip we did here:
Are Guess Where Trips worth it?
Guess Where Trips cost $65 CAD (about $47 USD) for the physical boxed trip itinerary, or $39 CAD (about $28 USD) for the PDF instant download version. (Yes, the company is Canadian!) You can often find sales – or you can use the coupon code CLETRAVEL10 to save 10% off any time.
Everything is so thoughtfully planned and packaged that I think these are 100% worth it, and would make an excellent gift for a birthday or holiday. You can even add gift wrapping and a cute branded tote bag to the package if you plan to gift it to someone.
I would highly recommend checking out Guess Where Trips, and plan to do more myself in the future! Find their Cleveland area trips here.
READ NEXT: 10 of the Best Day Trips from Cleveland
Would you ever try a surprise day trip like this?
Amanda was born and raised in northeast Ohio, and has always been a fangirl of her home state. Now, she’s sharing her love of the Cleveland area, highlighting all the best things to do, see, and eat in the CLE. She’s been running Cleveland Traveler since January 2019.