Guess Where Trips launches surprise road trips in DMV region

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Pack your bags, D.C.!

Guess Where Trips is taking the hard parts out of travel, so everyone can discover a new favorite place or hidden gem. The popular surprise road trip company today unveiled five new itineraries, all accessible from the D.C. Metro area, with stops from Baltimore to Gettysburg.

Founded in 2020, Guess Where Trips offers all adventurers the chance to be surprised by their travel while ensuring they get to experience the best off-the-beaten-path treasures and tried-and-true favorites a destination has to offer. Unlike tours, guidebooks and blogs, which often suggest popular attractions anyone can find with a quick Google search, the creators of Guess Where Trips have spent hours thoroughly vetting and curating each itinerary…so you don’t have to.

Here’s how it works:

• Customers select a trip online based on their interests. From natural wonders and paranormal hotspots to discreet filming locations, hidden selfie spots and low-key foodie favorites, there’s a trip for everyone. Guess Where even makes it easy with a quiz to find the best trip for every traveler.
• Once customers have picked a trip, they wait for the package with their itinerary and the “Before You Go” envelope to arrive in seven to 10 days. Travelers who are looking to get up and go with no wait time can also choose to have the itineraries delivered directly to their email.
• Then they pack their bags and hit the road! Destinations for each road trip are revealed throughout the day as travelers open the series of envelopes that contain directions to each surprise stop on the self-guided tour.

Because the spots have all been explored by travel experts, Guess Where Trips will show everyone something new. And because no one will have to spend hours planning, everyone can sit back and enjoy the ride. They’re perfect for locals looking to explore their hometown in a new way, couples seeking a romantic getaway, friends ready for a fun girls’ trip, or families looking to spend time together.

There are trips for every season and many that can be completed year-round, so a Guess Where itinerary makes the perfect gift for any occasion.

Each trip takes six to eight hours. Only one itinerary is required per group.

Each of the DMV area trips costs $65 and promises a collection of weird and wonderful stops.

The new offerings include:

• Tiny Town Tour: Meander along scenic roads and stumble upon charming tiny towns. This trip has endless photo opportunities, easy outdoor adventures and plenty of fantastic spots to shop, cheers and eat.
• Waterside Bliss: Start the day with a coffee on the water before exploring historic gems and a waterside boardwalk. End the day with a choice between a funky winery or a walk along the beach.
• Hikes, Haunts & History: Discover a hidden schoolhouse, learn about an iconic battle, and explore a famous graveyard before ending the day with a hike or a trip to a mountainside winery.
• Secrets of Gettysburg: Explore Gettysburg… with a twist! The Guess Where Trips team organized this trip in a scavenger-style format, making it easy (and fun) to learn about the history of Gettysburg while also discovering hidden gems along the way.
• Winding Roads & Historic Gems: The first few stops will lead to funky farms with furry friends, optional wineries and so many hidden gems. The day will end in an iconic road trip town with so much to see and do.

The team at Guess Where Trips is always looking for more secret spots and creating new itineraries, so adventurers can expect to see more trips throughout the United States soon.

In addition to the DMV area itineraries, Guess Where offers 50+ trips available across Canada, Florida, Georgia and North Carolina.

To view or download visuals, click here.

To learn more about Guess Where Trips, visit

About Guess Where Trips
Originally launched in Canada in 2020, Guess Where Trips offers over 50 trips in four Canadian provinces and has expanded to offer trips in several locations in the United States including Washington D.C., Florida, Georgia and North Carolina. With tens of thousands of happy customers, the company continues to expand throughout the U.S. and support small businesses across North America.