Guess Where Trips launches surprise road trips in Connecticut

Four Connecticut itineraries available now; 13 trips launching across the Northeast

HARTFORD, Connecticut, 2023-Sep-19 — /EPR Network/ — Pack your bags, Connecticut!

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 four new itineraries, all accessible from Connecticut, with stops from Hartford to New Haven.


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 trips costs $65 and promises a collection of weird and wonderful stops.


The new offerings include:

  • Vibrant Vistas & Picturesque Towns: Hit the road and explore easy outdoor adventures, outstanding views and small towns that inspired Stars Hollow in Gilmore Girls. (2 hours and 40 minutes round-trip drive time from New Haven / 98 miles)
  • Coastal Connection: Feel the ocean breeze in your hair as you go from beaches and boardwalks to independent shops and eateries. There are a few unusual surprises in this trip that will keep you on your toes!  (2 hours and 15 minutes round-trip drive time from New Haven / 117 miles)
  • Hudson River Hideaways: An iconic road trip route with a twist! Discover countless hidden hideaways along the Hudson including; crumbling ruins, quaint towns, spooky cemeteries and more.  (3 hours and 55 minutes round-trip drive time from New Haven / 117 miles)
  • Funky Farms & Storybook Tales: It’s no wonder authors flocked to this area of Massachusetts for inspiration! Head out on a picturesque drive and discover farms, boardwalk trails, lots of quirky history and so much more.  (2 hours and 5 minutes round-trip drive time from New Haven / 73 miles)


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 North Atlantic/New England area itineraries, Guess Where offers 50+ trips available across Canada, the Washington D.C. metro area, Florida, Georgia and North Carolina.


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.


Matched content

Editor’s pick

Express Press Release Distribution