Home Lifestyle This Road Trip Planning Company Recently Launched in New Jersey

This Road Trip Planning Company Recently Launched in New Jersey

by The Montclair Girl Team
0 FacebookTwitterPinterestEmail

We love traveling, but sometimes, it can be difficult to plan a trip to a place you haven’t quite explored yet. Or if you’re like us, you simply might not have enough time to research and put together an itinerary worthy of a getaway. But have no fear — that’s where Guess Where Trips comes in. This road trip planning company recently launched in New Jersey and plans your trips for you, fit with surprise stops and local travel tips all around the North Atlantic/New England area. Keep reading to learn more about Guess Where Trips’ recent launch in New Jersey + how it works.

guess where trips

All About Guess Where Trips

Guess Where Trips creates personalized one-day surprise road trips across the U.S. and Canada, with its most recent launch in New Jersey for customers who are looking to explore a certain area. You can choose a starting point and destination, and let the Guess Where Trips team do the rest of the planning for you (pretty awesome, if you ask us). 

The Ivy at Chatham

guess where trips

“We give [customers] the chance to experience something new, discover a new favorite local business, and learn something about their own backyard,” said Jessica Off, founder of Guess Where Trips. “The trips are flexible, the stops are self-guided, and the same trip can be done multiple times as we recommend so many different options.”

Guess Where Trips also created a quiz for interested customers to narrow down their options and choose the right destination that suits their interests.

guess where trips


How It Works

To let Guess Where Trips plan your next adventure, first select your trip, including your departure, desired destination, and travel preferences. For example, if you’re into haunted or historical attractions, you can choose some spooky locations along your trip.

“You’ll then get mailed (we provide free shipping), a beautifully wrapped package with five envelopes,” Jessica told The Montclair Girl. “The first envelope AKA the Before You Go Guide provides you with an overview of your day with clues on where you’re going. It includes a packing list, playlist recommendations, when to leave, etc. The day of your trip, you open up the first envelope to discover where you’re headed.”

guess where trips

Each envelope also contains a booklet that outlines your recommended route, places to eat, and featured stops. Guess Where Trips carefully curates your itinerary based on your preferences, so you’ll be sure to experience everything you set out to do.

The company even provides travel updates that report any closures or cancellations of eateries or events listed on your trip. MG Pro Tip: Definitely make sure to check the page the morning of your trip so there are no road or route surprises.

guess where trips


Female-Founded, Pandemic-Era Business

Jessica started Guess Where Trips in January of 2020 — right before the COVID-19 pandemic.

“This stemmed from a Christmas present I gave my parents years ago,” said Jessica. “I loved planning it, and they obviously loved the experience so I decided to make a business out of it. Three and a half years later, we offer trips across Canada and in 14 states!”

guess where trips

^ Jessica Off, Founder of Guess Where Trips

While the pandemic initially impacted the business and halted its sales, the business soon took off again once May hit. During that time, Jessica and her team were able to plan safe, socially distanced trips for customers to escape the isolation of previous stay-at-home orders.

Recently, the Guess Where Trips team visited Montclair and adored our town’s energy.

“It was so fun researching and exploring this area!” Jessica said. “There were so many charming streets, historical fun facts, and funky gardens. It was really hard creating a trip to Montclair with all the amazing and different stops to pick from!”

guess where trips

get started button

Guess Where Trips has officially launched in New Jersey and is booking trips around the North Atlantic/New England area; with trips available in 14 US states + across Canada.

You can contact Guess Where Trips by emailing questions@guesswheretrips.com.

also appears in

0 comment