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Charming Curiosities

J
Hosted By
Jessica
Charming Curiosities

Details

This is a one-day, self-guided surprise road trip. Upon signing up you'll receive a beautiful package in the mail with a Before You Go guide, and four mystery stops (shipping is included). This self-guided surprise itinerary is best done Wednesday-Sunday.

With a few haunted stories, trails with a unique past, and charming historic mansions, we're confident you'll find new favorite spots to explore when you hit the road with this surprise trip.

STOP 1: Start the day at an art centre with an interesting past or stroll the picturesque streets of a charming small town. Drive time to the second stop is 10 minutes.

STOP 2: It's time to pick your park! Whether you want a historic site or to stretch your legs on a boardwalk trail, we've got you covered. Drive time to the third stop is 15 minutes.

STOP 3: Choose between a haunted church, another easy boardwalk trail, or an incredibly scenic local winery. Drive time to the fourth stop is 20 minutes.

STOP 4: History, brews, and bites - oh my! Your camera roll will be full after this end destination, and you'll likely want to return for years to come.

Important Details:
Most of the recommendations are free to enjoy. Please note that food and drinks are not included.

  • This is a self-guided road trip—you’ll need access to a car.
  • We recommend a group of up to 5 people per vehicle.
  • Your itinerary includes a Before You Go Guide and 4 surprise envelopes, each with a mini booklet of curated stops.
  • The trip can be started from anywhere in or around the DC area.

Have questions? Email us at **questions@guesswheretrips.com** or send us a message on Instagram: @guesswheretrips

Our one-day surprise road trips have been highly reviewed in The Washington Post. The review can be found here: https://www.washingtonpost.com/travel/tips/mystery-road-trip-guess-where/

More information on the itinerary details and to purchase (use promocode MEETUP15 for 15% off): https://guesswheretrips.com/products/charming-curiosities

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Mystery One-Day Road Trips
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Every week on Wednesday, Thursday, Friday, Saturday until October 31, 2025

Needs a location
$65.00