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Tiny Town Tour

J
Hosted By
Jessica
Tiny Town Tour

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.

Meander along scenic roads while stumbling upon charming tiny towns in rural Virginia! This trip has endless photo opportunities, easy outdoor adventures, and plenty of fantastic spots to shop, drink and eat.

STOP 1: With picturesque historic buildings, tasty spots for treats and a little waterfall, this stop has a bit of everything to start your day. Drive time to the second stop is 10 minutes.

STOP 2: An 18th-century town with the most charming main street awaits. We've recommended our favorite spots for a bite, browse or brew. Drive time to the third stop is 7 minutes.

STOP 3: Get your cameras out! It's time for a scenic stroll to a picturesque part of Civil War history. Drive time to the fourth stop is 15 minutes.

STOP 4: A couple of easy outdoor adventures with vast views, or a hidden gem hamlet with a few funky shops. Choose one or two to end the day your way!

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/tiny-town-tour

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Mystery One-Day Road Trips
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Every week on Saturday until October 17, 2025

Needs a location
$65.00