What we’re about
Welcome to Mystery One-Day Road Trips Meetup! Are you craving some adventure and excitement in your weekends? Join us for our fun-filled group outings that will take you on thrilling and mysterious road trips to various destinations. Whether you love exploring nature, finding quirky roadside stops, or simply enjoying a day out with like-minded individuals,this group is perfect for you. Get ready for memorable day trips with lots of surprises along the way. Let's hit the road together and make the most of our weekends! Join us now and let the mystery unfold.
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
Upcoming events (4+)
See all- Charming CuriositiesNeeds location$65.00
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
- Charming CuriositiesNeeds location$65.00
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
- Haunts, Hikes & HistoryNeeds location
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.
From haunted happenings to easy strolls and historic hot spots, this trip has a little bit of everything for everyone!
STOP 1: Start your day with a quick walk over babbling creeks and bridges to a surprise photo op. Drive time to the second stop is 20 minutes.
STOP 2: Explore a few historic hot spots that contributed greatly to the Civil War. Perfect for the history buff in the group, with a few trails for the non-buff. Drive time to the third stop is 10 minutes.
STOP 3: We've recommended a charming street full of independent shops and local eateries. Into ghost stories? Stop off at a haunted museum. Drive time to the fourth stop is 15-25 minutes.
STOP 4: It's time to end the day your way! We've recommended a spooky cemetery, a winery with views, and a few more places to get your steps in.
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/haunts-hikes-history
- Charming CuriositiesNeeds location$65.00
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
