Highlights of Winston-Salem: A Tobacco Trail
4.8561 Reviews155 people have played this questFollow clues and solve challenges to unlock local stories. See famous landmarks and not-so-famous hidden gems. Learn about the New South's industrial rise. And have fun solving puzzles!
Note: Ideal parking is along Main Street between 1st and 4th. Tour is best done during the day.
How many are playing?
Unlock · $9.99Live in Winston-Salem? The Annual Pass is how locals play · $79.99/yr. See the Annual Pass →
Places you will visit
12
It will take you
98-128 mins
You will walk
2760 steps
Total distance
2.1 km
What you'll actually do
Download the Questo app and unlock the quest. Walk to RJ Reynolds Statue whenever you like · no guide, no group, no time slot.
Solve 12 puzzles hidden in the streets around you. Each one you crack unlocks the next location.
Finish at Reynolds American and see where you land on the Winston-Salem leaderboard.
Highlights
Discover the most important leaf in Carolina history.
Uncover the rebel legacy of Bailey Park.
Explore the disappeared Depot Street neighborhood.
Learn who won downtown's Race to the Sky.
Grab a drink in 1929's Best New Building of the Year.
Landmarks & Hidden Gems Included
The Depot Street Mural
The Bailey Brothers Factory
The Nissen Building
The R.J. Reynolds Statue
Ratings and Reviews
61 ratings
Andrew Jones
Diane Goldstein
Lgm5214
Kristin95
Sheena
A note from Jacqlyn Phillips
“Jacqlyn is a writer based in North Carolina. She loves exploring the frontiers of storytelling and hopes you enjoy her Questo game!”
The mission: Your story in Winston-Salem
You're the Chief of Salem's Rough and Ready Fire Company—and a fire is afoot!
The bells are sounding in every district, smoke is filling the streets. But strangely, the source of the fire is completely unknown.
Your job, Chief, is to track it down.
Find that fire before it spreads and save your beloved Camel City.
There's no time to spare. Grab your trustiest steed and ride!
Heeyah!
Beat the best: Top Winston-Salem explorers
Good to know before you play
- We recommend not playing at night
- No attractions ticket(s) required
Compare Questo vs. Guided Walking Tours
Flexibility
Regular Guided Tours
Fixed schedules & no pausing
Questo
Start, pause, and resume anytime
Privacy
Regular Guided Tours
Crowds of up to 30 strangers
Questo
Private experience for your group only
Pricing
Regular Guided Tours
$30–$60 (€23–€50) per person
Questo
Transparent pricing shown before checkout
Availability
Regular Guided Tours
Requires advance booking
Questo
Instant access 24/7/365
Experience
Regular Guided Tours
Passive listening to a guide
Questo
Active gamification; you solve the mystery
| Feature | Regular Guided Tours | Questo |
|---|---|---|
| Flexibility | Fixed schedules & no pausing | Start, pause, and resume anytime |
| Privacy | Crowds of up to 30 strangers | Private experience for your group only |
| Pricing | $30–$60 (€23–€50) per person | Transparent pricing shown before checkout |
| Availability | Requires advance booking | Instant access 24/7/365 |
| Experience | Passive listening to a guide | Active gamification; you solve the mystery |
Joined by 1,000,000+ explorers worldwide
Guided tour pricing: Comprehensive Economic Analysis of Guided Tour Pricing, EU and US markets, 2026. Standard 2–3 hour group walking tours.
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EXPLORE WINSTON-SALEM ON FOOT
A flexible self-guided way to discover Winston-Salem
Highlights of Winston-Salem: A Tobacco Trail is for travelers who want a private, self-guided city experience rather than joining a scheduled walking-tour group. You follow a route, solve clues and discover places at your own pace.
The route starts at RJ Reynolds Statue and finishes at Reynolds American over 2.1 km, with 12 challenge locations. Typical duration: 113 min; 2.1 km walking route; 12 challenge locations
Choose this for flexibility, privacy and active discovery. Choose a guided walking tour when live commentary and asking a guide questions matter more. Playable languages: English.
