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These Winston-Salem tours go way beyond the usual, from hidden history to haunted alleyways. You’ll never look at the Twin City the same way again.
Whether you’re a first-time visitor with fresh eyes or a lifelong local craving something new, these unforgettable tours peel back the layers of the city like the pages of a well-loved book. One minute, you’re gliding down the Strollway on a Segway; the next, you’re sipping Southern bites in a secret courtyard or listening for whispers of the past under lantern light.
These aren’t your average sightseeing tours. They’re memory makers. Ghost stories and garden strolls. Paddleboards and pastries. Horse-drawn carriages and candlelit whispers. Each one invites you to slow down, look closer, and fall in love with the magic woven into every cobblestone and café.
So grab your walking shoes (or your sense of adventure) and explore Winston-Salem in ways you never imagined.
Step Into the Stories of Winston-Salem: Top Tours That Bring the City to Life
Every city has its secrets. But Winston-Salem wears its past like perfume: subtle, layered, and unforgettable. You’ll catch it in the scent of fresh-baked Moravian cookies drifting from a bakery window, the creak of antique floorboards beneath your feet, and the flicker of a lantern cutting through dusk on a haunted street corner.
Winston-Salem isn’t just a place you pass through. It’s a place you feel.
What is the best way to experience it? Let someone show you. Someone who knows the stories etched into the bricks, the legends whispered under breath, the hidden spots where time seems to pause.
These tours aren’t just activities. They’re invitations. To connect, remember, and fall in love with a city you thought you already knew or maybe didn’t know at all.
So whether you’re here for a weekend or a lifetime, here are the top Winston-Salem tours that will surprise, delight, and maybe even send a chill down your spine. Let the exploring begin.
1. Reynolda House: Where Art, Gardens, and History Bloom
If the walls of Reynolda House could talk, they’d have a century’s worth of stories to whisper.
Once the grand estate of R.J. and Katharine Reynolds, this magnificent property just northwest of downtown is now one of Winston-Salem’s crown jewels. Owned and managed by Wake Forest University, Reynolda offers a rich blend of art, architecture, and garden serenity, making it a favorite for visitors and locals alike.
Inside Reynolda House
Step into the past and discover:
- More than 6,000 historic objects, from heirloom furniture to decorative arts.
- A world-renowned American art collection featuring pieces by Georgia O’Keeffe, Grant Wood, and other iconic artists.
- The Babcock Gallery showcases rotating exhibitions that highlight both contemporary and historical works.
Outside the House
Let the gardens and grounds draw you in with the following:
- Formal gardens are arranged in classic designs, often bursting with color during spring and summer.
- Greenhouses, wooded walking trails, and tranquil spots are ideal for quiet reflection.
- A peaceful, 16-acre artificial lake that reflects the changing seasons.
- A golf course for those looking to combine culture and leisure.
Whether you’re drawn to the art, the gardens, or simply the feeling of stepping into another era, Reynolda offers an experience that feels both timeless and unforgettable.
Visit the Reynolda website for tour details, seasonal events, and exhibition schedules. Many popular events and gallery shows fill quickly, so plan ahead if you can.
2. Old Salem Museum & Gardens: Step Into the 18th Century
Old Salem Museums & Gardens offers a living history experience unlike anything else in the region. It’s a lovingly restored Moravian settlement where costumed interpreters, working tradespeople, and authentic architecture bring early Southern life vividly to life. This is not just a walk back through history. It’s a walk inside it.
What You’ll See and Do
- Explore restored homes, churches, and shops dating back to the 1700s.
- Watch live demos from tinsmiths, tailors, and traditional bakers.
- Visit Winkler Bakery, where the scent of fresh bread fills the air just as it did two centuries ago.
- Wander through heirloom gardens and charming cobblestone paths.
- Learn about the roles of enslaved and free African Americans who shaped this community.
Details:
- Open Wednesday to Saturday, 10:00 a.m. – 4:00 p.m. (excluding special events; seasonal hours may vary)
- Options for self-guided or interpreter-led tours.
- Admission fees vary by experience (discounts available).
- Tickets can be purchased onsite or ahead of time online.
Whether you’re a history buff or just love immersive storytelling, Old Salem turns a day trip into a time machine.
3. Carriage Rides Through Old Salem: A Step Back in Time
There’s something undeniably magical about the soft clip-clop of hooves on historic cobblestone. For a truly charming and nostalgic way to explore Winston-Salem, a horse-drawn carriage ride through Old Salem delivers the whole storybook experience.
Offered by Heritage Farm & Carriage, this tour blends history with romance, letting you slow down and see the city from a new perspective that echoes centuries past.
What to Expect
- A private, 45-minute narrated carriage ride through the historic Old Salem district.
- Custom commentary that weaves together local stories, landmarks, and lesser-known facts.
- A beautifully restored carriage that comfortably seats four adults and two small children.
- The peaceful rhythm of horses guides you through one of the city’s most iconic neighborhoods.
- Price: $250 per ride, plus gratuity
- Booking: Call 336-784-8419
This experience is available by appointment only and tends to be booked quickly during peak seasons, holidays, and special events. For more information, visit the Heritage Farm & Carriage Facebook Page
Whether you’re celebrating something special or simply want to see Old Salem in a new light, this ride offers a moment of calm, connection, and old-world beauty.
4. Segway Tours with Triad Eco Adventures: Glide Through History, Mystery, and Modern Charm
Winston-Salem isn’t just a city to walk through. It’s a city to glide through. With Triad Eco Adventures’ Segway tours, you can cover more ground without breaking a sweat and see the city from a fresh, fun, and eco-friendly perspective.
These aren’t your average sightseeing jaunts. From scenic greenways to spine-tingling tales of the city’s past, each route offers a different lens through which to experience Winston-Salem’s layered personality.
Tour Options Include
- A mini orientation and glide along the Greenway and Strollway, perfect for beginners (minimum of 3 participants required).
- A two-hour downtown tour that highlights Winston-Salem’s historic and modern heart.
- A UNCSA and Washington Park route showcasing architecture, creativity, and quiet green spaces.
- A two-hour Old Salem and Salem College tour (offered on Mondays only) for a deep dive into early Moravian life.
- The Mayhem & Mystery Tour focuses on chilling historical tales and odd true stories.
- Seasonal and specialty routes, including:
- African American History Tour
- Night Lights Tour (for experienced Segway riders only)
Additional custom tours are available by request.
Booking and Rates:
- Mini-tour with orientation: $42
- Two-hour tours: $89 for 1–2 people, with lower rates for larger groups
- Gratuities not included
- Reservations: Call 336-722-7777 or visit the Triad Eco Adventures website
From leisurely glides past historic facades to eerie tales told at twilight, these Segway tours are an innovative, stylish way to roll through the city’s highlights, with a breeze on your face and a story around every corner.
We Rolled Through Winston-Salem on a Segway and Loved Every Minute
We tried the Segway tour with Triad Eco Adventures ourselves, and it was one of the most unexpectedly fun ways to explore downtown Winston-Salem. Here’s what stood out during our ride and what you’ll definitely want to know before hopping on.
Several years ago, I did the Segway tour with Triad Eco Adventures in exchange for an unbiased review. It was a fun and unique way to make our way around downtown and experience the hills without quite as much effort.
But, I must say, your calves will likely be sore after this experience, even if you are fit, because it uses your muscles in a way that is different from most other activities. Our tour guide called this “Seg Leg,” and we were encouraged to stretch at every stop.
Aside from that, I would highly recommend this for clients with good balance – knowing how to ride a bike is likely enough to help you be successful and enjoy the tour.
– Michelle Schenker, Winston-Salem Native & Website Co-Founder
5. African-American Heritage Tours: Hidden History, Bold Stories
Winston-Salem’s Black history runs deep; many of its most powerful stories aren’t found in textbooks. These Winston-Salem tours center on the voices and legacies of African Americans who helped shape the city through art, business, education, and resilience.
Highlights May Include
- Depot Street and the historic African-American commercial district.
- Legacy landmarks of Winston-Salem State University (WSSU), one of the nation’s oldest HBCUs.
- Black-owned businesses and historically significant churches.
- Cultural narratives from Reconstruction to the Civil Rights era.
Triad Cultural Arts Tours: Exploring Winston-Salem’s African American Legacy
Winston-Salem’s story isn’t complete without the voices, resilience, and cultural contributions of its African American community. Triad Cultural Arts offers an immersive and educational look into this vital part of the city’s identity through walking, bus, trolley, and even virtual experiences.
These Winston-Salem tours invite both individuals and groups to explore the people, places, and legacies that shaped the city. From historic churches and neighborhoods to public art and NC’s first urban Rosenwald School, this is more than sightseeing. It’s a cultural deep dive into the heart of Winston-Salem.
Tour Locations May Include:
- Historic African American neighborhoods and landmarks
- Art galleries, sculpture gardens, and public art installations
- Churches, educational institutions, and civil rights sites
- The former Black Business District in East Winston and the Innovation Quarter
- A scavenger hunt designed to engage while educating
Walking Tour (Individual Option)
Perfect for solo travelers or small groups seeking a conversational, ground-level experience.
- Explore Downtown, East Winston, and the former Black Business District
- Guided walk-and-talk format, approx. 1–1.5 hours
- Price: $25 per person
Trolley & Bus Tours (Group Options)
Designed for larger groups looking to learn together in comfort.
- Narrated tours with engaging guides and QR code-enhanced content
- Approx. 2 hours in duration
- Trolley Tour: $59 per person (28–29 guests)
- Bus Tour: $55 per person (minimum of 20 guests)
Step-On Tours (Private Groups)
Ideal for custom group experiences, whether using your own vehicle or a rental.
- A Triad Cultural Arts guide joins your group to provide expert insights
- Approx. 2 hours
- Rates: $400 for up to 20 people, $500 for groups of 20–48
360° Virtual Tour
Don’t let distance keep you from the experience. This virtual option makes cultural discovery accessible from anywhere.
- Explore exhibits, artwork, and historical narratives online
- Cost: $10 per person (minimum 10 guests)
All tours can be reserved online through the Triad Cultural Arts website. Whether you’re local or visiting, these Winston-Salem tours offer a meaningful way to connect with the city’s deeper roots and walk away with a fuller understanding of the stories that still shape it today.
Other Options
- Triad Eco Adventures offers a guided African-American History Segway Tour.
- Seasonal or community-led walking tours may be available during Juneteenth, Black History Month, or city festivals.
- Self-guided options using online walking maps or local archives.
A vital addition to any trip, these tours honor the strength, artistry, and perseverance of Winston-Salem’s Black community, past and present.
6. Food Tours in Winston-Salem: Taste Your Way Through the City
Some cities tell their stories through statues and plaques. Winston-Salem tells hers through flavor. Join one of the city’s downtown food tours and discover the culinary soul of Winston-Salem, bite by bite.
These walking tours guide you through the heart of downtown, with stops at beloved local restaurants, cozy cafés, upscale kitchens, and maybe even a surprise hole-in-the-wall or two.
You’ll meet the chefs, hear the backstories, and, most importantly, sample the goods.
It’s more than just a meal. It’s a moving feast, a walking history lesson, and a local love letter all in one.
Taste Carolina Gourmet Food Tours
If brunch is your love language, this one’s for you.
Taste Carolina’s Winston-Salem brunch tour is a standout experience that takes you from the charming West End to the energetic 4th Street district. Along the way, you’ll enjoy generous tastings paired with local beverages while learning how chefs and owners craft their menus around seasonal, locally sourced ingredients.
What’s Included:
- A guided walking tour through key downtown neighborhoods
- Stops at multiple eateries, ranging from modern Southern restaurants to time-tested local favorites
- Brunch tastings paired with handpicked drink offerings
- Stories behind the food, the chefs, and the neighborhoods themselves
Details:
- When: Saturdays at 10:45 am
- Duration: Approximately 3 hours
- Price: $79 per person, plus a $6 ticketing fee
- Reservations: Book through their online calendar
Whether you’re a foodie looking for your next favorite dish or a visitor hoping to eat like a local, this tour delivers an experience that’s warm, welcoming, and utterly delicious.
7. Paddleboard Lessons & Tours: Find Your Balance on Salem Lake
Think Winston-Salem is all gardens and galleries? Think again. Sometimes, the best view of the city is from the water, with a paddle in hand and sunlight dancing across the lake.
Triad Eco Adventures offers guided stand-up paddleboarding (SUP) lessons and tours on beautiful Salem Lake, just minutes from downtown. Whether you’re a first-timer or have a decent balance, thanks to years of yoga, this experience blends outdoor adventure with peaceful scenery and just the right amount of thrill.
What the Experience Includes
- A 1-hour and 45-minute session combining both instruction and a relaxing tour of the lake.
- A beginner-friendly lesson to get you standing, paddling, and maybe even striking a triumphant pose.
- A guided lake tour with stories, tips, and views you can’t get from shore.
- The option to stay dry if you listen to your instructor (but getting wet is half the fun).
Booking and Pricing:
- $89 per person for a group of two
- Lower per-person rates are available for larger groups
- Gratuities not included
- Reservations required
The season begins in March.
Visit the Triad Eco Adventures website to check availability and book your tour. This is one of those rare experiences that leaves you both energized and centered. Paddleboarding on Salem Lake feels like a mini vacation without ever leaving town.
8. e-Bike Tours: Effortless Exploration on Two Wheels
Craving fresh air and new views but not the uphill struggle? An e-bike tour with Triad Eco Adventures lets you breeze through the best parts of Winston-Salem while still soaking in the sights.
These guided rides combine the ease of electric bikes with curated city and nature routes. Whether you’re winding past downtown architecture or cruising toward Quarry Park’s panoramic overlook, these tours are built for both adventure and comfort.
Tour Options
- Starts at Gateway, 176 YMCA Way
- Pedal along the Greenway, through Old Salem and Innovation Quarter, circling downtown.
- The narrated experience is rich in local history and modern highlights.
- A nature-focused escape
- It passes Salem College, Winston-Salem State University, a scenic golf course, and ends with stunning views at Quarry Park.
Details:
- Duration: 2 hours
- Age Requirement: 16 and up
- Group Size: Minimum of 2 people
- Price: $89 per person, with lower rates for larger groups
- Gratuities not included
- Reservations: Visit the Triad Eco Adventures website
For city lovers and trail chasers alike, this tour offers a chance to see Winston-Salem with a bit of zip and no sweat.
9. Ghost Tours: Haunted Histories and Lantern-Lit Streets
If you feel a chill down your spine on a warm evening in Winston-Salem, you might be walking in ghostly company. The city’s long, layered past makes it a prime setting for haunted tales, and these guided ghost tours know just where to look (and listen).
Carolina History & Haunts: West Endings
This popular walking tour by lantern light explores the city’s historic West End district, where mystery and memory intertwine. Put on by Carolina History & Haunts, the tour is held year-round and explores the historic West End district by lantern, featuring tales of “love, money, and a few unfortunate endings.”
You’ll hear stories of:
- Lost love, tragic accidents, and inexplicable encounters.
- Superstitious customs and cultural lore still linger in Winston-Salem.
- Former residents who never quite moved on.
Tour Info:
- Duration: 90 minutes
- Price: $20 for adults, $15 for children ages 7–12, and free for kids 6 and under
- Details & Tickets: Call 833-628-6277 or visit the Carolina History & Haunts website
Tours meet in the courtyard behind The Rosenbacher House. This is also the home of Boutique Wellness/Wines and The Manolo Cafe. 848 West Fifth Street, Winston-Salem. For information, call 833-628-6277.
Night Watchman Tours (October Only)
Offered Thursday through Saturday during the spooky season, this candlelit walk through Old Salem immerses you in the darker side of local history.
What makes it special:
- Led by a costumed Night Watchman on his “rounds.”
- Real historical events with documented paranormal activity.
- Chilling tales are set in historic buildings and eerie corners.
Tour Info:
- Season: Mid-October through Halloween
- Age Limit: Guests 10+ only; under 18 must be accompanied by an adult
- Duration: Approximately 1 hour
- Price: $50 per person (subject to change)
- Booking: Reserve Night Watchman Tours as the season approaches
10. Winston-Salem Walking Tours: True Crime & Hidden History
Winston-Salem’s past isn’t all polished charm. Beneath the surface lie tales of crime, chaos, and fascinating contradictions. These walking Winston-Salem tours dig deeper into the city’s beauty and darker corners.
True Crime Tours
Meet your guide outside Fair Witness Fancy Drinks, 290 E 4th Street, Winston-Salem (a great place to have a drink after your tour!), and prepare to hear the city’s most disturbing real-life crime stories.
Highlights include:
- Strange and unsettling tales from Winston-Salem’s history.
- Visits to real locations are tied to each story.
- A mix of suspense, history, and old-fashioned curiosity.
Details:
- When: Saturdays at 4 pm
- Price: $19 per person
- Reservations: Visit Get Your Guide True Crime Tour
Downtown Winston-Salem Historic Guided Tour
This one-hour stroll dives into the forces that shaped the city into a Southern success story.
What you’ll learn:
- How Winston-Salem rose to national prominence in industry and innovation.
- Architectural secrets, including the inspiration behind the Empire State Building.
- Prohibition-era stories, including moonshine routes and hidden speakeasies.
- The tour is based on research by a professional historian.
Details:
- When: Saturdays at 2 pm
- Meeting Spot: Fair Witness Fancy Drinks, 290 E 4th Street
- Price: $19 per person
- Booking: Available through Get Your Guide
11. Christmas Tours: Holiday Magic in Motion
When the holidays roll in, Winston-Salem transforms into something straight out of a snow globe. The lights twinkle. The cocoa flows. And yes, there are tours for that, too.
From candlelight strolls through Old Salem to downtown light displays and historic homes decked in evergreen, Christmas in Winston isn’t just festive. It’s immersive.
Many tours sell out quickly during the holiday season.
The best way to stay in the loop is to check our Winston-Salem Christmas Lights & Activities Guide. Whether you want nostalgia, family fun, or a peaceful winter walk, there’s something magical waiting.
Did we miss your favorite local tour? Or maybe you had a memorable moment on one of these adventures? We’d love to hear about it. Share your Winston-Salem tours and stories in the comments.
Your Next Winston-Salem Adventure Starts Here
Ready to see the city in a whole new light? These Winston-Salem tours are just the beginning of what the Twin City has to offer. From ghost stories whispered beneath gaslight to paddleboard reflections on a quiet lake, Winston-Salem invites you to experience the city, not just see it. Whether you’re chasing history, flavor, or just a new perspective, you’ll find it here.
But don’t stop exploring just yet.
Once you’ve had your fill of guided tours, there’s still plenty more to discover.
Stretch your legs on one of our favorite walking trails in Winston-Salem, from shady creekside paths to urban greenways. Plan a weekend escape with one of these unforgettable day trips from Winston-Salem. Or scroll through our local guide to the best things to do in Winston-Salem, from live music and vendor markets to rooftop drinks and historic strolls. Winston-Salem has a way of surprising you. So take your time. Try something new. And let the city show you what it’s made of.
