If you’re curious about Asheville’s vibrant past and want to experience its lively spirit from the Prohibition era, this Roaring ’20s walking tour might be just what you’re looking for. While we haven’t personally taken this tour, the details reveal an engaging blend of history, authentic storytelling, and delicious cocktails that can make for a memorable afternoon.
What really catches our eye is the emphasis on historical detail delivered by knowledgeable guides—like Don, who reportedly brings the era to life with firsthand stories. The tour’s inclusion of signature cocktails at three different venues, along with walking through Asheville’s charming historic district, offers a relaxed way to learn and indulge. Also, the tour’s focus on handcrafted spirits and local history makes it more than just a drinking experience; it’s a taste of Asheville’s unique past.
That said, one possible downside is the limited duration of just two hours—meaning the pace might be brisk, especially if you like to take your time. Also, since it’s a walking tour with some stops, those with mobility concerns should note the around three blocks of walking involved.
This tour suits travelers who enjoy history, cocktails, and lively storytelling, particularly those interested in the 1920s era or the city’s spirited past. It’s ideal for those seeking a fun, culturally rich experience that combines education with a social vibe.
Good To Know

- Authentic 1920s atmosphere created through storytelling and venue selection.
- Knowledgeable guides add depth and personal stories, making it more engaging.
- Signature cocktails at three historic Asheville venues enhance the experience.
- Walking through Asheville’s historic district allows for scenic and manageable exploration.
- Cost-effective at $99 for a two-hour experience including drinks and guided insights.
- Accessibility and timing are convenient, but consider walking distance and pace.
An In-Depth Look at the Asheville Roaring ’20s Tour

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The Concept and Overall Experience
This walking tour is designed to transport you back to a vivid era when speakeasies, gangsters, and jazz ruled the night. Over just two hours, you’ll cover about three blocks in Asheville’s historic district, hopping into three renowned venues. The aim is to give you a taste of what Asheville’s nightlife and social scene might have looked like during Prohibition—minus the risk, of course.
The tour’s blend of history, storytelling, and cocktails makes it appealing for those who love a bit of education with their socializing. It’s a relaxed, fun way to spend an afternoon or early evening, especially if you’re a fan of American history or craft cocktails.
The Itinerary and Venue Highlights
While the exact venues aren’t named in the provided info, we know you’ll visit three of Asheville’s most popular establishments in the historic district. These places are chosen for their historical significance and signature offerings, ensuring you get both a taste of the past and a sip of the present.
The stops are likely to be a mix of historic bars, possibly with a vintage vibe or a storied past. Each venue provides a unique atmosphere, whether it’s a cozy speakeasy-inspired bar or a lively historic tavern. The experience is designed to maximize your enjoyment of Asheville’s handcrafted spirits and signature cocktails—what better way to connect with the 1920s than with a well-made drink?
What You’ll Learn from the Guide
According to reviews, guides like Don stand out for their wealth of knowledge and ability to entertain. One reviewer mentions that Don shares stories from his grandfather, giving the tour an authentic and personal touch. The guide’s role is crucial in making the experience both informative and amusing, filling in historical gaps with engaging trivia and local insights.
You’ll hear about the city’s secret speakeasies, the gangsters of the era, and the rise of Asheville’s craft spirit scene. Expect lively narratives that reveal the city’s unique history of handcrafted spirit production, which remains a point of pride for Asheville even today.
More Great Thing To Do NearbyTasting the Signature Cocktails
Each stop offers a distinctive house specialty, giving you a taste of what inspired bartenders of the era. These drinks are part of the fun, allowing you to sample local twists on classic cocktails, or perhaps even signature creations that reflect Asheville’s spirit scene.
One reviewer highlights the importance of pacing yourself with the drinks, noting “if you have low tolerance: pace yourself!” which is a good tip for enjoying the experience without feeling overwhelmed. The included three signature cocktails are a highlight, blending history and flavor in every sip.
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Practical Details and Considerations
The tour costs $99 per person, which, when you consider the guided storytelling, three drinks, and walking exploration, offers good value. The two-hour duration makes it a manageable activity, especially in the afternoon, leaving you room for other explorations afterward.
Since the walking distance is only around three blocks, and the pace is generally light, most people should find it accessible. However, it’s worth noting that pregnant women and those under 21 are not suitable for this experience, primarily due to the alcohol component.
No hotel pickup or drop-off is included, so plan to meet at the designated starting point in Asheville’s historic district. It’s also wheelchair accessible, which broadens its appeal.
What Real Participants Said
One reviewer expressed disappointment about a no-show incident, which highlights the importance of confirming your booking. On the positive side, another reviewer raves about Don’s storytelling, describing him as “knowledgeable and entertaining”. The mix of reviews reminds us that the experience’s quality heavily depends on the guide and the execution.
Final Thoughts

This Roaring ’20s walking tour in Asheville offers a lively combination of history, local culture, and crafted cocktails. It’s best suited for those with an interest in American history, vintage atmospheres, or simply those looking for a fun and engaging way to explore Asheville’s historic district.
The tour’s price point reflects its value—especially with three curated stops and expert storytelling—that make it more than just a drinking session. The relaxed, manageable walking pace and the inclusion of signature drinks make it accessible for most visitors.
However, it’s essential to consider the pace and walking involved, especially if mobility is a concern. It’s also worth booking in advance to avoid disappointment—based on the mixed reviews, reliability can vary.
In essence, this experience is a perfect fit for history buffs, cocktail lovers, and travelers eager to embrace Asheville’s unique past in a fun, social setting. It stands out as a distinctive way to uncover the city’s lively 1920s scene without the hassle of planning individual stops or navigating unfamiliar venues.
FAQs

Is hotel pickup included?
No, the tour does not include hotel pickup or drop-off. You’ll need to meet at the designated starting point within Asheville’s historic district.
How long is the walk?
The total walking distance is around three blocks, making it a short and manageable stroll through Asheville’s historic area.
Are the drinks included in the price?
Yes, the tour includes three signature cocktails, one at each stop, allowing you to sample local and period-inspired drinks.
Is the tour accessible for people with mobility issues?
The tour is wheelchair accessible, but since it involves walking around three blocks, consider your mobility comfort before booking.
What is the age restriction?
This experience is not suitable for those under 21 or pregnant women, due to the alcohol consumption involved.
Can I cancel or reschedule my booking?
Yes, you can cancel up to 24 hours in advance for a full refund. You also have the option to reserve now and pay later for flexibility.
What kind of venues do we visit?
While specific venues aren’t named, expect to visit three popular establishments in Asheville’s historic district, selected for their historical significance and signature cocktails.
Who are the guides?
Guides like Don are known for their engaging storytelling and deep knowledge—one reviewer notes he shares personal stories from his grandfather’s experiences.
What makes this tour different from others in Asheville?
It’s focused on the Prohibition era, combining history, authentic venues, and signature cocktails in an intimate walking experience.
Would this be a good night activity?
Yes, especially in the late afternoon or early evening, to enjoy a relaxed atmosphere with drinks and stories in historic Asheville.
This Roaring ’20s walking tour in Asheville offers a compelling mix of history, local flavor, and social fun. It’s perfect for travelers who want to get a sense of Asheville’s past while enjoying crafted cocktails in a relaxed setting. The guided storytelling ensures you’re both entertained and informed, making it a worthwhile addition to your Asheville itinerary.
The experience is most suited for those interested in history, vintage aesthetics, and small-group socializing. While the two-hour format and walking distance are manageable for most, it’s worth considering mobility and pace preferences. The inclusion of three signature cocktails at historic venues makes the price competitive, especially given the expert guides and enriching stories you’ll hear.
This tour delivers a lively, educational, and flavorful glimpse into Asheville’s spirited 1920s scene—an experience worth considering if you’re in the city and want to experience its historical nightlife in a fun, authentic way.
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