Asheville: Roaring ’20s Walking Tour with Drinks

If you’re heading to Asheville and want a different way to explore its lively history, the Roaring ’20s Walking Tour with Drinks might catch your eye. This experience promises a glimpse into the era when gangsters, speakeasys, and handcrafted spirits ruled the night, all wrapped up in a two-hour walk through Asheville’s charming historic district.

What we really like about this tour is how it combines storytelling with tasting. You get to learn fascinating tidbits about the 1920s while sipping on signature cocktails at different venues, adding a fun, tangible element to the history lesson. Also, the guide’s knowledge—especially if it comes from personal experience or local insight—can make all the difference, making the stories more engaging and authentic.

On the flip side, one potential consideration is that the tour is strictly for those aged 21 and over, which means no kids or pregnant travelers can join in on the fun. Plus, the review from a traveler who didn’t show up is a reminder that no experience is flawless, but it’s worth keeping in mind that the overall ratings are quite solid.

This tour really suits those who enjoy historical stories, craft cocktails, and a relaxed walk through a lively neighborhood. Whether you’re into history, architecture, or just looking to enjoy some local drinks while soaking up Asheville’s vibe, this experience could fit well into your trip.

You can check availability for your dates here:

Key Points

• Historical storytelling makes the experience engaging and informative
• Signature cocktails at each stop offer a fun tasting experience
• Short walking distance means it’s manageable for most travelers
• Knowledgeable guides add depth and entertainment
• Price point offers good value for the drinks and insights
• Limited to adults (21+) with no alcohol-free options

If you’re curious about how this tour stacks up, here’s a detailed walk-through of what you can expect.

The Concept and Overall Experience

This is a guided walking tour that lasts approximately 2 hours, making it a manageable activity if you’re tight on time or just want a quick, immersive experience. The tour takes you through some of Asheville’s most notable historic district venues, stopping at three different establishments renowned for their connection to the Prohibition era.

The focus is on history and culture of the 1920s, particularly how the city’s spirits scene evolved. The guide’s role is central—sharing stories, trivia, and anecdotes that bring the era to life. One reviewer mentioned that their guide, Don, was “knowledgeable (with firsthand experience as a child from his grandfather) and entertaining.” That kind of personal touch can truly elevate the experience, making history feel relevant and lively.

What Makes the Tour Special

The main draw is the combination of storytelling and tasting. Each stop offers a signature cocktail—a house specialty—which means you’ll get a taste of the era’s flavors. It’s a different experience from simply visiting a bar or tasting room; you get context, a story, and then a drink to match. It’s a laid-back way to “travel back in time,” especially if you’re into both history and mixology.

The tour also emphasizes Asheville’s history of handcrafted spirit production. If you’re into local craftsmanship, you’ll enjoy learning how the city’s spirits scene has evolved, tying modern craft drinks to their historic roots.

The Stops and Walk

The walk itself is about three blocks, so it’s quite manageable for most people. The venues are all popular spots within the historic district, which means you’re likely to be in a lively, atmospheric part of town. The walk is relaxed, with brief stops between venues, giving plenty of opportunities to chat with the guide or take photos.

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The Drinks and Atmosphere

You’ll sample three signature cocktails during the tour. These are house specialties, designed to evoke the spirit of the 1920s. While the specifics of each drink aren’t detailed, the experience promises a “full varied drinks” experience, which many find adds a lot of value. And it’s not just about drinking—it’s about understanding the culture, the ingredients, and the stories behind each sip.

The Guide’s Role

Most reviews highlight the guide’s knowledge and personality. For example, one reviewer said Don’s storytelling is both “knowledgeable and entertaining”, which is exactly what you want in a tour guide—someone who can make history memorable and fun without feeling like a history lecture.

What’s Not Included

The main thing missing is hotel pickup or drop-off, so you’ll need to plan your own transportation to and from the tour starting point. That’s fairly typical for walking tours but something to keep in mind if you’re staying outside the immediate downtown area.

Price and Value

At $99 per person, the tour isn’t the cheapest activity in Asheville, but it’s reasonable considering it includes three stops and three cocktails. If you’re into history, cocktails, or unique local experiences, this price can be quite justifiable. Plus, with the inclusion of a knowledgeable guide and the intimate setting, you’re paying for quality storytelling and a fun, relaxed atmosphere.

One thing to consider is that the tour is not suitable for pregnant women or those under 21, which is important if you’re traveling with family or friends who don’t drink.

The One Caveat

While the experience generally receives positive reviews, it’s worth noting that one traveler had a no-show incident. It’s a reminder to always confirm your booking and arrive on time, but with a 4.2-star rating from five reviews, most guests seem satisfied.

This experience is ideal for adults who enjoy history, cocktails, and a relaxed walking pace. If you’re curious about the local spirit scene or love stories from the Prohibition era, you’ll find this tour engaging. It’s also good for travelers who prefer a group activity that combines education with entertainment.

If you’re traveling with a group that includes non-drinkers, this might not be the best fit, given the age restrictions and alcohol-focused nature. But for those who want a fun, storytelling-heavy evening that offers a taste of Asheville’s historic nightlife, this really hits the mark.

The Asheville Roaring ’20s Walking Tour is a solid choice if you’re looking to pair local history with some fun sipping. The combination of knowledgeable guides, intriguing stories, and signature cocktails makes for an experience that feels both laid-back and engaging. While it might not be suitable for everyone—especially kids or non-drinkers—the tour’s managed pace and compact route make it accessible and enjoyable.

For those who appreciate authentic storytelling mixed with a bit of local flavor, this tour offers a memorable window into Asheville’s vibrant past. It’s particularly well-suited for history buffs, cocktail lovers, or travelers wanting a taste of the city’s lively, spirited side without leaving the downtown.

If you’re after a relaxed evening that blends education, local culture, and some good drinks, give this tour a serious thought. Just remember to book in advance, arrive on time, and enjoy your step back into the Roaring ’20s.

Is hotel pickup included?
No, the tour does not include hotel pickup or drop-off, so plan to meet at the starting point within walking distance of your accommodation.

Are children or anyone under 21 allowed?
No, this tour is strictly for those 21 and over, and pregnant women are also not suitable to participate.

How long does the tour last?
It lasts approximately 2 hours, making it a perfect short activity that doesn’t take up your whole afternoon.

What’s the walking distance?
The total walk is about three blocks, so it’s easy to manage for most travelers.

What should I bring?
Bring a valid ID or passport, as it’s required for age verification.

Is the tour accessible for people in wheelchairs?
Yes, the tour is wheelchair accessible, making it a good option for those with mobility concerns.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund, providing flexibility if your plans shift.

What’s the best way to dress?
Dress comfortably for walking, and consider bringing a small umbrella if the weather looks uncertain—it’s an outdoor-friendly tour.

The Asheville Roaring ’20s Walking Tour offers a fun, informative evening that combines local history with a taste of the era’s signature drinks. Whether you’re a history buff or just looking for a lively way to experience Asheville’s past, this tour might be just the ticket.

You can check availability for your dates here: