Asheville Tail of the Dragon and Cherohala Skyway Weekend Tour

A Two-Day Motorcycle Adventure Through the Mountains: Asheville to Tail of the Dragon & Cherohala Skyway

If you’re craving a motorcycle journey that combines challenging curves, breathtaking mountain views, and charming mountain towns, the Asheville Tail of the Dragon and Cherohala Skyway Weekend Tour might just be your ticket. Starting from Asheville, North Carolina, this $450 tour offers a roughly two-day escape that promises 318 curves, scenic vistas, and an authentic riding experience. Led by friendly guides, you’ll weave through some of the most iconic routes in the southeastern U.S., enjoying a balance of thrill and tranquility.

What we love about this tour is how it balances the adrenaline of the winding roads with the serenity of mountain scenery — perfect for those who love a bit of challenge but also want to soak in the landscape. Another highlight is the opportunity to visit charming small towns, where you can stretch your legs and grab a bite, adding a touch of local flavor to your adventure.

A possible consideration is that this tour is geared toward moderately fit participants who are comfortable on a motorcycle for extended periods. Also, since the ride depends on good weather conditions, those planning for a specific weekend should be aware of potential cancellations due to poor weather.

This experience is ideal for motorcycle enthusiasts, adventure seekers, and those wanting a scenic weekend getaway with a sense of camaraderie and excitement. If you’re looking for a memorable ride with a comfortable group size, this tour offers genuine value.

Key Points

• Scenic Routes: Motorcycle routes include the famous Tail of the Dragon with 318 curves and the Cherohala Skyway, both offering stunning mountain views.
• Two-Day Itinerary: Combines riding and sightseeing, with an overnight stop at the Deals Gap Motorcycle Resort.
• Group Size & Comfort: Limited to 9 travelers, perfect for personalized guides and fewer crowds.
• Weather Dependence: The tour operates only in good weather; cancellations are possible if conditions worsen.
• Pricing & Value: At $450 per person, it offers a well-rounded experience that balances thrill, scenery, and local culture.
• Booking & Cancellation: Flexible cancellation policy—full refund if canceled 6 days in advance.

The Detailed Experience

Starting in Fairfax, Virginia, the tour kicks off with a meeting at Patriot Harley Davidson around 4:00 pm, giving you a chance to settle in and meet your fellow riders. The journey truly begins the next morning, with an early departure from Asheville, around 9:00 am. As you leave the city behind, you’ll head west via I-40 and US-74, a comfortable start before the real fun begins.

Day 1: From Asheville to Bryson City

The first highlight is arriving in Bryson City, North Carolina, around 10:30 am. This small mountain town offers a tranquil setting to take a quick break, stretch, and prepare for the winding roads ahead. We appreciated how the tour smoothly transitions from urban to rural, setting the tone for the riding days to come.

Day 2: The Heart of the Ride—Tail of the Dragon & Cherohala Skyway

After a hearty breakfast at the Deals Gap Motorcycle Resort—a hub for bikers and a great place to soak in the local motorcycle culture—the group departs around 9:00 am. Here, you’ll start riding the Tail of the Dragon, famous for its 318 curves in 11 miles. This stretch is a must-ride for motorcycle enthusiasts, offering a challenging yet incredibly scenic experience. As one rider put it, “We loved the way the curves kept coming — it’s a real test of your riding skills but incredibly fun.”

Following that, you’ll head towards the Cherohala Skyway, a mountain pass that offers sweeping views and a more relaxed pace. The route combines twisting mountain roads with panoramic vistas, making it a favorite among those who love nature and open-air riding. The transition from the tight curves of the Dragon to the sweeping curves of the Skyway provides a balanced riding experience.

What You Can Expect

The tour usually takes about 2 days, with ample time to enjoy each stop without feeling rushed. The group size of up to 9 riders means you’ll get more personalized attention from guides and a friendly atmosphere. The mid-morning departure and targeted stops make for a manageable day, even for riders newer to mountain roads.

Experience & Authenticity

Riders have shared that the tour feels well-organized, with guides often sharing local tips and insights about the areas. The mountain views are consistently praised, and many mention the thrill of tackling the curves with professional guidance. The small group size fosters camaraderie, making even solo travelers feel welcomed.

Practical Considerations

Since the tour is dependent on good weather, travelers should check the forecast before booking. The moderate physical fitness level required is mostly about being comfortable on a motorcycle for several hours, including some tight turns and elevation changes. The price reflects the guided nature, scenic routes, and small group intimacy, offering good value for those seeking a dedicated motorcycle adventure.

Who Will Love This Tour?

This trip is best suited for motorcycle riders who enjoy scenic mountain roads and are comfortable with winding routes. It’s perfect if you want a guided experience that combines adventure with camaraderie. Those interested in small-group tours will appreciate the personal attention, while adventure lovers will relish the challenge of the curves.

It’s also a good fit for enthusiasts wanting to visit iconic routes in the Southeast, and for riders who value authentic motorcycle culture—the stops at biker-friendly spots like Deals Gap are a highlight.

Why Choose This Tour?

The value comes from combining professional guidance, well-planned routes, and a comfortable group size into one package. Compared to planning your own route, this tour saves you the hassle of navigation and coordination, letting you focus on the riding and scenery. Plus, the overnight stay at a dedicated motorcycle resort adds to the experience, giving you a chance to relax and share stories with fellow riders.

It’s particularly appealing for those who want a structured weekend that balances riding, sightseeing, and socializing, all within a manageable price point.

Final Thoughts

If you’re looking for a well-organized motorcycle adventure that takes you through some of the most scenic and exciting routes in the southeastern United States, this Tail of the Dragon and Cherohala Skyway tour offers great value and authentic experience. It combines thrilling curves, mountain vistas, and small-group camaraderie into a memorable two-day journey.

While it’s best suited for riders comfortable on mountain roads and seeking guided support, even seasoned motorcyclists will find plenty to enjoy here. The tour’s flexible cancellation policy also makes it a relatively low-risk way to explore this iconic route, weather permitting.

For anyone dreaming of a motorcycle escape that mixes adventure with the charm of mountain towns, this tour will deliver on all counts—an ideal choice for a weekend ride that leaves lasting memories.

FAQ

Is this tour suitable for beginner riders?
This tour is best suited for riders with a moderate physical fitness level and some experience with mountain roads. The emphasis is on curves and elevation changes, so comfort on winding roads is important.

What’s included in the price?
The tour price covers guided riding, group coordination, and the overnight stay at the Deals Gap Motorcycle Resort. Details about food or additional expenses aren’t specified but are typically on your own.

Can I cancel if the weather looks bad?
Yes, cancellations are allowed up to 6 days in advance for a full refund. The tour is weather-dependent, and poor conditions may lead to cancellations or rescheduling.

How many people will be in my group?
The maximum group size is 9 travelers, which helps ensure a more personalized experience.

Where does the tour start and end?
It begins at Patriot Harley Davidson in Fairfax, VA and ends back at the same location, following the two-day route.

Is there any flexibility in the itinerary?
The itinerary is pre-planned but might vary slightly depending on weather and group pace. The focus is on the rides and scenic stops.

What should I bring?
Participants should be prepared for riding in mountain weather, possibly including rain. A moderate physical fitness level and proper riding gear are recommended.

Is this experience suitable for non-riders?
No, this is a motorcycle-focused experience requiring participants to ride their own or guided bikes. Spectators or passengers would need to book a separate experience.

If you’re ready for a weekend of winding roads, mountain views, and biker camaraderie, this Tail of the Dragon and Cherohala Skyway tour offers a genuine slice of motorcycling heaven.