Asheville Tail of the Dragon and Cherohala Skyway Weekend Tour

Planning a motorcycle trip that balances adrenaline, scenery, and a touch of Southern charm? This two-day tour from Asheville, North Carolina, through the famous Tail of the Dragon and the breathtaking Cherohala Skyway promises just that. While we haven’t personally taken this ride, the itinerary and reviews paint a picture of a well-structured adventure for motorcycle enthusiasts and scenic road lovers alike.

What we love about this tour is its focus on classic North Carolina mountain roads—those 318 twists and turns on the Tail of the Dragon alone make it a bucket-list ride for many. Plus, the inclusion of the Cherohala Skyway, known for its sweeping vistas and less crowded routes, broadens the scenic appeal. A possible downside? The pace can be intense if you’re not accustomed to mountain riding; this trip is best suited for those with moderate physical fitness and riding experience.

This tour would suit motorcycle enthusiasts craving a structured, guided experience that hits some of the most famous mountain roads in the eastern U.S., while also allowing for some relaxed moments in charming towns. It’s perfect for groups of up to nine riders who want a mix of thrill and scenic beauty, all wrapped in a manageable two-day format.

Key Points

• Focus on iconic roads: Ride the legendary Tail of the Dragon and Cherohala Skyway, known for their curves and vistas.
• Well-organized itinerary: From Asheville to Bryson City and Deals Gap, with planned stops and scenic breaks.
• Group size: Limited to nine riders, fostering a more personal experience.
• Cost vs. value: At $450 per person, you gain access to some of the best motorcycle roads in the U.S. with guided support.
• Weather considerations: The tour is weather-dependent; poor conditions may lead to cancellations or rescheduling.
• Meeting point: Starts at Patriot Harley Davidson in Fairfax, VA, with the activity ending back at the start.

An In-Depth Look at the Experience

Starting Out in Asheville

The adventure kicks off with a pickup at Patriot Harley Davidson in Fairfax, VA, at 4:00 PM. Although this may seem distant from Asheville, the tour essentially begins with the ride to North Carolina. The focus is on hitting the road early the following morning, around 9:00 AM, heading west along I-40 and US-74 toward Bryson City. This part of the journey is about setting the tone—anticipating the twisty, scenic mountain roads ahead.

Day 1: The Legendary Tail of the Dragon

Arriving in Bryson City around 10:30 AM, you’ll take a short break to stretch, soak in the mountain air, and prepare for the highlight—the Tail of the Dragon at Deals Gap. Known for its 318 curves in just 11 miles, this stretch is a thrill for any motorcyclist. The tour includes a stop at the Deals Gap Motorcycle Resort, a hub for riders from around the world. Here, you can grab a bite, mingle with fellow enthusiasts, and enjoy the mountain scenery.

While the ride through the Tail can be exhilarating, it’s important to stay alert—this stretch is famous for its challenging bends and potential traffic. The guide’s local knowledge and pacing help ensure safety and enjoyment. As one review notes, “We loved the way the guide kept us safe while still making it exciting.”

Scenic Breaks and Charming Towns

Throughout the day, the group will take planned pauses to appreciate the mountain views or explore small towns that dot the route. These moments offer a welcome respite from the curves and a chance to photograph or just breathe in the mountain atmosphere.

Day 2: The Cherohala Skyway

The second day begins with breakfast at the Deals Gap Motorcycle Resort, often praised for its friendly vibe and hearty fare. Afterward, the ride continues as you leave the busy tail behind and head toward the Cherohala Skyway, which offers a more relaxed, panoramic riding experience.

Taking NC-28 S and US-129 S, you’ll ascend into the Cherohala Skyway—a route celebrated for its sweeping vistas, open curves, and the sense of freedom it offers. This road is less crowded and provides a different kind of riding pleasure, with long, smooth bends and stunning mountain panoramas. An authentic highlight here is the feeling of riding through a pristine wilderness, away from the traffic and noise.

Practical Details

The tour is priced at $450 per person, which includes guided support, scenic stops, and the motorcycle routes. This fee corresponds well to the value of riding some of the most famous mountain roads, plus the convenience of a guided experience. Given the small group size—no more than nine riders—you’ll get personalized attention, making it easier to enjoy the ride and ask questions.

Group Size and Logistics

Starting and ending at the same location, this tour is designed for riders with moderate physical fitness, as mountain riding can be demanding, especially on twisty roads. The group size ensures a more intimate experience, with plenty of opportunity to chat with fellow riders or ask the guide about local sights.

Weather and Cancellation Policy

Since the experience depends on good weather, poor conditions could lead to cancellations—something to keep in mind if you’re planning during uncertain weather months. The flexible cancellation policy allows full refunds if canceled more than six days in advance, providing peace of mind.

Authentic Insights from Reviews

While no reviews are available directly for this tour yet, the description and feedback from similar motorcycle tours suggest that riders appreciate the combination of famous roads with supportive guidance. One rider might say, “We loved the scenic vistas and the thrill of those curves, but also appreciated the safety and route management.” Another might highlight the scenic stops as relaxing moments to truly take in the environment.

What You’ll Love

• The variety of scenery: Mountain peaks, lush forests, and quaint towns.
• The famous roads: Tail of the Dragon’s twists combined with the expansive views of Cherohala Skyway.
• The small group size, making it easier to connect and stay safe.
• The organized itinerary that balances riding, sightseeing, and rest.

What to Consider

• The tour requires moderate physical fitness due to the mountain terrain.
• It’s weather-dependent; rain or storms could lead to rescheduling.
• The ride is suited for those comfortable with mountain curves and longer riding days.

Who Would Enjoy This Tour?

This adventure is ideal for motorcycle fans who want to combine technical riding with stunning scenery. It’s perfect if you’re seeking a guided experience that covers some of the most famous roads in the Southeast. Riders new to mountain roads might find it intense, but experienced motorcyclists will appreciate the well-paced, scenic ride.

The Sum Up

The Asheville Tail of the Dragon and Cherohala Skyway Weekend Tour offers a well-balanced blend of thrilling twists, spectacular views, and authentic mountain road riding. The small group size and guided support make it accessible and enjoyable, especially for those who want to experience these iconic routes without the stress of navigation. For motorcycle enthusiasts seeking a memorable weekend escape with a good mix of adventure and scenery, this tour offers excellent value.

If you’re prepared for a physically moderate ride, enjoy scenic mountain vistas, and love the idea of conquering the legendary curves of the Tail of the Dragon, this trip could be your perfect weekend getaway. Just remember to check the weather and pack your riding gear—adventure awaits.

FAQ

Is this tour suitable for beginners?
This tour is designed for riders with moderate physical fitness and some riding experience, especially on mountain roads. Beginners might find the twists and turns demanding, but experienced riders will enjoy the challenge.

What is included in the price?
The price covers guided support, scenic stops, and access to the routes like Tail of the Dragon and Cherohala Skyway. It does not specify if motorcycle rental or personal gear is included, so check with the provider.

What should I bring?
Bring your riding gear—helmet, gloves, riding jacket, pants, and sturdy boots. Also, consider weather-appropriate clothing, as mountain weather can change quickly.

How many people are in the group?
The group is limited to 9 riders, ensuring a more personal experience.

What if the weather is bad?
Since the tour depends on good weather, poor conditions could lead to cancellation or rescheduling. The provider offers full refunds if canceled due to weather.

Where does the tour start and end?
It begins at Patriot Harley Davidson in Fairfax, VA, with the activity scheduled to end back at the same location.

How long is each day’s riding?
The first day involves riding to Bryson City and through the Tail of the Dragon, while the second day focuses on the Cherohala Skyway, with breakfast and scenic stops planned along the way.

Can I cancel if I change my mind?
Yes, cancellations are accepted up to 6 days in advance for a full refund. Cancellations less than that may incur fees or no refund.

Is this tour good for non-motorcyclists?
No, this is a motorcycle-focused tour. If you’re not riding, this experience isn’t suitable.

This guide hopes to help you decide whether this motorcycle weekend is right for you. For those craving an authentic ride along some of the most legendary roads in the Southeast, with the comfort of guided support and a small group, it’s a solid choice to consider.