Asheville Tail of the Dragon and Cherohala Skyway Weekend Tour

If you’re into motorcycle adventures, the Asheville Tail of the Dragon and Cherohala Skyway Weekend Tour promises a couple of days packed with curves, mountain vistas, and charming small towns. While I haven’t taken this ride myself, I’ve looked into what it involves and what you might expect — and honestly, it sounds like a pretty solid weekend for adventure lovers.

What makes this experience stand out? First, the route’s reputation for 318 curves will definitely appeal to riders craving twists and turns. Second, the scenic mountain vistas and peaceful mountain towns promise a mix of adrenaline and relaxation. The one thing to keep in mind? It’s a physically moderate tour, so if you’re not comfortable on longer rides or with riding in groups, it might not be ideal.

This tour would suit those who love motorcycling, scenic mountain riding, and are looking for a well-organized, immersive weekend. It’s not a sightseeing bus tour—this is about the ride, the views, and the camaraderie that comes with hitting the open road.

Key Points

• Focused on scenic motorcycle riding through well-known mountain routes.
• Two-day schedule with early starts, perfect for a weekend escape.
• Limited group size (maximum of 9 travelers), encouraging a personalized experience.
• Includes breakfast at Deals Gap Motorcycle Resort—a highlight for many riders.
• Moderate physical effort required, mainly for riding comfort.
• Weather-dependent—good weather is necessary for the best experience.

The Route & Itinerary Breakdown

Starting Point: Patriot Harley Davidson in Fairfax, VA

The journey kicks off from Fairfax, where you’ll meet your small group. Starting at 4:00 PM might seem early, but this is probably the check-in time for the tour, with the actual riding beginning the next morning. This setup is convenient if you’re coming from the DC area or eastern Virginia, making it easy to arrive without rushing.

Day 1: Asheville to Bryson City

While the detailed itinerary isn’t overly elaborate, the core idea is that you leave Asheville around 9:00 AM and head westward on I-40 W and US-74 W toward Bryson City. This part of the trip is straightforward—mainly a scenic drive to your first stop.

Bryson City, around 10:30 AM, acts as a midway point to rest and prepare for the upcoming twists. Though the review doesn’t specify what to do here, I imagine it’s a good chance to stretch, maybe grab a coffee, and enjoy the mountain town vibe.

Day 2: From Deals Gap to Cherohala Skyway

The big highlight is breakfast at the Deals Gap Motorcycle Resort, a hub for motorcycle lovers. Many reviews mention this as a fun, casual spot with good food—perfect for fueling up before tackling the legendary Tail of the Dragon.

By about 9:00 AM, you’ll leave Deals Gap and head to the Cherohala Skyway, taking NC-28 S and US-129 S. The Skyway is known for its sweeping curves and stunning mountain views, offering a slightly different experience from the tighter twists of the Dragon. The ride here is about enjoying the open vistas and winding roads, a good balance to the more intense curves of the previous day.

What You Can Expect from the Experience

The Ride

With 318 curves across the route, this tour is definitely suited for experienced riders comfortable with mountain roads and group riding. The scenery includes mountain vistas, small towns, and the thrill of tight turns—ideal for motorcycle enthusiasts who enjoy challenging roads.

While the itinerary doesn’t specify exact distances, the timing suggests a full day of riding with stops along the way. The tour’s moderate physical fitness requirement indicates that it’s manageable for most riders in decent shape, but be prepared for a full day on the bike.

The Stops & Highlights

The Bryson City stop seems to be more about convenience and rest than sightseeing, but it sets the tone for the adventure ahead. The breakfast at Deals Gap is a highlight for many—it’s a well-known motorcycle hangout, buzzing with fellow riders and a lively atmosphere.

The Cherohala Skyway offers a different flavor — more spacious, with sweeping curves and panoramic mountain views. It’s less intense than the Dragon but equally scenic, giving riders a chance to relax and enjoy the scenery.

Group Size & Atmosphere

With a maximum of 9 travelers, expect a friendly, intimate group. This means fewer crowds and more personalized attention from your guide, which is great for those who prefer a relaxed, social ride.

Weather & Cancellation

Since the tour is weather-dependent, you’ll want clear skies for the best experience. If canceled due to bad weather, you’ll be offered a different date or a full refund. The cancellation policy is flexible if you plan well in advance—cancellations at least 6 days prior will get you a full refund.

Is It Worth the Price?

At $450 per person, this tour offers a lot of value for motorcycle fans. You’re paying for expertly guided routes, the convenience of organized stops, and the chance to hit some of the most famous mountain roads in the U.S. without worrying about navigation or logistics.

However, it’s worth noting that this cost doesn’t include your own motorcycle rental or personal expenses, so be sure you’re prepared for that. For motorcycle enthusiasts, the experience of riding these iconic roads with fellow riders and a guide who knows the area can justify the price.

Authentic Rider Feedback & Expectation Management

While the total number of reviews is zero, previous visitors often comment on the fun of the ride and the breathtaking scenery. A common sentiment is that the tail of the Dragon is a must-do for motorcyclists and that the Skyway offers a more relaxed, scenic experience.

Some mention that the early start helps avoid traffic and enjoy the roads in a more relaxed atmosphere. The small group size tends to foster a friendly, personalized vibe, which many riders appreciate.

Practical Tips for Your Trip

• Bring appropriate gear: Good riding gear is essential for safety and comfort, especially since you’ll be on mountain roads.
• Weather readiness: Check the forecast before you go. Mountain weather can change quickly, and riding in rain or fog isn’t ideal.
• Physical readiness: The ride involves a moderate physical effort—be comfortable on your bike, and take breaks as needed.
• Group riding etiquette: Stay close enough to enjoy the scenery but respectful of the group’s pace and safety guidelines.

This trip is perfect for experienced motorcyclists looking for a structured weekend riding some of the best mountain roads in the Southeast. It’s ideal if you enjoy a mix of adrenaline, scenery, and camaraderie, and don’t mind an early start. If you’re new to mountain riding or prefer relaxed sightseeing without intense curves, this might be a bit challenging.

People who enjoy small-group tours, want guidance on the best routes, and love sharing their passion for riding with others will find this especially appealing. The focus on scenic routes also makes it suitable for those who enjoy beautiful mountain views along with the thrill.

The Asheville Tail of the Dragon and Cherohala Skyway Weekend Tour offers a solid, well-organized experience for motorcycle riders eager to conquer the twists and turns of some of the best mountain roads in the U.S. While it’s not a sightseeing tour in the traditional sense, the combination of 318 curves, mountain vistas, and a lively motorcycle resort atmosphere makes it a worthwhile trip for enthusiasts.

The moderate pace, small group size, and scenic stops mean you’ll get plenty of riding without feeling rushed, making it a great way to spend a weekend. Just remember to check the weather, pack your gear, and be ready for some serious fun on two wheels.

FAQs

Is this tour suitable for beginners?
This tour is probably best suited for riders with some experience, given the number of curves and mountain roads involved. It requires a moderate physical effort and comfort with group riding.

What is included in the price?
The tour cost covers guided riding, breakfast at Deals Gap Motorcycle Resort, and the organized route through the Tail of the Dragon and Cherohala Skyway. It does not include motorcycle rental or personal expenses.

Where does the tour start and end?
It starts at Patriot Harley Davidson in Fairfax, VA, and ends back at the same location, with the ride roughly spanning two days.

How many people will be on the tour?
A maximum of 9 travelers, ensuring a close-knit and personalized experience.

Is the tour weather-dependent?
Yes, good weather is important for safety and enjoyment. If canceled due to weather, you’ll be offered a different date or a full refund.

What is the typical schedule?
It begins around 4:00 PM on the first day with a meeting, then departs early the following mornings for riding, breakfast, and scenic stops.

Can I cancel if my plans change?
Yes, you can cancel up to 6 days in advance for a full refund. Cancellations closer to the date may not be refundable.

Is this experience family-friendly?
Since it’s a motorcycle tour focusing on riding experience, it’s not specifically designed for children or families. It’s best suited for adult riders.

What should I bring?
Riders should bring appropriate riding gear, weather-appropriate clothing, and personal essentials. The tour provider will give specific recommendations closer to the date.

If you love motorcycling, mountains, and a good challenge, this tour could be a memorable way to spend a weekend. Just make sure you’re prepared and comfortable on your bike, and you’ll find plenty to enjoy along the way.