Asheville Tail of the Dragon and Cherohala Skyway Weekend Tour

Planning a motorcycle adventure that combines adrenaline, stunning scenery, and the chance to explore charming mountain towns? This two-day tour from Asheville, North Carolina, offers exactly that—and more. Designed for motorcycle enthusiasts looking for a structured yet exhilarating escape, this experience from Second Star Moto Tours promises 318 curves, mountain vistas, and memorable stops along the way.

What makes this tour stand out? First, the opportunity to ride some of the most famous mountain roads in the southeastern U.S. – including the Tail of the Dragon, known for its 318 curves in 11 miles, and the Cherohala Skyway, renowned for its sweeping views. Second, the combination of scenic riding with stops at quaint towns and a cozy motorcycle resort adds a touch of local flavor. Third, the manageable group size of up to nine riders means you’ll get personalized attention, plus the chance to share the ride with like-minded adventurers.

However, one thing to consider is that this tour requires moderate physical fitness—it’s all about the ride and the riding. Riders should be comfortable handling mountain curves, and the weather can impact the experience, especially in the mountains where conditions change rapidly. This tour will suit motorcycle lovers who want a well-organized, scenic weekend and don’t mind a bit of physical challenge.

In all, if you’re after an adventure-packed weekend that blends iconic roads, awe-inspiring views, and a relaxed group environment, this tour ticks many of those boxes. Perfect for those craving open-road freedom with the reassurance of guided support.

Good To Know

• Iconic Routes: Experience the famous Tail of the Dragon and Cherohala Skyway, both offering unforgettable mountain riding.
• Group Size: Limited to nine riders for personal attention and a friendly vibe.
• Duration & Price: Two days for $450 per person, making it a good value given the routes and scenery.
• Starting Point & End: Begins at Patriot Harley Davidson in Fairfax, VA, returning there after the ride.
• Physical Requirements: Moderate fitness needed—mainly handling mountain curves and riding in variable weather.
• Weather Dependence: Good weather is a must; rain or clouds may impact the experience, with options for rescheduling or refunds.

A Deep Dive into the Tour Experience

Starting Point and Logistics

The adventure kicks off at Patriot Harley Davidson in Fairfax, Virginia at 4:00 PM, providing a convenient launch for riders from the D.C. area and beyond. The tour is designed as a weekend escape, with the first day focusing on traveling from Virginia to the mountains of North Carolina, while the second day emphasizes scenic riding and memorable stops.

Day 1: From Asheville to Bryson City

You’ll depart around 9:00 AM, heading southwest along I-40 W and US-74 W. This initial stretch is mostly straightforward highway riding, gradually building anticipation for the mountain roads ahead. Arriving in Bryson City around 10:30 AM, you get a chance to stretch your legs and soak in the small-town vibe. While reviews haven’t singled out specific stops here, the town’s reputation as a gateway to the Smokies makes it a pleasant, scenic break point.

Day 2: The Roads and the Viewpoints

After a hearty breakfast at the Deals Gap Motorcycle Resort, the heart of the adventure begins. The resort is a popular hub for bikers, known for its friendly atmosphere and biker-friendly vibe. After fueling up, you’ll ride to the Cherohala Skyway, taking NC-28 S and US-129 S. This route is renowned for its sweeping curves, lush mountain scenery, and expansive vistas.

The Tail of the Dragon

The highlight for many riders is the Tail of the Dragon itself. Known globally among motorcycle and sports car enthusiasts, it’s a stretch of US Highway 129 that’s famous for its 318 curves over just 11 miles. One reviewer mentioned that the road is “more about the thrill of the curves than the scenery,” but the mountain views along the route are undeniable. Expect a lot of concentration, especially if you’re not used to such a dense concentration of curves in such a short distance.

Cherohala Skyway

Following the adrenaline rush on the Dragon, you’ll ascend onto the Cherohala Skyway. This route offers a different experience—longer sweeping turns, higher elevations, and panoramic views of mountain ranges. Riders have said that the Skyway “makes you feel like you’re on top of the world,” with vistas that stretch for miles. It’s the perfect counterbalance to the tight curves of the Dragon, offering a more relaxed but equally scenic ride.

Stops & Scenery

Throughout the ride, you’ll pass through charming small towns and mountain vistas that are best appreciated with a quick stop or photo opportunity. The tour’s structure allows for enough time to take in views and snap pictures, making it more than just a rush from point A to B.

Group Dynamics & Support

The group size maxes out at nine riders, which means you’ll get attention from your guides—important when navigating tricky curves or unfamiliar roads. The reviews praise the guides for their professionalism and friendliness. We’re told the tour is suitable for riders with moderate physical fitness, mainly because handling mountain roads requires some skill and endurance, especially if weather conditions shift unexpectedly.

Value & Cost

At $450 per person, this tour offers a lot of value—covering iconic roads, guided support, and a well-organized itinerary. For motorcyclists who value a curated experience that minimizes planning stress and maximizes riding time, this fee is reasonable. The inclusion of breakfast at the resort and the convenience of starting and ending at a central meeting point adds to the overall value.

Practical Considerations

Weather can influence the ride significantly, particularly in the mountains where rain, fog, or clouds can reduce visibility and make curves slick. The tour provider offers flexibility—if weather cancels the ride, you’ll be offered alternative dates or a full refund. Also, riders should have a moderate physical fitness level, as handling mountain roads can be demanding, especially over two days.

Who This Tour Is Best For

This adventure suits motorcyclists who enjoy a blend of scenic roads and spirited riding, especially those who like riding with a small, friendly group. It’s ideal if you’re looking for a well-organized weekend escape that combines the thrill of well-known mountain roads with the comfort of guided support. Riders with some experience handling curves and mountain roads will find this experience more enjoyable, but enthusiastic beginners with some riding skills could also get a lot from it.

If you’re after a more relaxed, sightseeing-oriented trip, this might not be your best fit. However, if the idea of tackling the Tail of the Dragon and riding the Cherohala Skyway sounds tempting—and you’re prepared for mountain weather—you’ll find this tour offers a memorable, scenic, and thrilling ride.

FAQ

How long is the tour?
The tour lasts approximately 2 days, with the main riding portion covering the iconic roads and scenic vistas.

Where does the tour start and end?
It begins at Patriot Harley Davidson in Fairfax, VA, and returns there after the ride.

What’s included in the price?
The tour fee is $450 per person, which covers guided riding, breakfast at the resort on day 2, and the scenic routes.

Is this tour suitable for beginners?
It’s designed for riders with moderate physical fitness and some experience with mountain roads. Beginners comfortable with curves and mountain riding may enjoy it, but absolute novices should approach with caution.

What if the weather is bad?
Good weather is necessary; if poor weather cancels the ride, you’ll be offered a different date or a full refund.

How many people will be in the group?
The maximum group size is nine riders, ensuring a more personal experience.

Are meals included?
Breakfast at the Deals Gap Motorcycle Resort is included on the second day; other meals are not specified but can be planned around the schedule.

Can I cancel if I change my mind?
Yes, you can cancel up to 6 days in advance for a full refund. Cancellations made less than 6 days before will not qualify for a refund, but options for rescheduling are available.

Final Thoughts

This two-day motorcycle tour offers a balanced mix of adrenaline, stunning scenery, and camaraderie. It’s perfect for riders who want to tick off one of the most famous mountain routes in the U.S., while enjoying the comfort of a guided, small-group experience. The inclusion of breakfast, the manageable group size, and the scenic routes make it a compelling choice for a weekend escape.

While weather and riding skill are considerations, those prepared for mountain conditions will find this tour rewarding. It’s particularly suited for those wanting to combine a sense of adventure with scenic beauty, all within a well-organized package that minimizes planning hassle.

If you’re craving a motorcycle weekend that combines iconic roads and mountain views with friendly guides, this tour could be your next great ride. Just pack your gear, bring your sense of adventure, and get ready to carve through some of the best curves the Southeastern U.S. has to offer.