Guided Bike Tours

Blue Ridge Parkway

  • Date: May 18 – 25, 2024
  • Duration: 7 Days
  • Accommodation: Indoor Accomodations (Hotels/Cabins/AirBNB)
  • Support: Van Supported
  • Surface: Paved
  • Difficulty: 4.5/5 (Very Hilly)
  • Cost: $3299 (Double Occupancy), singles add $900


Explore the stunning Blue Ridge Parkway and Skyline Drive on an unforgettable Inn to Inn Bicycle Tour with WheelzUp Adventures in Cumberland, MD. Traverse scenic mountain roads, lush forests, and experience the true beauty of the Blue Ridge Mountains.

With seven days of riding covering over 332 miles, you’ll create lifelong memories. Relax in charming inns, savor local cuisine, and join us for a cycling adventure like no other. Discover the heart of the Blue Ridge with WheelzUp! 



Day 1 – (Arrival, 0 miles).

Our adventure begins in Fancy Gap, Virginia. We will gather in Roanoke and shuttle to our starting point, with a side trip to the Blue Ridge Music Center, ready to explore the Blue Ridge.

Day 2 – Fancy Gap to Floyd (43 miles)

Cycling to Floyd, we cover 43 miles. We pass the historic Mayberry Trading Post and reach Mabry Mill, a Blue Ridge icon where traditional mountain skills are on display.

Day 3 – Floyd to Vinton (49 miles)

Our ride to Vinton spans 49 miles, taking us through a rolling landscape near Roanoke. For those up for a challenge, there’s the option to tackle serious climbs for panoramic views from Roanoke Mountain or the Mill Mountain Star.

Day 4 – Vinton to Monroe (61 miles)

Departing Vinton, a six-mile climb to Great Valley Overlook kicks off the day. We continue north, taking in the stunning vistas, eventually reaching the James River, the parkway’s lowest point at 649 feet.

Day 5 – Monroe to Waynesboro (69 miles)

From Monroe to Waynesboro, we cover 69 miles, including a challenging climb to Whites Gap and a gradual descent as we approach the northern end of the Blue Ridge Parkway.


Day 6 – Waynesboro to Big Meadows (54 miles)

Cycling from Waynesboro to Big Meadows, we navigate a steep three-mile climb to the entrance of Shenandoah National Park. The route unfolds with twists and turns, offering mountain views and the beauty of Catawba rhododendron and mountain laurel.


Day 7 – Big Meadows to Front Royal (58 miles)

Our journey from Big Meadows to Front Royal spans 58 miles, featuring scenic overlooks and a thrilling 12-mile downhill ride to the Front Royal North Entrance.


Day 8 – Departure

As our adventure concludes, we enjoy a farewell breakfast and board a shuttle back to Roanoke. Our ridgeline adventure may be over, but the memories will last a lifetime.

What is Provided

Meals are included beginning with dinner the first night concluding with lunch the last day. We will dine in restaurants for breakfast and dinner. We will pack a lunch that will be available along the route.

Indoor, double occupancy, overnight accommodations are included. A limited number of single occupancy supplements are available.

For riding days, there will be fully stocked rest stops, route/mechanical support provided by experienced guides.


What’s NOT included

  • Parking fees
  • Overnight accommodations prior to the shuttle on the first day.

Appropriate Bike Type

Road or Touring Bike, 25mm tire or larger. E-Bikes are not recommended, but not restricted. 

E-Bike Requirement: Minimum 60 mile range in hilly terrain. Please contact Wheelzup.


Meet your Tour Guides

Greg Edwards

Greg Edwards, hailing from Fincastle, VA, is a passionate cyclist who embarked on his cycling journey in 1993. Over the years, he has not only explored the beauty of all 50 states in the USA on his bike but has also ventured through four countries. In 2008, Greg designed his first tour, and since then, he has organized numerous cycling tours, guiding enthusiasts through 37 states and overseas adventures. 

What truly sets Greg apart is his genuine love for helping others create enduring memories during these tours. For him, the joy of sharing the world's wonders on two wheels and creating lasting experiences for fellow cyclists is the most rewarding aspect of his adventures. Through his leadership, Greg Edwards continues to inspire and uplift the spirits of those who share in his love for cycling and exploration.

Don Annonio

Don is an avid cyclist, skier, bike mechanic, and seasoned outdoorsman. Having led bicycle tours for over 15 years, he has been a certified guide for Adventure Cycling, Empire Stateride, and many other tours.

Don has led and biked the entire Blue Ridge Parkway, and Shenandoah National Park over five times, and will be bringing his expertise and laid back approach to life along for this adventure.

Days BEFORE tour start dateCancellation Fee / Transfer Options (per person)
90 or more
  • Deposit and additional service fees are non-refundable
  • Transfers Allowed; $100 administrative fee per transfer
89 - 60
  • Total funds paid are non-refundable
  • Transfers Allowed; $100 administrative fee per transfer
59 - 30
  • Total funds paid are non-refundable
  • Transfers Allowed; administrative fee of 25% of listed tour cost per transfer
29 - Tour Start
  • Total funds paid are non-transferable and non-refundable