Bike Tours

WheelzUp Adventures offers a variety of guided and self-guided bike tours that include bike rentals, helmets/gear, and shuttle services. Some weeklong tours include overnight accommodations. Whether you’re a solo explorer or traveling with friends, our tours offer a range of options to suit your preference.

Blue Ridge Parkway

7 Day Guided Bike Tour (May 18 – 25, 2024)

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!

Trans Virginia Backcountry Gravel

7 Day Guided Bike Tour (May 11th – 17th, 2024)

Explore Virginia’s backcountry on a gravel bike tour with Wheelzup Adventures in Cumberland, MD. The TransVirginia Route offers a diverse and challenging cycling experience.

You’ll start alongside mountain streams with rhododendron-lined paths, then head up to Wind Rock Overlook at Mountain Lake, known for its role in Dirty Dancing. Afterward, enjoy a leisurely ride on the historic New River Trail, and take in the wonderful gravel riding in the Mount Rogers Recreation Area.

One more mountain climb leads to the Virginia Creeper Trail, a must-visit for gravel cyclists and a Rail Trail Hall of Fame inductee.

 Join Wheelzup Adventures for this unique journey through Virginia’s backcountry, where you’ll encounter diverse landscapes and communities. It’s a memorable gravel biking adventure that combines challenge, history, and natural beauty.

Road Riding with a Guide

Explore some of the beautiful empty mountain roads of Western Maryland, Pennsylvania and West Virginia on a bicycle, but let us do all the planning.

Everyday of the week, however, requests have to be approved by the store. Customers can make requests and payment holds, the shop will need to approve or decline requests.

Interested in road riding, but don’t want to have to deal with route finding, navigation, finding all the cool points of interest? Let one of our guides take you on the wonderful windy, quiet roads of western Maryland. Let us know the duration, difficulty and type of riding you would like to do and we will take you on one. We offer everything from simple rolling road routes, mixed surface, big climbs and extended gravel routes. We also have top of the line bikes which make the experience much more enjoyable.

The Big Deal Ride

 25 miles on the Great Allegheny Passage Trail (All Downhill)

The Big Deal ride is our most popular ride. It includes bike rentals, a helmet and a shuttle to the trailhead at Deal, PA, next to the Eastern Continental Divide. From there, it is a 25 mile ride back to Cumberland. Experience some of the best parts of the trail, highlights include the big savage tunnel, The big savage overlook, the Mason Dixon line, Helmstetter's Curve and the Bone cave. Did we mention the best part, it’s all downhill – perfect for all members of the family.

Rocky Gap Mountain Bike Ride

Mountain Biking at Rocky Gap State Park

Ride the lakeside loop with great rocky and intermediate-level trails. Which circumnavigates Lake Habeeb. Let a few guides ride with you and show you the local stash that meets the level of challenge you are looking for. Finish the day with a dip in the lake, some time at the Casino or go fishing on the lake (MD fishing license required).

gap trail bike tour

GAP Trail and C&O Canal Self Guided Tours

Choose your own adventure

We provide logistical support for self-guided bike tours for the GAP Trail, C&O Canal and the surrounding region. Sit back, relax, and let us take care of your transportation needs, so you can fully immerse yourself in the breathtaking landscapes and unforgettable experiences that await you on these incredible bike trails. Our GAP Trail & C&O Canal shuttle services and bike rentals cater to all experience levels, ensuring you have a comfortable and enjoyable trip.