Shenandoah National Park Weekend Cycling

Trip Length 4 Days
Group Size 4-11
Activity level
Starting from
$1,999 for REI Members
$2,194 for non-members
Departures Jun 2020-Oct 2020

Spend 4 days of challenging and rewarding cycling through the Shenandoah Valley, along Shenandoah National Park?s famed Skyline Drive, while staying in charming inns and lodges.

Carved by the Shenandoah River, and nestled between the Blue Ridge Mountains and the Appalachians, the Shenandoah Valley is one of Virginia's most picturesque regions. Its natural beauty and short distance from the nation?s capital make it an ideal destination for cyclists looking for a rewarding weekend adventure. Known for its importance as the breadbasket of the Confederacy during the Civil War, the valley saw many battles during that period. Dotted with small, rural and occasionally forgotten communities, the valley is also home to many quaint, historic inns, which provide cozy and relaxing nights after our long days in the saddle.

Created in 1925, Shenandoah National Park was one of the first National Parks designated in the eastern United States. For cyclists, the centerpiece of the park is the 105-mile Skyline Drive, stretching from Front Royal to Waynesboro along the spine of the Blue Ridge Mountains. The roadbed was not built by the Civilian Conservation Corp, but it did build the many guard rails and walls, and graded the slopes on either side of the road. The CCC also built overlooks, campgrounds and picnic areas, in addition to planting trees and shrubbery alongside what would become Skyline Drive. With more than 75 overlooks with awe-inspiring views of the Shenandoah Valley and the farmlands of eastern Virginia, Skyline Drive is the very definition of a Scenic Byway. A particular point of interest is Mary's Rock Tunnel, a 670-foot bore through solid granite that was completed in 1932.

This tour offers breathtaking views, abundant natural beauty and Civil War history, along with some of the most thigh-burning climbs and exhilarating descents you?ll find anywhere in the Eastern US. And we do it all in a 4-day spin, staying at inns and lodges each night with full professional support throughout.

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Trip Highlights

  • Ride all 105 scenic miles of Shenandoah National Park's Skyline Drive
  • View the Blue Ridge Mountains from the valley floor to the top of Skyline Drive
  • Witness the blossoming of spring and the vibrant colors of fall?both spectacular in Virginia
  • Embrace the long, burning ascents and exhilarating descents along calm, curvy, tree-lined roads
  • Take in breathtaking views from Bearfence Mountain summit, Stony Man, The Point, Thorofare Mountain, Buck Hollow and Range View Overlooks


This trip is rated Vigorous [4]. Participants should have cycling experience and be comfortable in the saddle for 5-7 hours per day. Rides consist of both moderate and more vigorous cycling days covering 40-60 miles in distance and total daily elevation gain between 3,000'-6,700'. Vehicle support will be available throughout the trip when needed.

We recommend a conditioning program beginning at least 3 months prior to departure that incorporates rides of at least 40-60 miles. The better cycling shape you're in, the more you'll enjoy all this trip has to offer!

  • Cycling
  • Road Cycling

What's Included

Lodging and meals as indicated on the daily itinerary. Professional guide services. Transportation during the course of the trip. Flat or drop bar road bike, e-bike (guest's choice).


Hotel or lodge, 3 nights.

Your wheels for the journey

Every great tour begins with a great bike, and our top-flight fleet has been carefully curated for your cycling adventure.

Want to bring your own bike?  You can do that too.

Your Adventure Itinerary

Day 1

Front Royal and the Shenandoah Valley

We meet our guides at the REI store in Fairfax, VA at 10am, picking up any last-minute gear you may need for the ride. After loading up the bikes we hop in the van and head to Front Royal, where we begin our 200-mile loop down the Shenandoah Valley and back north along Skyline Drive in Shenandoah National Park. After a box lunch, we get our bike fit dialed in and mount up for a warmup ride to Luray, VA. This route covers low-traffic, rural, scenic roads shaded by the Blue Ridge Mountains to the east, with the Shenandoah Valley and the Appalachian Mountains to the west. We cycle the lower foothills of the Blue Ridge range, so the route will be anything but flat?a perfect primer for the hilly days ahead. After our 40-mile ride, we reach Luray, VA and our accommodations for the night. Hot showers, a hearty meal, and comfy beds warmly welcome us. We watch the sunset over the Appalachians before settling in for the evening. Lunch and dinner included.

Cycling: 40 miles (3-5 hours, paved road), Elevation gain/loss: +3,021? / -2,722'; Van transfer: 1 hour

Day 2

Cycle the picturesque valley from Luray to Waynesboro

After a hearty breakfast and our daily route review, we roll out for a wonderful day of cycling? more miles, more hills, but even more smiles. We ride south through the Shenandoah Valley, making our way to Waynesboro, the southern terminus of Skyline Drive and the northern terminus of the Blue Ridge Parkway. As the sun lights up the valley from the east, we ride through the rural Virginia communities that line the foothills of the Blue Ridge range, on low-traffic roads hugging the valley?s eastern slopes. We have lunch at a well-known local eatery around midday before finishing our ride with a series of inclines pointing us to Waynesboro, where the mountain slopes we?ll ride tomorrow awaits. Another filling meal, beautiful sunset and perhaps an adult beverage top off this invigorating day. All meals included.

Cycling: 59 miles (5-6 hours, paved road), Elevation gain/loss: +3,555? / -2,749'

Day 3

A ride on postcard-perfect Skyline Drive to Big Meadows Lodge

This is the day we?ve waited for! After a very early, hearty breakfast, we begin the slow, steady climb to the entrance of Shenandoah National Park. The 6,000? of climbing on our first two days gets eclipsed today, when we cover 6,700? of elevation over 60+ miles. It?s all uphill to the park entrance, with no relief from the ever-increasing grade. Once we reach Skyline Drive, we turn north and continue the climb to our first overlook. Our guides are with us all the way, providing support for every rider?s needs throughout the day. Uncountable spectacular vistas along the roadway provide ample opportunity to rest while absorbing the natural beauty of the region. The phrase "for every uphill there is a downhill" comes to life as we ride up one long grade, then cruise down another, then do it all over again. We?re rewarded midday with a guide-prepared lunch at one of the many scenic overlooks. Our relaxing accommodations and a hearty dinner at Big Meadows Lodge help cap the night off. All meals included.

Cycling: 61 miles (6-7 hours, paved road), Elevation gain/loss: +6,672? / -4,592'

Day 4

Descend into Front Royal and return to Fairfax

On our final day, we depart Big Meadows Lodge after breakfast and continue along the Skyline Drive for the last 50 miles of our journey. The 4,000? of climbing is rewarded with nearly 6,400? of exhilarating descents. The parkway continues to meandering in and out of the many small gorges, gaps and divides within the park. Deer, black bear, wild turkey and a host of other wildlife regularly cross Skyline Drive, so we should catch a glimpse of some critters throughout the day. A big highlight today is Mary?s Rock Tunnel, a 670? bore through the solid granite of Mary's Rock. Our guides provide lights for the ride through the tunnel. Our cycling adventure ends with a bang?a 10-mile, 2,000? descent to the Shenandoah Valley Overlook. Here we take in one last view of the majestic Shenandoah Valley while our guides load up our bikes. We hop in the van for a short ride to our celebratory lunch, then make our way from Front Royal back to Fairfax, where we bid each other happy trails. All departing flights should be scheduled for after 7:30pm this evening. Breakfast and lunch included.

Cycling: 50 miles (3-4 hours, paved road), Elevation gain/loss: +4,085 ? / -6,337'; Van transfer: 1.5 hours

Gear List

This gear list has been created to help you choose the best equipment for the trip. Try to bring only what is necessary, as this will help you and the field staff. The weather and other conditions at the time of your arrival will dictate what clothing and equipment you will be required to use each day and what (if anything) can be left behind. It may be a necessary precaution that you bring certain items on the list, even if it is uncertain whether or not they will be needed.

Collection of selected R E I Co-op cycling merchandise and snacks laid out to pack for a bike tour

What to pack

Contact Us

Feel free to give us a call at 800-622-2236 should you have any questions regarding the gear list. The staff at our stores and Direct Sales (800-426-4840) will also be happy to help you with gear questions. Or check out REI Expert Advice , which has great information to help you prepare for your trip.