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Northern Shenandoah Bicycle Tour 
A bicycling vacation of the northern Shenandoah Valley, Massanutten Mountain and Skyline Drive 

Apple orchards, equestrian estates, and the numerous overlooks of Skyline Drive provide the setting for this tour for bicycling enthusiasts. Several great climbs punctuate our tour through the countryside of northern Virginia. We'll tackle Massanutten Mountain, a long ridge that bisects the Shenandoah Valley, and Skyline Drive, one of America's most beautiful national parks. We will enjoy a different inn each night, each with a very different personality.

Cyclists at a Skyline Drive Overlook

Day 1 l Day 2 l Day 3 l Day 4 l Day 5 l Day 6 l Lodging l Getting There l Cycling  

(***Note: We are still offering our fabulous Southern Shenandoah Tour beginning in Staunton, VA and including portions of the Blue Ridge Parkway. Click here for additional details on that tour destination.)

Northern Shenandoah Tour Fast Facts:
Highlights: Dates: Price:

Spectacular road cycling including all of the 
famous Skyline Drive

Pastoral back roads of the Shenandoah Valley

Charming Winchester, VA

Gourmet dinners

6 days / 5 nights

2018 Dates T.B.A. Soon.
Opt in for email date
announcements here:


2018 Tour Price:
T.B.A. / person
Price range reflects early to late enrollment.  

Bike rental: $100

Single occupancy room supplement: $450

Tour prices subject to change

Dates with an asterisk * have a solo traveler hoping for a roommate--  Call for details
RESERVE YOUR SPOT (click here)  


Day 1: 

Meet in Charlottesville, VA ready to bike. Arrive a day earlier if you'd like to explore this vibrant university town. We pedal from town today into the Blue Ridge Mountains that loom just to the west. The route will pass beautiful farms in the valley before tackling a challenging climb up to the Blue Ridge Parkway. A spectacular descent takes us into Waynesboro, where we spend the night at the lovely and spacious Iris Inn.  Our innkeepers will provide a delicious dinner as well.

Bicycling Route, Inn to Inn:  42 miles, 3585 feet of climbing

Day 2: 

Rise early for breakfast, then climb back up to the southern terminus of Skyline Drive (or opt to start the day with a shuttle.) From there we will bike north on Skyline Drive, a scenic driving route contained within Shenandoah National Park. Offering frequent scenic overlooks and a speed limit of 35 mph, this route is ideal for road cyclists. Today we will be exiting Skyline Drive with a descent back into Shenandoah Valley. Back roads will take us to our destination for the evening -- downtown Luray. Our inn offers a pool for relaxing.  We dine together in the elegant dining room onsite.

Bicycling Route, Inn to Inn:  79 miles, 4505 feet of climbing

Day 3: 

Biking away from Luray, we make our way to the looming ridge of Massanutten Mountain. A steep climb up the side of the mountain ridge rewards you at the top with sweeping vistas of the northern Shenandoah Valley. We will bike quiet roads north on our way to Strasburg. From there, we enter apple country, with lovely orchards on both sides as we make our way to Winchester, VA. The night's lodging is in Old Town, convenient to the vibrant pedestrian mall.  We'll dine together at a fine nearby establishment.

Bicycling Route, Inn to Inn:  61 miles, 2185 feet of climbing

Bicycling down a hidden Virginia valleyDay 4: 

You may just be ready for a day off the bike today. So, slow down and relax. For 2009, we have added a second night in Winchester so that you may do just that. You can take your time strolling the pedestrian mall, visiting museums, or just relaxing in your beautiful room at the George Washington Hotel. Of course, we are going to offer an optional but fully supported bike ride as well. We'll guide the willing through the rolling farmland outside of town for a 30 - 50 mile ride.  Dinner tonight is "on-your-own" in historic Winchester.

Bicycling Route, Inn to Inn:  41 miles, 728 feet of climbing

Day 5: 

Departing Winchester to the east, we will make our way past beautiful equestrian estates and quiet valley roads as we approach the town of Front Royal to the south. Front Royal is the northern entrance Skyline Drive. Fifty miles of climbing, descending and panoramic overlooks entertain us on our journey to historic Big Meadows Lodge. Skyline Drive is a result of the vision of President Herbert Hoover in the late 1920's, and was built as a W.P.A. project in the 1930's. It is purely for recreational use, both as a scenic drive, and as the means of access to hiking trails and campgrounds throughout Shenandoah National Park.  Dinner is as a group in the historic main lodge building.

Bicycling Route, Inn to Inn:  72 miles, 5774 feet of climbing

Day 6: 

We complete our Skyline Drive experience today by continuing southward. We'll exit to the east, returning to the rolling farmland north of Charlottesville. We bike back to the Hampton Inn, where showers and a final catered lunch will be available prior to departure.

Bicycling Route, Inn to Inn:  60 miles, 1729 feet of climbing, 4846 feet descending



Optional Nights before or after tour:  Hampton Inn & Suites, Charlottesville at the University, Charlottesville, VA.  We will meet and return to this inn.  With all of the conveniences of a typical Hampton Inn, this one is located in a vibrant neighborhood that is walking distance to both the historic downtown pedestrian mall and the UVA campus.

Night 1:  Iris Inn, Waynesboro, VA.  Dave and Heidi Lanford welcome you to this modern facility nestled on 11 wooded acres, on the west side of the Blue Ridge Mountains.  Rooms are spacious and graciously appointed.  There is plenty of room to spread out on the covered porches, back deck, and great room.

Night 2:  Mimslyn Inn, Luray, Virginia.  A multi-million dollar restoration has brought back the elegance of this 1931 hotel in the heart of beautiful Luray.  Each of the 45 rooms has been individually decorated with relaxing color schemes, beautiful fabrics, rich patterns, classic furnishings and modern amenities. Large windows with natural light illuminate most rooms, allowing the vivid landscape of the outdoors to be seen.
Nights 3 & 4:  The George Washington Hotel, Winchester, VA.  This historic hotel is located a short walk from everything in historic downtown Winchester, Virginia, at the north end of the Shenandoah Valley.  Newly renovated by the Wyndham corporation, it will offer the charm, grace and sophistication of the past while featuring modern amenities for the 21st century. Superior accommodations are paired with the finest service.

Night 5:  Big Meadows Lodge, Skyline Drive, VA.  Located at 3,500 feet above sea level Big Meadows offers perfect views of the picturesque surroundings that have drawn visitors to Shenandoah National Park for generations.


All meals are included, with the exception of one "on-your-own" night in Winchester.  This includes substantial breakfasts, picnic lunches, gourmet dinners and abundant snacks and beverages.


This tour is a roadie's dream, and is appropriate for intermediate or advanced bicyclists.  We recommend modern road bikes, preferably with triple chainrings or large rear cogs to tame the hills.  All biking is on asphalt roads except for a few very short sections of packed gravel.  Distance options each day range from 50 to 80 miles, with optional side routes available to add on miles, and designated shuttle opportunities to shorten miles and cut out the biggest climbs.  Terrain is a mix of rolling hills and strenuous climbs.  The scenery is very beautiful and diverse, including valley farms, forested mountains, and Skyline Drive.


Getting to the Tour Start (Charlottesville, VA):

Charlottesville Albemarle Airport is just north of town.  
US Airways Express, United Express, Northwest Airlines, and Delta Connection provide non-stop service to six major connecting cities.

Ground Transportation:  Several car rental agencies are available at the airport.  Hampton Inn and Suites at the University offers a complementary ground shuttle from 7 a.m. to 11 p.m.  

Driving:  Charlottesville is located I-64.  It is 62 miles from Richmond, VA, 116 miles from Washington, DC, 241 miles from Raleigh, NC, and 544 miles from Atlanta, GA.

Timing:  We bike away from Charlottesville on the first morning of the tour.  Try to arrive there no later than 9 a.m., 8:45 a.m. if you are renting a bike from us.  Departure time from Charlottesville on the last day will be around 3 p.m.

Carolina Tailwinds guides tours in Shenandoah National Park/Skyline Drive under a Commercial Use Authorization issued by the park.

Carolina Tailwinds reserves the right to make alterations to the itinerary as needed.  Any changes made will maintain or enhance the quality of the tour.  Prices are subject to change.


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