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Shenandoah Valley Gravel Bike Tour

Discover an unpaved cycling paradise surrounding Harrisonburg, Virginia

On our Shenandoah Valley Gravel bike tour, you'll discover the beauty of Virginia's breathtaking landscapes and uncharted roads. It is a region known for its undulating terrain, historic towns, and farmlands that reach to the horizon. Journey along pristine unpaved roads nestled in the broad valley between the Blue Ridge and Allegheny Mountains. Wind your way through quaint Mennonite communities on the outskirts of historic Harrisonburg. Pedal beneath canopies of black walnut trees and towering oaks and admire sweeping views as you pass through centuries-old towns and communities that retain much of their original character. Enjoy an epic gravel adventure through the forest to the summit of Reddish Knob and enjoy the views. Refuel each day with meals from small cafes and welcoming restaurants serving up delicious fare. If you have been searching for friendly people, small-town vibes, a local food ethos, and an outstanding hub for outdoor recreation, look no further — your gravel adventure in Virginia’s Shenandoah Valley awaits. Book your trip with confidence »
Learn if a Gravel trip is right for you »
Shenandoah Valley Gravel Bike Tour
$1899 Per Person
5 Days & 4 Nights
Rider Level: ?
3 - Active Non-riders Welcome
Trip Style: ?
Hotel Level: ?
From $1899 per person View All Details
Trip Wows
Explore the Shenandoah Valley's endless array of undulating roads with breathtaking views at every turn
Unwind at one hotel, an easy walk away from vibrant downtown Harrisonburg
Tackle the iconic climb to Reddish Knob and be rewarded with panoramic views
Savor wood fired pizzas at Bella Luna and tasty farm-to-table fare at Rocktown Kitchen
Enjoy rides through peaceful, verdant farmland deeply rooted in the Brethren and Mennonite traditions that have shaped the surrounding communities
Shenandoah Valley Gravel Bike Tour
I loved the whole flow of the trip, and the way each day built off the previous day. I especially appreciated the mixture of pavement and gravel, the rolling hills, and the day of a long, more serious climb. Each day's trip was also well thought out with perfect rest stops in great locations for shedding clothing or getting refueled. I loved the bike, the shifting was terrific, and I especially loved the grippy tires.
-Brenda, Trek Travel Guest

Dates & Prices

The Earlier You Book, The Greater The Rewards

We reward our guests with lower pricing and more dates to choose from the earlier you book. Rest assured, once you book, your price is guaranteed.
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Single Occupancy from: +$399
Apr 8 – Apr 12 
Guaranteed Limited Availability
$1999 / Person, Double Occupancy / Plus 5.3% state and local sales tax / Discover trip inclusions Book this date
Apr 22 – Apr 26 
$1899 / Person, Double Occupancy / Plus 5.3% state and local sales tax / Discover trip inclusions Book this date
May 13 – May 17 
Guaranteed Limited Availability
$2099 / Person, Double Occupancy / Plus 5.3% state and local sales tax / Discover trip inclusions Book this date
Jun 3 – Jun 7 
Guaranteed Limited Availability
$1999 / Person, Double Occupancy / Plus 5.3% state and local sales tax / Discover trip inclusions Book this date
Aug 26 – Aug 30 
$1899 / Person, Double Occupancy / Plus 5.3% state and local sales tax / Discover trip inclusions Book this date
Sep 2 – Sep 6 
$1899 / Person, Double Occupancy / Plus 5.3% state and local sales tax / Discover trip inclusions Book this date
Sep 9 – Sep 13 
$1899 / Person, Double Occupancy / Plus 5.3% state and local sales tax / Discover trip inclusions Book this date
Sep 16 – Sep 20 
$1899 / Person, Double Occupancy / Plus 5.3% state and local sales tax / Discover trip inclusions Book this date
Sep 23 – Sep 27 
$1899 / Person, Double Occupancy / Plus 5.3% state and local sales tax / Discover trip inclusions Book this date
Sep 30 – Oct 4 
$1899 / Person, Double Occupancy / Plus 5.3% state and local sales tax / Discover trip inclusions Book this date
Oct 7 – Oct 11 
$1899 / Person, Double Occupancy / Plus 5.3% state and local sales tax / Discover trip inclusions Book this date
Oct 14 – Oct 18 
$1999 / Person, Double Occupancy / Plus 5.3% state and local sales tax / Discover trip inclusions Book this date
Don't see your ideal travel date? 
Call us at (866) 464-8735 for custom date availability
Looking for a one of a kind, once in a lifetime experience?
Look no further. Choose your trip date, get your group together and we will do the rest. Private trip pricing is as follows:

  • 10+ Guests Price as advertised*
  • 8-9 Guests +$750 per person to trip price*
  • 6-7 Guests +$1,500 per person to trip price*
  • 4-5 Guests +$2,000 per person to trip price*
  • 2-3 Guests +$3,000 per person to trip price*
  • 1 Guest        Call us for pricing*

Traveling with a small group? Consider semi-private trips.
For groups of up to six people, semi-private trips offer unique flexibility within a larger Trek Travel guided trip. Learn more »

*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Private pricing is not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Looking for a date that you don’t see?
Look no further. Simply tell us your preferred travel dates and we’ll work together to deliver the same great trip on your custom schedule.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom dates are not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Want to customize this trip?
We've got you covered. We’ll work with you to build your perfect vacation from scratch, including your choice of riding, accommodations and dining options. With the help of our trip designers and travel experts, the world is available like never before.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom trips are not available on Ride Camp, Race, Special Edition or Cross Country style trips.

YYour Trek Travel guides will meet you at Hotel Madison at 11:00 AM on the first day of the trip. After a 30-minute private shuttle, you’ll arrive in the small community of Briery Branch. Enjoy a picnic lunch prepared by your guides and get to know your fellow travelers. After a short round of introductions, your guides will discuss the rules of bike safety and specific cycling tips for riding in the Shenandoah Valley before familiarizing you with your Trek Checkpoint gravel bike and ensuring a comfortable fit. Afterward you will set out on your first ride of the week, which traverses the farmland west of Harrisonburg. Long range views and well-kept farms abound as you get your first taste of the gravel roads of the Shenandoah Valley. Once back at Hotel Madison, take some time to settle into your room and grab a drink at the hotel bar on Trek Travel. This evening you will walk a short distance into downtown Harrisonburg with the group to enjoy a delicious dinner of Italian-inspired dishes and wood-fired pizza at Bella Luna.

Today's Ride:

Briery Branch to Harrisonburg
Approximately 21 mi | 34 km and 1,250 ft | 381 m


Hotel Madison

Included Meals:

Lunch | Dinner

Following breakfast, you'll board a private shuttle for a 40-minute transfer to a coffee shop in Staunton, known as the Queen City of the Shenandoah Valley. Here you will begin a challenging and fantastically scenic loop ride through the farms and forests south of town. The road turns from pavement to gravel and back again numerous times throughout today's routes. Take in views of historic mills, beautiful barns, and cattle and sheep farms as you make your way around the loop of your choice. Afterwards, a fresh lunch awaits at Bryer Street Bistro in downtown Staunton. Take some time to wander the historic streets of this centuries-old town before boarding the shuttle back to Harrisonburg. This evening you are on your own for dinner, with Harrisonburg's array of restaurants a short walk away.

Today's Ride:

Staunton Loop
Approximately 47 mi | 76 km and 3,200 ft | 975 m

Short Option:

Staunton Loop with McKinley Road Cutoff
Approximately 41 mi | 66 km and 2,700 ft | 823 m

Avid Option:

Staunton Loop with Newport Road
Approximately 50 mi | 80 km and 3,400 ft | 1,036 m


Hotel Madison

Included Meals:

Breakfast | Lunch

After fueling up for the day you'll ride from Hotel Madison to explore the roads that lie to the northwest of Harrisonburg. As with the first two days, you can expect a lot of twists and turns and consistently hilly terrain. You'll ride through historic downtown and neighborhood roads before transitioning into the pastoral countryside that defines so much of the Shenandoah Valley. With three loop options to choose from, you decide how many miles you want to pedal before returning to town for lunch of your choice. This afternoon is your opportunity to walk around downtown and visit the shops and restaurants of Harrisonburg. The campus of James Madison University is adjacent to our hotel and also makes for a beautiful walk. Your guides will offer their suggestions for how to make the most of your time this afternoon as well as a list of the best restaurants and breweries to visit this evening.

Today's Ride:

Singer's Glen Loop with Tide Springs Road
Approximately 33 mi | 53 km and 2,350 ft | 716 m

Short Option:

Singer's Glen Loop
Approximately 24 mi | 39 km and 1,550 ft | 472 m

Avid Option:

Turleytown Loop
Approximately 47 mi | 76 km and 2,050 ft | 625 m


Hotel Madison

Included Meals:


Following breakfast, you'll shuttle 30 minutes to Stokesville for what promises to be the most memorable ride of the week! You'll have two options - one paved and one gravel - to reach the summit of the iconic Reddish Knob. At 4,398 feet, Reddish Knob stands above most other peaks in Virginia and the eastern Allegheny Mountains, offering stunning panoramic views at the top. Today's ride ventures north on gravel, before turning onto Briery Branch Road to begin a paved 9-mile climb, with an average grade of 5.8%. The avid option heads out in the opposite direction for a punchy paved warm-up followed by a true gravel adventure. You'll climb over 14 miles of gravel on forest service roads including various sections of loose, chunky dirt and rock that will challenge and delight experienced gravel riders. The support van will follow today's ride, while the avid option will be supported by a ride guide. Both routes meet at the summit, where you'll have a chance to celebrate and savor the views before enjoying the long, flowing paved descent. Back in Stokesville, a well-earned picnic style lunch awaits. Revel in this beautiful and challenging day as you shuttle back to Harrisonburg and prepare for your final night's farm-to-table dinner at the bustling Rocktown Kitchen.

Today's Ride:

Stokesville to Reddish Knob & Return
Approximately 34 mi | 55 km and 3,850 ft | 1,173 m

Avid Option:

Stokesville to Reddish Knob Loop with Gravel Climb
Approximately 39 mi | 63 km and 4,050 ft | 1,234 m


Hotel Madison

Included Meals:

Breakfast | Lunch | Dinner

For this morning's final ride you will head out to the east of Harrisonburg for a paved loop through the tiny community of Keezletown. Enjoy spinning along Mountain Valley Road with views of Massanutten Mountain before returning to the hotel to prepare for departure. If you’d rather skip the ride, you are welcome to sleep and enjoy a leisurely breakfast. A private Trek Travel shuttle will depart from the hotel at 11:00 AM. You’ll then say farewell to your guides at the Shenandoah Valley Airport at 11:30 AM or the Charlottesville-Albemarle Airport at 12:30 PM.

Today's Ride:

Keezletown Loop
Approximately 18 mi | 29 km and 900 ft | 274 m

Included Meals:



hotel image

Hotel Madison

Harrisonburg, Virginia

Explorer Accommodation | The elegant Hotel Madison is a situated a few blocks from downtown Harrisonburg in the heart of the beautiful Shenandoah Valley. It has a warm and welcoming lobby, full service bar, coffee shop and restaurant, indoor salt water pool, and workout facility. Your Deluxe room features one King or two Queen beds and modern decor along with a television, wifi, Keurig coffee maker, and mini fridge. (If you are driving to the trip, you can park in the adjacent parking garage for $5 per day.)

What's Included

For us, the details matter most

Every moment of a Trek Travel bike trip has more than you could have ever dreamed. More romance. More scenery. More choice. It's the little additions to every Trek Travel cycling vacation that make it truly special. And that's how we help you create more memories.


Trek Checkpoint SLR 7

Take on the challenge of gravel with the knowledge that you are riding the best gravel bike in the business. With a high performance frame designed to be nimble yet stable, and the smoothing effect of rear IsoSpeed technology, it will let you ride with ease on any type of surface. The rugged drivetrain allows you to enjoy smooth and reliable shifting no matter the terrain. It also features Shimano hydraulic disc brakes for predictable and safe stopping power wherever you go. The 45mm tubeless gravel tires will give you confidence to tackle any bump in the road. If you want to escape the concrete, and adventure unpaved, let this bike take you there. Learn More


Trek Electric-Assist Domane+ SLR 7

Take the tailwind with you and leave your limits behind on the all-new Domane+ SLR 7. With a groundbreaking ratio of ultra-lightweight design and electric assist, Domane+ SLR 7 has everything you love in a road bike, with the extra boost to take you farther than ever before. This performance e-road bike will help you on the climbs, hang with the fast group, and venture further on your cycling vacation. So go ahead – take the long way. With Domane+ SLR 7, there’s always room for more distance, more speed, and more fun! Upgrade to the Domane+ SLR 7 on this trip for $399 (3-6 day trips) or $599 (7+ day trips). Available in limited quantities. Please contact a Trip Consultant to check availability. Learn More


  • Four nights of accommodation at a handpicked hotel
  • Two experienced guides to provide local knowledge, support, and camaraderie
  • Daily route support with both guides and our support van
  • Daily breakfast, three lunches, and two dinners
  • Ride a Trek Checkpoint SLR 7
  • Up to three daily route options on riding days
  • Snacks and drinks for each day's ride
  • Trek Travel water bottles to keep
  • Cinch sack day bag to keep
  • Each bike is equipped with a Garmin Edge 1030 GPS computer, a flat pack (containing a tube, levers, and a CO2 cartridge with inflator), front and rear Bontrager Flare R lights, a Bontrager saddle, and Shimano SPD mountain style pedals
  • All gratuities for drivers, local experts, and hospitality staff
  • All luggage transfers and transportation during your trip
  • A digital photo album of your trip
  • Entrance fees for all activities, private tours, and events


  • Upgrade your ride to the Trek Electric-Assist Domane+ SLR 7 specially outfitted with 40mm Bontrager GR1 tires (+$399, subject to availability on select dates.)
  • Trek Checkpoint SLR 7 carbon gravel bike with Shimano GRX electronic shifting and Bontrager carbon wheels
  • Tubeless Pirelli Cinturato Gravel M tires, size 45 mm
  • Trek Travel water bottles to keep
  • Shimano SPD mountain style pedals
  • Bontrager WaveCel helmet
  • Bontrager men's and women's specific saddles
  • Bontrager front and rear Flare R lights
  • In-frame storage containing a tube, levers, and a CO2 cartridge with inflator
  • Garmin Edge 1030 GPS computer
  • Cinch sack day bag to keep
  • Coupon valued up to $500 off a new Trek Bicycle. Your coupon will be delivered via email prior to your trip
  • For the most comfortable ride, you may choose to bring your own pedals, saddle, and helmet on the trip. Your guides will install your gear on the first day during your bike fit.


Guide gratuities are customary and at your own discretion, to recognize service, hospitality, and the little extras that surprise and delight. For this Discover Gravel trip, we suggest a tip for your guides between $150-$200 per guest and, of course, you may choose to give more if your guides made your trip an unforgettable experience. While local currency is preferred, there are other options to make tipping easier. Most guides accept gratuity via PayPal or our staff can help before or after the trip. Gratuities will be divided among the guide team, so feel free to leave your gratuity with whomever you choose at the end of your trip. 
  • Airfare and transportation to and from the trip pick-up/drop-off locations
  • Lodging before and after the trip
  • Personal items purchased during the trip
  • Optional activities not scheduled by Trek Travel
  • On select trips some meals are not included. On these trips, Trek Travel invites you to explore the local cuisine at your leisure.

More Information

Rider Level: 3 - Active?

50 kilometers / 31 miles
249 kilometers / 155 miles
704 meters / 2,315 feet
3,520 meters / 11,550 feet
The unpaved surfaces on our Shenandoah Valley Gravel bike tour are rated as Intermediate. About 50% of the riding is unpaved. You can expect gravel roads that vary from smooth, fast dirt roads to stretches covered with loose gravel. At times, there will be short sections of rougher road that may have chunky gravel as well as some potholes, ruts, divots, and washboard-like surfaces. The paved roads vary from smooth new pavement to rough chip seal. Shenandoah Valley consists of rolling farmland situated between the Blue Ridge and Allegheny Mountains. The terrain on Days 1, 2, and 3 features rolling hills with some short, steep hills mixed in to keep you on your toes. Day 4 in George Washington National Forest is mountainous and you'll choose between a paved climb and descent or a technical gravel climb and paved descent. The final ride is almost entirely paved, making for a relaxing end to the week. Your guides will be able to drive some of the gravel roads with the support van - where this is not possible, the van will be available at strategic points throughout the day. Our Shenandoah Valley Gravel bike tour is best suited for our Type 3 Riders who have experience riding gravel roads and are accustomed to varied gravel conditions and hilly terrain. Type 2 riders who are comfortable riding gravel but are looking for less mileage can ride the short options and utilize the shuttles as indicated. Type 4 Riders will enjoy the extra mileage and climbs the avid route options offer. If you have gravel experience but are concerned about your ability to conquer the mileage and elevation, you may want to try our Domane+ electric-assist bike option.
There are a variety of non-riding options on this trip for riders who want to take the afternoon off or travel companions who want to spend little or no time in the saddle. Some of these options may need to be scheduled before your trip–please contact one of our Trip Consultants for more information. Except as specified in the itinerary, expenses and transportation to these activities are not included in the trip price. Some non-riding options are:
  • Take a hike or drive Skyline Drive in Shenandoah Valley National Park (rental car needed)
  • Tour Luray Caverns (rental car needed)
  • Visit historic Staunton and tour the Frontier Culture Museum among others
  • Visit the Edith J. Carrier Arboretum and Botanical Gardens
  • Go for a hike at one of the many nearby parks, like Riven Rock or Hone Quarry
  • Shop in Harrisonburg
  • Tour the Brethren Mennonite Heritage Center
  • Tour the Quilt Museum
  • Visit Civil War sites
  • Download the Visit Harrisonburg App for more recommendations

See itinerary for specific daily ride distances and elevation options. This is a Discover Gravel trip. Our itineraries are an approximation of our trips. Trek Travel strives to offer every guest a vacation of a lifetime on every trip. On our gravel cycling vacations, Trek Travel seeks to find well maintained, non-technical gravel roads and bike paths; unmaintained roads and roads with ruts or deep or chunky gravel are avoided as much as possible. However, gravel roads are dynamic by nature. Road surfaces change throughout the year depending on maintenance (grading, adding new gravel) and weather, particularly rain. Our guides will be constantly monitoring road conditions and may change the routes as needed to provide the best possible riding experience. In addition, as with all of our trips, at times routes, hotels, activities, etc. listed here may change at the discretion of the trip designer or guides to improve the trip experience.

Averages and totals are calculated from our Today’s Ride options.

Travel Details

How to Get There

Charlottesville-Albemarle Airport (CHO)
11:00 AM
Hotel Madison, Harrisonburg, Virginia

Say Farewell

Charlottesville-Albemarle Airport (CHO)
12:30 PM
Charlottesville-Albemarle Airport (CHO)


We suggest that you arrive at least one day prior to the trip start, which will enable you to adjust to the time zone and minimize the risk of missing the trip start due to flight-related delays. We recommend flying into Charlottesville-Albemarle Airport (CHO) and taking a taxi to Harrisonburg. The drive takes one hour.

You can also fly into Shenandoah Valley Airport (SHD) which is served by Contour Airlines. From here, the drive is 20 minutes by taxi or the SHD Shuttle (540-234-8304). You may also fly into any Washington DC airport and rent a car. The drive is approximately two hours.

Your Trek Travel guides will meet you at the Hotel Madison (710 S Main St, Harrisonburg, VA 22801) at 11:00 AM on the first day of the trip. You and your traveling companions will shuttle 30 minutes to the picnic and bike fit location. Please come dressed in riding clothes and have riding gear in a separate, readily accessible bag. Your main luggage will be stored at the hotel and placed in your room when it is ready.

If you will be late for the pick-up or are going to miss it altogether, please inform your guides. You will receive an email a week before the trip start with their names and contact details. If you cannot reach them, please call our first hotel, Hotel Madison (540-564-0200) and leave a message with your expected arrival time and contact details.

View our pre hotel recommendations


Your guides will offer a shuttle from Hotel Madison departing at 11:00 AM and arriving at Shenandoah Valley Airport at 11:30 AM, then continuing to Charlottesville-Albemarle Airport, arriving at approximately 12:30 PM. Please do not book a flight before 1:00 PM or 2:30 PM respectively in case of for unforeseen delays.

View our post hotel recommendations

Planning For Your Trip

Packing and Weather

Late summer in Harrisonburg is generally warm with some chance of rain, averaging 84F (29C) for the high temperature and 60F (16C) for the low. In September, there is still a chance of rain and it starts to cool down, particularly in mornings and evenings. Temperatures average 78F (26C) for the high and 54F (12C) for the low. October is cooler still with less rain and brilliant fall foliage at 66F (19C) for the average high and 42F (6C) for the low. Light layers and rain gear is always recommended. Don't forget a jacket for cool autumn evenings and mornings. Packing List»

Before and After Your Trip


Before: Richmond, Virginia

The capitol of Virginia is calling! Richmond is a culturally diverse city featuring historic neighborhoods, parks, museums, and the thriving James River. Here a laid-back, eclectic culture has popped up throughout town. Murals cover the walls of local restaurants and shops. Major art museums, like the Virginia Museum of Fine Arts, have drawn national attention. There is also a long list of highlights to see —the Virginia Capitol Building, the Maymont Mansion, the Museum of History and Culture, the Lewis Ginter Botanical Gardens, the Edgar Poe Museum, and various tours available of downtown neighborhoods and historical sights. Food is an art here, too. In fact, National Geographic put Richmond on their list of the world’s—yep, the world’s—“top 10 places to travel for food.” We recommend the following accommodations for your pre-trip hotel:


After: Washington, D.C.

Washington D.C. is home to legendary museums, world-class dining, and charming neighborhoods lined with historic row houses. You can fill countless hours in the Smithsonian Institution’s 17 free museums, galleries, and the National Zoo. Here is home to some of the most famous landmarks in America, including the Lincoln Memorial, the White House, and the Washington Monument. While the city is steeped in history it is also full of wonderful green spaces and trails. Enjoy fresh air in the afternoon strolling city streets and parks then finish your days with world-class dining and crafty beverages made from the cities finest mixologists. We recommend the following accommodations for your post-trip hotel:

Why Trek Travel

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the ultra-smooth Trek Domane SL 7 to the Trek Electric-Assist Verve+, you deserve the best ride on your vacation. Plus, we offer a range upgrade options to take you the extra mile.

Our Guides

Our guides are trained to make your trip magical. They aren't just experts in riding; they're trained in delivering uncompromising service in ways you won't believe. We know that it's the unexpected surprises that make a trip magical. That's why our guides pride themselves on anticipating your needs before you ask.

Your Day. You Decide.

Our vacations are built to deliver the ultimate in flexibility, from extreme relaxers to hard-core roadies. You pick your mileage, itinerary and experiences. We take care of the rest.

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