“Discover the Shenandoah”: June 2-8 2024

Tour dates: Sunday, June 2 - Saturday, June 8

Mural in downtown Staunton

The Ultimate Bicycle Tour of the Shenandoah and Beyond

Are you a lover of cycling, history, culture, wine and hidden gems? Well, we have the perfect experience for you! Join us on our upcoming bicycle tour that will feature hotel stays in some of Virginia's most charming small towns including Charlottesville and Staunton. As an added bonus, we will also be exploring the beautiful Shenandoah Valley region.

We begin our week-long journey in Charlottesville VA where we will pedal through the countryside, you'll have the opportunity to discover back country beauty from your bicycle. Get off the beaten path and uncover scenic wineries, delicious food and historic landmarks that embody the true essence of this region.

With its picturesque streets lined with Victorian architecture, Staunton is perfect for exploring by foot or by bike. The city has a rich history, evident in its well-preserved buildings and landmarks such as the Woodrow Wilson Presidential Library and Museum. Take a stroll through the town's quaint shops and restaurants, and ride your bike along the scenic countryside.

For those looking for an outdoor experience, the Shenandoah Valley offers plenty of options. The Natural Chimneys, located just outside of town, is a must-visit attraction and is the starting point for one of our daily bicycle tours. These stunning rock formations are not only a sight to behold, but also offer hiking opportunities. Nearby Bridgewater is another small town that we explore, with its charming Main Street and access to the North River.

But it's not just about outdoor adventures. These towns also boasts a vibrant arts and culture scene. From local art galleries to live music performances, there is always something happening. You will be amazed!

Discover the Shenandoah Valley and Staunton, Virginia as well as all that the area has to offer!

Ability Level: 2-3(rated moderate to difficult depending on your level of ability. E-bikes are strongly recommended).

Mileage: 25-50 miles each day with full support & SAG options

Terrain: paved surface

Cost: $2,395 Single, $2,245 Double.


  • 3:00pm - Check into our host hotel in Charlottesville

    4:00pm - Rider meeting in hotel lobby

    4:30pm Load up and get shuttled to Charlottesville’s “downtown” area known as the Mall. Explore on your own for a bit then we meet at dinner.

    6:00pm - Dinner (Included as part of the Tour package)

  • 7:00am - Breakfast

    8:15am- Load up in shuttle to bicycle route in the country.

    11:30am - Lunch stop set up along the route.

    4:00pm - Return to hotel for showers, free time

    6:00pm - Dinner (Included)

  • 7:00am - Breakfast

    8:15am - This day is your choice. You can either ride 50 ish miles or take a day off the bike to tour Monticello and visit wineries. We provide all transportation.

    3:30pm - Return to hotel

    5:30pm Load up shuttle to go downtown for free time. Dinner on your own. There are plenty of restaurants to choose from.

  • 7:00am - Breakfast at hotel

    8:15am - Load up luggage and depart for another day of fun riding in back country. Distance will be 25-40 miles with full support and lunch delivered to the course.

    3:00pm- Check into host hotel in downtown Staunton. Once you are settled, you will have some free time to explore the downtown area.

    6:00pm- Dinner with group (Included)

  • 7:00am-8:00am- Breakfast at hotel

    8:15am- Shuttle departs to Natural Chimneys where we will begin our adventure. We will ride to Bridgewater and back. Mileage will be 30ish miles and lunch will be provided in Bridgewater.

    1:00-2:00pm- Riders will return to starting point. If you wish to do a short but steep hike up to the top of the Chimneys, we will load your bikes and wait for you to return. Snacks will be provided for riders waiting.

    3:00pm- Shuttle will take riders back to Staunton for showers and downtime.

    6:00pm- Dinner (On your own) There are several really good restaurants nearby that you can walk to.

  • 7:00am-8:00am- Breakfast at the hotel

    8:15am Ride bikes from hotel into the back country outside of Staunton. Mileage will vary from 25-50 miles depending on which route you want to ride. You will have full SAG support and lunch will be delivered to the course.

    3:00pm- Riders return to hotels for showers and down time.

    6:00pm- Farewell Dinner (Included)

  • 7:00am-8:000am - Breakfast at hotel

    8:15am- Farewell bike tour through the city streets in Staunton. This 15ish mile tour will take you through the campus of Mary Washington College, Gypsy Hill Park and through the historic Thornrose Cemetery. This will be our hilliest ride of all because Staunton is VERY hilly. E-bikes are strongly encouraged.

    10:00am Back to hotel for showers then check out.

Additional Ride Information

What You’ll Get:

  • All-inclusive bicycling vacation including concierge services

  • Exceptional guides who will ensure you’re safe and having a great time

  • All transportation for you and your bike

  • Valet service for your luggage

  • Shuttle service where needed

  • Breakfast each morning

  • Healthy snacks, water and ice at scheduled rest stops

  • Delicious picnic lunches on ride days

  • Free time to stroll, exploring shops, museums, restaurants, breweries and wineries

Things to note:

  • Helmets are required. NO EXCEPTIONS!

  • Please have your bike serviced/setup prior to joining us so that you know your equipment is ready to ride!

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Fall Foliage “Tour 1”: October 17 - 20, 2024