“Discover the Shenandoah”: June 1-7 2025

Tour dates: Sunday, June 1 - Saturday, June 7

At Barren Ridge Vineyards

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: 25-45 miles each day with full support & SAG options

Terrain: all paved surfaces

Cost: $2,395 Double Occupancy or add $500 for single supplement A $200 early bird discount will be applied if you register before 12/31.


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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“Bay to Ocean Tour #1”: May 4-10, 2025