Upcoming Tours

Check out our list of upcoming tours. Click any link below to learn more and register today! Please contact us if you have questions. Don’t be afraid to fill out the wait list form if a tour is sold out. If we get enough interest, we open up a second tour when possible.

Discover the Shenandoah Valley, June 2nd - 8th, 2024 we only have 2 rooms left.

Come find wonder and adventure in the charming small towns of Charlottesville & Staunton, Virginia and its surrounding back country. Nestled in the heart of the Shenandoah, these hidden gem offers a unique blend of history, culture, delicious wines and natural beauty.

Discover Virginia’s Blue Ridge, August 4-10, 2024

Get ready to explore the stunning landscapes and outdoor adventures of Virginia’s Blue Ridge. From biking, hiking and horseback riding in the iconic Blue Ridge Mountains to siting next to a fire pit enjoying the night sky, this trip will be a nature lover’s dream. And don’t forget to indulge in some southern comfort food along the way.

Fall Foliage “Tour 1”, October 17th - 20th, 2024 Sold out

Due to high demand, we are offering back-to-back tours. These routes set you up to see peak fall foliage in a variety of places here in southwest Virginia. Starting in Roanoke, we transport you to two nearby World-Class Rail Trails. The advantage of rail trails is they are located in the mountains but the trails are fairly flat. The Virginia Creeper Trail and the New River Trail with a little “side trip” to Grayson Highlands where wild pony sightings are common. You are set up to receive endless autumn views and discover beautiful mountain scenery. Let our staff show you why travelers from all over visit Virginia’s Blue Ridge Mountains every fall.

Fall Foliage “Tour 2”, October 20th - 23rd, 2024 we only have 3 rooms left

2025 Tour Dates

Please join our wait list below and we’ll contact you as soon as booking begins for these 2025 rides!

Spring Fling, March 23rd - 29th, 2025

Embark on an unforgettable adventure through Virginia's rich history and breathtaking landscapes with our weeklong bicycle tour. Pedal through time as you explore the meticulously preserved streets of Colonial Williamsburg, delve into the beginnings of America at Jamestown Island, and cross the iconic Jamestown-Scotland Ferry. Feel the thrill of the open road as you journey along the scenic Virginia Capital Trail, immersing yourself in the beauty of the countryside.

Bay to Ocean Tour, April 27th-May 3rd, 2025 | May 11th-17th, 2025

Experience the charm and natural beauty of Virginia's Eastern Shore on our weeklong bicycle tour. Pedal through picturesque Cape Charles, with its historic streets and stunning waterfront views. Explore the quaint town of Onancock, where small-town charm meets coastal elegance. Embark on a ferry ride to the timeless Tangier Island, immersing yourself in its unique culture and pristine landscapes. Finally, discover the wild beauty of Chincoteague Island, known for its famous wild ponies and pristine beaches. We conclude the tour with a sunset cruise through the wildlife refuge. Due to high demand in 2024, we will offer two tours in 2025.

Discover the Shenandoah Valley, June 1st-7th, 2025

This weeklong journey through the heart of Virginia's storied landscapes and vibrant communities with our captivating bicycle tour. We will explore the charming streets of Charlottesville, where history meets modern allure amidst the backdrop of the Blue Ridge Mountains. Explore the cultural gem of Staunton, with its quaint downtown and rich artistic heritage. Then, pedal through the breathtaking Shenandoah Valley, where rolling hills and picturesque farmland paint the perfect backdrop for your adventure. Join us for a week of scenic cycling, cultural immersion, and unforgettable memories in one of Virginia's most iconic regions.

We take one day off the bicycles to choose between a journey through history at Monticello, the iconic home of Thomas Jefferson, where you'll wander the grounds and explore the legacy of one of America's founding fathers, or opt for a leisurely day of winery hopping aboard our designated van. Savor the flavors of local vineyards nestled amidst the stunning backdrop of the Blue Ridge Mountains, sampling exquisite wines and enjoying the tranquil ambiance of Virginia's wine country. Whichever experience you choose, it promises to be a day of relaxation and discovery in addition to your unforgettable cycling adventure.

Discover Southwestern Virginia Rail Trails & More, June 22nd-28th, 2025

Embark on a weeklong cycling odyssey through the scenic wonders of Southwestern Virginia with our unforgettable bicycle tour. Pedal along the tranquil waters of the New River Trail, where lush forests and towering cliffs create a breathtaking backdrop for your journey. Traverse the historic Virginia Creeper Trail & the Greenbrier Trail, immersing yourself in the charm of quaint mountain towns and verdant landscapes. Explore hidden gems along winding back roads, discovering the rich culture and natural beauty of the region. Cap off your adventure with a ride through the picturesque landscapes of Burke's Garden, known as 'God's Thumbprint,' where rolling hills and fertile farmland stretch as far as the eye can see. Join us for a week of unparalleled exploration, adventure, and discovery in the heart of Southwest Virginia.

Discover Virginia’s Blue Ridge Parkway, August 10th-16th, 2025

Enjoy a weeklong cycling expedition through the majestic beauty of the Blue Ridge Parkway and beyond with our thrilling bicycle tour. Traverse the iconic Blue Ridge Parkway, where sweeping vistas and winding mountain roads offer unparalleled views of the Appalachian landscape. Experience the serenity of the Peaks of Otter Lodge nestled amidst the rolling peaks, where comfort meets adventure in the heart of nature. Ride on back roads of Bedford and Campbell Counties, steeped in history and surrounded by the stunning scenery of the Virginia countryside. Join us for a week of exhilarating cycling, scenic exploration, and unforgettable memories along the storied routes of the Blue Ridge Parkway and beyond.

GAPCO (Great Allegheny Passage - C&O Canal), September 28th-October 4th, 2025

Join us for the ultimate adventure from the bustling cityscape of Pittsburgh to the iconic monuments of Washington DC on our weeklong bicycle tour. Kickstart your journey along the picturesque Great Allegheny Passage Trail, winding through lush forests, charming towns, and historic sites as you pedal towards the majestic Appalachian Mountains. Then, seamlessly transition onto the serene C&O Towpath, where the tranquil waters of the Potomac River guide your path towards the nation's capital. Experience the beauty of nature and the thrill of discovery as you traverse the 335 miles of scenic trails, immersing yourself in the rich heritage and breathtaking landscapes along the way. Join us for a week of unforgettable cycling, adventure, and exploration from Pittsburgh to Washington DC.

Fall Foliage World Class Rail Trails, October 12th-18th, 2025 | October 19th-25th, 2025

Embark on a weeklong cycling odyssey through the scenic wonders of Southwestern Virginia with our unforgettable bicycle tour. Pedal along the tranquil waters of the New River Trail, where lush forests and towering cliffs create a breathtaking backdrop for your journey. Traverse the historic Virginia Creeper Trail and the Greenbrier Trail, immersing yourself in the charm of quaint mountain towns and verdant landscapes. Explore hidden gems along winding back roads, discovering the rich culture and natural beauty of the region. Cap off your adventure with a ride through the picturesque landscapes of Burke's Garden, known as 'God's Thumbprint,' where rolling hills and fertile farmland stretch as far as the eye can see. Join us for a week of unparalleled exploration, adventure, and discovery in the heart of Southwest Virginia.