Hilly Bicycle Tours

Hills: If you love them, we've got them. Come climb with us. We'll provide the support you need to make it happen. We offer hilly tours through Wisconsin's capital city and through the mountains of northern Virginia. The following is a complete list of tours that range from rolling hills to big mountains.

If hills and challenging climbs aren't your thing, we also offer a number of flat, easy rides.



Madison, Delafield and Lake Geneva, Wisconsin

An inn-to-inn cycling tour of the southern Wisconsin and its beautiful capital city. Explore this hilly region dotted with lakes, quirky towns, craft breweries and more. Spend 6 days and 5 nights of lake views and miles of rolling terrain enjoying beautiful water views, vibrant downtown Madison, and Frank Lloyd Wright's Taliesin.

This tour is available for custom groups and self-guided tours in 2021.  Call 888-251-3206 to find out more.


New York Finger Lakes Tour 

Ithaca, New York

This is a moderately hilly tour around the lakes of Central New York. Explore the highest waterfalls east of the Rockies, cascades, glens, colleges, hamlets, valley farms, quaint towns and steep hillsides dotted with vineyards. Spend 6 days and 5 nights cycling through the rolling hills of NY, enjoying spectacular waterfall hikes and a Finger Lake wine tasting along the way.

There are two New York Finger Lake tours available in late July.


Adirondacks and Vermont Tour

Saratoga Springs and Chestertown, New York; Brandon and Manchester, Vermont

An inn-to-inn cycling tour of the southern Adirondacks and Southwest Vermont. The terrain is hilly, with a few longer, more challenging climbs, but your hardwork will pay off. Explore some of the prettiest areas of Vermont and New York: pristine Adirondack lakes, verdant Vermont farmland, and the upper Hudson River Valley. Savor beautiful Adirondack lake views and expereince vibrant Saratoga Springs, NY on this 6 day, 5 night tour. 

This tour is available for custom groups and self-guided tours in 2021.  Call 888-251-3206 to find out more.


Virginia Blue Ridge TOUR

Roanoke, Blacksburg & Floyd, Virginia

Come ride the Blue Ridge Mountains.  Southwestern Virginia is home to beautiful sections of the Blue Ridge Parkway, the charming arts community of Floyd, bustling Blacksburg and mile after mile of beautiful road cycling. Although hilly and challenging, each day will include rides through some of the most historic and iconic sections of the Blue Ridge Parkway. Spend 5 days and 4 nights experiencing spectacular scenery and biking.

There is one Virginia Blue Ridge tour available in September.



Staunton, Lexington & Bath County, Virginia

This is a more challenging road bicycling tour of the Southern Shenandoah Valley, Allegheny Mountains and Blue Ridge Parkway. Experience breathtaking Blue Ridge overlooks, pastoral valley farm roads, and winding mountain passes on this incredibly diverse tour. Spend 5 days and 4 nights winding through Virginia's Allegheny & Blue Ridge Mountains and the Great Valley Between. 

There is one Southern Shenandoah tour available in May.


Middle Tennessee Tour

From Murfreesboro to Smithville

Middle Tennessee is a beautiful area of rolling foothills and lightly traveled back roads. Known for the Home of Country Music and the Jack Daniels Distillery, there is a lot more for the road cyclist to savor along the way. From Historic Murfreesboro's charming downtown to Upper Cumberland's waterfalls, caverns and Great Falls Dam, spend 6 days and 5 nights riding through middle Tennessee's rural heartland.

There is one Middle Tennessee tour available in late April and one tour available in September.


NC Horse Country Tour

From Chapel Hill to Southern Pines, North Carolina

A bicycle tour of North Carolina's central heartland, including Chapel Hill, the Uwharries and the Sandhills, offering beautiful rural scenery, fine dining, and charming accommodations. No mountains here, just large rolling hills. This is a great springtime tour for getting those legs in shape for the riding season. Experience an authentic "southern hospitality" for 5 days and 4 nights in NC's Heartland.

There is one NC Horse Country tour available in April and one tour available in October. 


Still not sure if hills are your thing? Check out the flat tours we offer.