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 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.

New York Finger Lakes Tour 

Ithaca, Geneva & Skaneateles, 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 mid-late July.

BEST OF MADISON TOUR

Delafield, Lake Geneva and Madison, Wisconsin

Come see for yourself why this region is annually rated as one of the top ten bicycling destinations in the country!  Scenic lake views, miles of rolling terrain, a visit to Frank Lloyd Wright’s home Taliesin, a private tour of the Yerkes Observatory (where so many of well known astronomers studied and began their careers), and of course, famous local Wisconsin brews and cheese are highlights of this this awesome Midwestern adventure.  Roll with us through a region that is becoming a foodie paradise!

The Best of Madison Tour is available in May and September.


SOUTHERN SHENANDOAH TOUR

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 and one in September.

 

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.

This tour is not scheduled for 2025, but is available to groups of 8 or 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.

This tour is not scheduled for 2025, but is available to groups of 8 or more.  

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 not scheduled for 2025, but is available to groups of 8 or more.  

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