TransAm Westward

The Route Where it all Began
Barry Gregory
Price :
Surface :
Duration :
93 days
Support :
Self Contained
Difficulty :
Level 5

Thousands of cyclists have pedaled the 4,253-mile TransAmerica Trail and will tell you they captured a lifetime’s worth of memories along their tour. For many traveling cyclists who haven’t yet experienced the TransAm, it remains the holy grail of American bicycle tours.

Starting in Virginia, you’ll pedal westward through rolling hills into the steeper climbs of Kentucky, Illinois, and Missouri. After the windswept plains of Kansas and eastern Colorado, the remainder of the journey is primarily through the Rocky Mountains. You and your fellow group members can make this trip a unique experience like no other. Daily tasks, including shopping and camp cooking, are also shared on a revolving basis. Each day, you’ll be free to ride at your own pace, shoot photos, chat with locals, and search out the best swimming hole in every state.

Photos by Aaron Teasdale | Russ Roca | Greg Siple

There are no scheduled departures for this tour.

"Our tour leader was excellent and the other cyclists became my friends. A wonderful experience, and I can't wait to do my next tour."


Week 1. Williamsburg to Charlottesville, Virginia

From Yorktown, Virginia, we’ll ride through the welcoming terrain of the Tidewater region, a rolling plain that rises gradually to meet the Virginia Piedmont and its somewhat steeper hills. A layover day in Charlottesville will give us time to tour the University of Virginia’s magnificent campus, designed by Thomas Jefferson. Outside of town, we can also visit Jefferson’s Monticello, with its resplendent gardens and hilltop location providing long-range views of the surrounding countryside.

Week 2. Charlottesville to Damascus, Virginia

In Afton we’ll ride by the Bike House, the longtime home of June Curry, the world-famous “Cookie Lady,” who hosted more than 14,000 touring cyclists from 1976 until her death in 2012. From there we’ll inch our way up to the Blue Ridge Parkway and bicycle along that legendary roadway until beginning the four-mile descent into the town of Vesuvius. From here to Christiansburg, the route closely parallels the Great Wilderness Road, an ancient Native American trail at the base of the Blue Ridge that Stonewall Jackson marched troops along during the Civil War. The week will end a rest day in the notorious Appalachian Trail town of Damascus where you’ll likely meet travellers on a different kind of epic adventure.

Week 3. Damascus to Harrodsburg, Kentucky

We’ll cross into Kentucky at Breaks Interstate Park, one of only two parks in the nation shared by two states. The 4,500-acre preserve holds an enchanting expanse of forested mountains, as well as the “Grand Canyon of the South,” created by the erosive action of the Russell Fork of the Big Sandy River. Prior to crossing the state line, we can sign the “Across State Ride” book that Virginia officials are using to compile statistics they hope will one day result in improvements to U.S. Bike Route 76, established in 1982 and now part of the growing U.S. Bicycle Route System. Ahead lie the hilly, winding, and often densely vegetated roadways of the eastern Kentucky Appalachians. We’ll ride just south of the Tug River Valley, which separates West Virginia and Kentucky, and where the long-running McCoy-Hatfield Feud erupted at the end of the Civil War. We’ll take a layover day in Berea to learn more about the feud and mountain culture in general at the Appalachian Museum and nearby Berea College.

Week 4. Harrodsburg to Carbondale, Illinois

Leaving the challenging Appalachians behind, the Bluegrass region of central Kentucky will greet us with its verdant pastures and postcard-worthy horse farms delineated by neat white fences. After continuing through western Kentucky and the communities of Harrodsburg, Utica, and Marion, we’ll cross the wide Ohio River into southern Illinois, where we’ll camp at Dixon Springs State Park. The ridges and valleys of the small mountain range known as the Little Ozarks will show us the way to Carbondale, home to Southern Illinois University and another perfect place for a layover day.

Week 5. Carbondale to Marshfield, Missouri

In Chester, Illinois, we’ll cross the mighty Mississippi on the Chester Bridge, a truss bridge that appeared in the opening scene of the 1967 movie In the Heat of the Night. We’ll then begin tackling the notoriously steep and seemingly never-ending hills of the Missouri Ozarks. Camping for a night at Johnson’s Shut-Ins State Park, we’ll explore the narrow gorges carved by streams into 1.5-billion-year-old igneous rhyolite. In Eminence we might set our bicycles aside for the morning in order to enjoy a mellow canoe float down the crystal waters of the spring-fed Current River, a component of the Ozark National Scenic Riverways.

Week 6. Marshfield to Sterling, Kansas

We’ll spend our first night in Kansas, the Jayhawk State, in Pittsburg, which was named after Pittsburgh, Pennsylvania, in 1876. We’ll curse and praise the ever-present Kansas wind, depending upon whether it’s blowing at our backs or in our faces as we pedal amidst endless fields of grain and sunflowers. When we’re still miles from Eureka, Newton, and a host of smaller towns, we’ll spot the communities’ tall grain elevators standing like sentinels above the endless plains.

Week 7. Sterling to Pueblo, Colorado

As we make our way through central and western Kansas, we’ll leave the humidity behind, entering the arid West. We’ll start the week in Great Bend, KS, named after its location at the "great bend" in the Arkansas River where the river's course turns eastward. You may be surprised that the mountains don’t jut into the sky immediately after we cross into Colorado — in fact, there’s quite a long piece of Kansas-like terrain separating the interstate border and the Rockies. The vibrant city of Pueblo marks both the approximate halfway point of our cross-country adventure and the start of the Rockies.

Week 8. Pueblo to Walden, Colorado

We’ll relish a layover day outside Cañon City at Royal Gorge, the Grand Canyon of the Arkansas. The river is spanned by the world’s highest suspension bridge over water. From there we’ll make our way through the spectacular wide-open countryside of South Park before climbing to the apex of the TransAmerica Trail, 11,542-foot Hoosier Pass. You’ll remember this climb and the descent that follows! At the base of the downhill lies Breckenridge and greater Summit County, one of Colorado’s recreation hot spots for both summer and winter sports.

Week 9. Walden to Colter Bay, Wyoming

Just north of Walden, we’ll ride into windy Wyoming and overnight in the fun mountain town of Saratoga. There we can soak our weary bones in the free, community-owned Hobo Hot Pool. Afterwards we’ll begin the high and dry ride through the sagebrush- and pronghorn-filled Great Divide Basin. From Lander to Dubois, where we’ll stop for a visit to the National Bighorn Sheep Interpretive Center, we’ll alternate between big mountains and broad valleys. After climbing up and over Togwotee Pass, we’ll free-fall into world-famous Jackson Hole and spin through spectacular Grand Teton National Park.

Week 10. Colter Bay to Dillon, Montana

We’ll mosey around the western town of Jackson, checking out the elk-antler arches that mark the four corners of the Town Square, and straddle leather saddle stools in the Million Dollar Cowboy Bar. From the quaint community of Wilson, we’ll climb out of Jackson Hole over the unforgettably steep Teton Pass and descend into Teton Valley, Idaho. After enjoying the eight-mile-long rail-trail connecting Victor and Driggs, we’ll proceed north through undulating potato and barley country to Ashton, “Seed Potato Capital of the World.” If your tires and spirit are up to it, you can ride the 40 miles separating Tetonia and Ashton on the gravel-surfaced Tetonia-Ashton Rail-Trail. From there, it’s on to West Yellowstone, Montana. After a layover day and an optional side trip into Yellowstone National Park, we’ll ride alongside the trout-rich waters of the Madison River to Ennis. From there we’ll climb into Virginia City, an evocatively renovated Victorian frontier town that was the site of a major 1860s gold strike and, for a short time, the capital of the Montana Territory.

Week 11. Dillon to Grangeville, Idaho

We’ll then push on to the high lonesome of the Big Hole Valley, over Chief Joseph and Lost Trail passes, and then into the bustling Bitterroot Valley. We’ll enjoy a well-deserved layover day in Adventure Cycling’s hometown of Missoula, an oasis of culture and entertainment. Tracing the tracks of Lewis and Clark’s Corps of Discovery, we’ll cross Lolo Pass and re-enter Idaho, riding beside the Lochsa River as it cuts through an immense wilderness expanse.

Week 12. Grangeville to Mitchell, Oregon

After descending the twisty switchbacks along Old Route 95, you’ll find yourself immersed in the White Bird Battlefield National Historic Park, the location of the first battle of the Nez Perce War where the Nez Perce defeated the U.S. cavalry and escaped to find safety on June 17,1877. Next, the cool little town of Riggins will provide us with the option of splashing our way on a half-day rafting trip through the whitewater rapids of the Salmon River’s main fork. We’ll cross the Snake River into Oregon near Hell’s Canyon, the deepest river gorge in North America. We’ll take a layover day in Baker City, rich with gold-mining lore.

Week 13. Mitchell to Eugene, Oregon

After crossing a series of relatively minor mountain ranges and visiting towns like Mitchell, Prineville, and Sisters, we’ll have the thrill of crossing the Cascade Range through volcanic McKenzie Pass. We’re getting close to the Pacific Ocean and the end of our three-month-long continent crossing. The final three days of our grand tour by velocipede consist of a beautiful route from Coburg to the coast by way of the covered bridges of the Alsea River Valley. We’ll dip our wheels in the Pacific at Beachside State Park. After riding south down the coast to Florence, we’ll enjoy a bittersweet celebration dinner. The following morning we’ll return to Eugene for a formal wrap-up and farewells before heading back to the real world.


Additional Details
Start Location:
Williamsburg, VA
End Location:
Florence, OR
Richmond Intl. (RIC), Eugene Airport (EUG)
Total Days:
Riding Days:
Layover Days:
Average Daily Mileage:
Shared cooking
Level 5
Elevation Alert:
High Point: 11,535'
Restricted Bike Type:
eBike, eTrike