Segment 1st State
Days 11 (June 9 - 19)
Mileage (% of total) 595.2 mi (13%)

A quick look

  • Expected to be among prettiest but most difficult state.
  • A potpourri of quiet back roads, magnificent planations, scenic valleys, rolling hills, steep mountains, and a lushness that gives everything a special green hue.1
  • This is only one of four states officially called commonwealths (besides Kentucky, Massachusetts, and Pennsylvania) and is home to eight U.S. Presidents.
  • Of the ten states this is only one of two that I have been to before (Missouri is the other).
  • State web site


  • The eastern portion of the state has moderate vertical development.
  • Overall this state has the most elevation gain which will be particularly taxing early in the journey.
  • The roads in the Appalachians can be quite steep and there is a lot of "up and down" as compared to the long, gradual passes in the Rockies.


  • Virginia is usually very hot and humid in the summer. Since I'm starting in early June there will be some relief.
  • June typical high: low 80s
  • June typical low: mid 60s
  • Read more

There is a tradition among cross country cyclists to dip the rear wheel of the bicycle in the ocean at the beginning of the trip and the front wheel at the end. I'll start my journey at the mouth of the York River where it dumps into the Atlantic. It is here that I'll ceremoniously dip either the bike or trailer tire in the ocean. E-mail me to vote on which you think is appropriate. My journey begins at 2:00pm at the Yorktown Memorial on June 9 - everyone is invited to see me off!

The TransAmerica route officially begins at Victory Monument in Yorktown. This spot marks the location where, in1781, British commander Lord Cornwallis surrendered, marking the end of the seven year Revolutionary War.

From Yorktown I will ride to Williamsburg and Jamestown, known as Virginia's Historic Triangle. This early part of the journey along the Colonial Parkway is ripe with history. Williamsburg is home to a 173 acre recreation of 18th century colonial America. In Jamestown I'll see the remains of the first permanent English settlement in America.

Other attractions along the route

1Donna Lynn Ikenberry in Bicycling Coast to Coast, 1996
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Updated 2.6.03
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Lawrence J. Flint