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The Terrible Two course has changed in many ways—some minor, some significant—over the years. In the interest of keeping things relatively simple, we have grouped our course records into two categories: Short Course and Long Course.

The Long Course includes a loop north from Skaggs Springs-Stewarts Point Road through Annapolis to Sea Ranch. This was the standard course (with assorted variations) through 1994, with an anniversary reprise of the course in 2005. The distance for that course varied from 208 to 211 miles, depending on other variations elsewhere around the course. 

The Short Course, introduced in 1995, heads straight west to the coast on Skaggs Springs-Stewarts Point Road, eliminating the Annapolis loop but introducing the so-called Rancheria Wall. The distance for this course has varied from 198 to 200 miles. It now stands at almost exactly 200 miles. A significant change was introduced in 2016: the first 69 miles of the route were reconfigured to stay out of Napa Valley.

  Short Course fastest times Year Time 
       
Men      
  Levi Leipheimer 2015 10:00
  Brian Anderson, Mark Reidy 2002 10:50
  Brian Anderson 2004 10:59
  Brian Anderson 2006 11:06
  Brian Anderson 2007, 2009 11:11
       
Women      
  Catharina Berge 2002 11:35
  Brenda Phelps 2007 12:05
  Brenda Phelps 2006 12:11
  Laura Stern 2002 12:16
  Muffy Ritz 1995 12:25
       
Tandem, Men      
  Paul McKenzie/Ray Plumhoff 2004 11:20
  Paul McKenzie/Ray Plumhoff 1996 11:52
       
Tandem, Women      
  Liz Galler/Kathlynn Beranek 1997 16:15
       
Tandem, Mixed      
  Paul McKenzie/Catharina Berge 2003 11:42
  Paul McKenzie/Sara Ballantyne 1997 12:21
  Mark Patten/Cindi Staiger 1996 13:18
       
Recumbent      
  James Kern 2007 13:19
       
Fixed Gear      
  Steve Smead 2009 13:25
  Steve Smead 2011 13:56
  Ken Eichstaedt 2004 15:17
       
Long Course fastest times      
       
Men      
  Victor Czech 1994 11:19
  Chaz Fetrow 1994 11:46
  Brian Anderson 2005 11:47
  Paul Solon 1994 11:55
  Jim Daniel 1989 12:01
       
Women      
  Lea Brooks 1984 14:06
  Elaine Mariolle 1986 14:29
  Kristen Scheller 1994 14:30
  Linda Bogdanoff (Fluhrer) 1990 14:37
       
Tandem, Men      
  Paul McKenzie/Ray Plumhoff 2005 11:58
       
Tandem, Mixed      
  Tom and Cindy Long 2005 13:38
  Tom and Terry Dempster 1981 13:50
       
Recumbent      
  Eric House 1994 12:53
       
Oldest finishers, either course      
  John Abbe 1998 71
  Gerd Rosenblatt 2004 70
       
Youngest finishers, either course      
  Lars Norlund 1995 15
  Jon Moore 1993 16

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