| 2023 | St. Augustine, FL to Colorado Springs, CO | Howard and Doug Sharp, Fairport, NY | 1916 Hudson |
| 2022 | Warwick, RI, to Fargo, ND | Josh Hull & Trevor Stahl, Roanoke, VA | 1932 Ford Speedster |
| 2021 | San Antonio, TX, to Greenville, SC | Olivia & Genna Gentry, Newnan, GA | 1932 Ford Coupe |
| 2019 | Riverside, CA to Tacoma, WA | Howard and Doug Sharp, Fairport, NY | 1916 Hudson |
| 2018 | Buffalo, New York to Halifax, Nova Scotia | Jeff and Eric Fredette, Beecher, Illinois | 1933 Ford Truck |
| 2017 | Jacksonville, FL to Traverse City, MI | Beth Gentry of Newnan, GA, and Jody Knowles of Tyrone, GA | 1932 Ford Cabriolet |
| 2016 | San Rafael, CA to Moline IL | G.R. Pike and Bobby Hadskey | 1916 Hudson |
| 2015 | Kirkwood, MO to Santa Monica, CA | Howard & Doug Sharp, Fairport, NY | 1916 Hudson |
| 2014 | Maine to Florida | Barry & Irene Jason, Keller, TX | 1966 Ford |
| 2013 | St. Paul, MN to Mobile, AL | Barry & Irene Jason, Keller, TX | 1935 Ford |
| 2012 | Traverse City, MI to Dearborn, MI | Barry & Irene Jason, Keller, TX | 1935 Ford |
| 2011 | Chattanooga, TN to Bennington, VT | Howard Sharp, Fairport, NY & Douglas Sharp, Fairport, NY | 1911 Velie |
| 2007 | Concord, NC to Anaheim, CA | Bob Labine, Phoenix, AZ & Charlie Wheeler, Lone Tree, CO | 1928 Ford |
| 2006 | Philadelphia, PA to San Rafael, CA | David Reeder, Fort Smith, AR & Sawyer Stone, Hot Springs, AR | 1916 Hudson |
| 2005 | Washington D.C. to Tacoma, Washington | Greg Cunningham & Sam Goeppinger, Ponca City, OK | 1928 Ford |
| 2004 | Jacksonville, FL to Monterey, CA | G.R. Pike, Searcy, AR & Bobby Hadskey, Germantown, TN | 1916 Hudson |
| 2003 | Livonia, MI to Daytona, FL | Dick Burdick, San Marcos, TX & Wayne Bell, Winter Springs, FL | 1934 Ford |
| 2002 | San Antonio, TX to Anaheim, CA | Wayne Stanfield, Santa Ana, CA & David Dingman, Nassau, Bahamas | 1934 Ford |
| 2001 | Atlanta, GA to Pasadena, CA | Wayne Stanfield, Santa Ana, CA & Any Massimilla, Stratham, NH | 1934 Ford |
| 2000 | Boston, MA to Sacramento, CA | Dick Burdick, Rosanky, TX & Wayne Bell, Winter Springs, FL | 1916 Hudson |
| 1999 | Marietta, GA to Anaheim, CA | Rex Gardner, Stilwell, KS & Gary Kuck, Lincoln, NE | 1917 Hudson |
| 1998 | Tacoma, WA to Haverhill, MA | Rex Gardner, Stilwell, KS & Gary Kuck, Lincoln, NE | 1917 Hudson |
| 1997 | Sonoma, CA to Jacksonville, FL | Charles Currie, Anaheim, CA & Wayne Stanfield, Santa Ana, CA | 1910 Selden |
| 1996 | Tacoma, WA to Toronto, Canada | Jim Hampton, El Paso, TX & John Sears, Tucson, AZ | 1929 Ford |
| 1995 | Ottawa, Canada to Mexico City, Mexico | Curtis Graf, Irving, TX & Bruce Gezon, Murrysville, PA | 1916 Packard |
| 1994 | Huntington Bach, CA to Wilkes-Barre, PA | Newt Withers, Fountain Valley, CA & Wayne Stanfield, Santa Ana, CA | 1912 Oldsmobile |
| 1993 | Huntington Beach, CA to Norfolk, VA | Alan & Mary Travis, Phoenix, AZ | 1910 Knox |
| 1992 | Charleston, SC to Costa Mesa, CA | Dick Burdick, Rosanky, TX & Wayne Bell, Lake Oswego, OR | 1924 Bentley |
| 1991 | Norfolk, VA to Seattle, WA | Frank & Ray Currie, Anaheim, CA | 1920 Packard |
| 1990 | Westchester, NY to Disneyland | Dick Burdick, Rosanky, TX & Wayne Bell, Lake Oswego, OR | 1924 Bentley |
| 1989 | Norfolk, VA to Disneyland | Dick Burdick, Rosanky, TX & Wayne Bell, Lake Oswego, OR | 1924 Bentley |
| 1988 | Disneyland to Boston, MA | Ron Hayslett, El Paso, TX & Dick Ecelbarger, Tucson, AZ | 1936 Packard |
| 1987 | Disneyland to Walt Disney World, Orlando, FL | Alan Travis, Phoenix, AZ & Wayne Stanfield, Santa Ana, CA | 1916 Mitchell |
| 1986 | Disneyland, Anaheim, CA to New York City, NY | Ron Hayslett, El Paso, TX & Dave Teter, Newark, Delaware | 1936 Packard |
| 1985 | North Hollywood, CA to New York City, NY | Jack Cassan, Oceanside, CA & Elliott Woodward, Seattle, WA | 1914 Dodge |
| 1984 | Universal City, CA to Indianapolis Motor Speedway | Gary Wales, Woodland Hills, CA & John Classen, Burbank, CA | 1936 Bentley |
| 1983 | Knotts Berry Farm, Buena Park, CA to Indianapolis Motor Speedway, IN | Michael & Roger Anderson, Tucson, AZ, Ron Hayslett, El Paso, TX, Dick Ecelbarger, Tucson, AZ | 1941 Cadillac |
