1975: The Commonwealth Transportation Board designates Route 5 as the Commonwealth’s second Virginia Byway.

1991: House Document No. 44 (Report of the Virginia Department of Transportation on Route 5 Corridor Study to the Governor and The General Assembly of Virginia) recommends including bicycle lanes on Route 5 and preserving the scenic character of Route 5 to the fullest extent possible.

1996: The Virginia Department of Transportation (VDOT) issues a request for proposals to conduct a study on the feasibility of constructing a bicycle path between Williamsburg and Richmond, adjacent to Route 5.

1997: VDOT selects Vanasse Hangen Brustlin, Inc. (VHB) to perform the feasibility study.

1999: VHB completes the feasibility study, which includes a preferred alignment for a multi-use trail along Route 5.

2003: Governor Mark Warner’s Secretary of Transportation, Whitt Clement, makes the Route 5 multi-use trail a priority and obtains initial funding. VDOT begins a survey of the proposed trail.

2004: Federal enhancement funds are received for the first two segments of the trail in James City County. Preliminary design begins.

September 2004: The Virginia Capital Trail Foundation is formed as a nonpartisan advocacy partner to provide Trail expertise, to raise public awareness of the Trail, and to seek funding and contributions to enhance and promote the Trail.

2005: Richmond Mayor Douglas Wilder endorses the Trail. Negotiations with private and commercial landowners proceed.
July 2005: Governor Mark Warner delivers the keynote address in Jamestown for the groundbreaking of the Greensprings Road portion of the Virginia Capital Trail.

2006: Governor Tim Kaine delivers the keynote address in Jamestown for the opening of the Greensprings Road portion of the Virginia Capital Trail, and pledges to have all the construction funding allocated before he leaves office.

2007: MeadWestvaco pledges $300,000 to the Virginia Capital Trail Foundation.

August 2007: Mayor Douglas Wilder delivers the keynote address for the groundbreaking of the Richmond Riverfront Section of the Trail.

2008: Ground is broken on the 8-mile Charles City County portion of the trail.

April 2009: Designs for a Trail-wide signage system and the first trailhead in James City County are approved.

April 2009: Dominion pledges $110,000 to the Virginia Capital Trail Foundation.

December 2009: Gov. Tim Kaine delivers the keynote address at the opening of the Richmond Downtown Phase 1 portion of the Trail.

March 2010: Virginia First Lady Maureen McDonnell is the keynote speaker for the ribbon cutting of the Jamestown Trailhead.

May 2012: Virginia Secretary of Natural Resources Doug Domenech is the keynote speaker for the groundbreaking of the Sherwood Forest phase of the Trail.

October 2013: Richmond Mayor Dwight Jones is the keynote speaker for the opening of the Great Shiplock Park trailhead at the western terminus of the Virginia Capital Trail.

October 2014: Virginia First Lady Dorothy McAuliffe delivers the keynote address and cuts the ribbon at the opening of the Sherwood Forest phase of the Virginia Capital Trail.

October 2015: Virginia Governor Terry McAuliffe delivers the keynote address and cuts the ribbon at the opening of the entire Virginia Capital Trail in the Virginia Holocaust Museum.