North Carolina to Lynchburg

US 29 enters Virginia in Danville from North Carolina. While US 29 Business (US 29 Bus.) continues into Danville, US 29 joins the Danville Expressway and US 58 around the east side of Danville, entering Pittsylvania County and remerging with the business route north of town in Blairs. The interchange where US 29 joins US 58 has ramps that enter North Carolina and ramps that enter Virginia, complete with welcome signs from each state. There is a cloverleaf ramp that dips into North Carolina from Virginia and then crosses the state lines back into Virginia. Along the southeastern quadrant of the Danville Expressway between the North Carolina US 360, the route is designated as part of unsigned State Route 785 (SR 785) for 7.39 miles (11.89 km).^[5] Created c. 2000, SR 785 is numbered in contradiction to the conventional system of numbering in the state, where primary routes are numbered less than 600 and secondary routes at or above this number. It is numbered as such because it is part of the planned I-785, which will run south along US 29 to I-85 in Greensboro, North Carolina, and is only one of two routes of this type. The other is SR 895 in Richmond for similar reasons.

Lynchburg to Charlottesville

US 29 then continues north where it has business routes for Chatham, Gretna, and Hurt while bypassing them before entering Campbell County.

The next major city is Lynchburg. US 29 joins the US 460 bypass and US 501 east of Lynchburg, splitting from them just before entering Amherst County. US 29 again bypasses Madison Heights and Amherst as an expressway, enters Nelson County, passes the town of Lovingston, and enters into Albemarle County.

Charlottesville to Warrenton

For the next few miles of US 29's route north of Lovingston, it enters mountainous terrain in the far western Piedmont close to the Blue Ridge Mountains. Several miles later, the route then continues north to Charlottesville, intersecting I-64 and bypassing downtown Charlottesville. US 29 rejoins its congested business route just north of downtown, continuing north as a six-lane road through Charlottesville's business district. Past Charlottesville, it converts back to four lanes and continues through Greene and Madison counties and then turns northeast toward Culpeper. US 15 joins US 29 around Culpeper and heads to Warrenton, entering Northern Virginia.

Warrenton to Washington DC

US 29/US 15 is joined by US 17 south of Warrenton in Fauquier County and continues around the town, with US 17 splitting off. US 29/US 15 continues mostly eastward to Gainesville where US 15 splits and US 29 intersects I-66 for the first time. US 29 continues into Fairfax County, where it passes along the boundary of the city of Falls Church, where the road has two different names. The portion of the street running northbound is located in the city of Falls Church is called Washington Boulevard and has different street addresses than the other side running southbound in Fairfax County, where it is named the Lee Highway. The road continues into Arlington, having intersected I-66 five more times before crossing into Washington DC.

Gainesville Interchange

The Gainesville Interchange project took place at the interchange between the Lee Highway (US 29) and I-66 at the junction with Linton Hall Road (SR 619) starting in July 2011, with board planning on it dating back to 2006. The project was worth $230 million (equivalent to $307 million in 2023^[9]) and included interchanges at many other heavily traveled roads in the area due to the rapid growth in development in Gainesville and Haymarket, along with it being a major area drivers departure off of I-66 to travel towards other major cities along the Lee Highway, such as Charlottesville. The reasoning for this inclusion of other interchanges is because of the lack of road development to accommodate the new heavy traffic in the area. The plan included a single-point urban interchange design and bridges over train tracks to ease traffic flow on the Lee Highway onto I-66. The Lee Highway was also widened around the interchange to combat this issue. What was once a two-lane country road is now a four-lane suburban highway. Land was acquired by the Virginia Department of Transportation (VDOT) at the intersection of US 29 and Linton Hall Road/SR 619. The entire project was completed and opened to the general public on July 9, 2015.

Charlottesville Interchange (Rio Road)

The Charlottesville Interchange project took place at the intersection of US 29 and Rio Road/SR 631, with construction starting in mid-2015 and ending in December 2016.^[10] A diamond interchange was built, with two lanes from each direction of US 29, deemed the "local lanes", exiting from main traffic and meeting Rio Road at a traffic signal. The project cost $69.7 million (equivalent to $86.8 million in 2023^[9]).

Lynchburg Interchange

The Lynchburg Interchange project took place at the intersection of US 29/US 460/US 501 and Odd Fellows Road, with construction starting in January 2016 and ending in August 2018. A diamond interchange was constructed at a cost of about $30 million (equivalent to $35.9 million in 2023^[9]). The interchange was built to reduce congestion on Candlers Mountain Drive/US 501 and to make access to Mayflower Drive/SR 128 easier.^[11][12] As part of the construction, roundabouts were constructed on Odd Fellows Road at its intersection with Mayflower Drive, west of the interchange, and Top Ridge Road, east of the interchange.^[13]

Charlottesville Bypass

A western US 29 bypass around Charlottesville was originally proposed in 1979. Engineering and environmental work on the project began in late 1984, and the location was approved by the Commonwealth Transportation Board in 1990.

Acquisition of right-of-way for the project began in 1991 and continued until 2001. No additional right-of-way has been purchased since then. VDOT owns 36 properties that are currently leased and occupied.

The bypass was projected to be 6.2 miles (10.0 km) long, from the US 250 bypass to current US 29 north of the South Fork Rivanna River. It would have been two lanes in each direction with no other exits, to decrease possible interruption of commercial and residential growth in the area.

In 1998, a lawsuit was filed challenging the project, alleging that the environmental impact review of the project violated the National Environmental Policy Act (NEPA). In 2001, the federal court ruled in favor of VDOT on the suit but required the agency to complete a supplemental environmental impact statement (EIS) addressing the road's impacts on the South Fork Rivanna Reservoir and the mitigation to minimize those impacts. That document was completed and accepted by the Federal Highway Administration (FHWA) in 2003.

In 1996, the Charlottesville-Albemarle Metropolitan Planning Organization (MPO) inserted language into its Transportation Improvement Program that prevented additional funds from being allocated to construction of the Western Bypass. That language was removed by the MPO Policy Board in July 2011.^[14]

All activities on the US 29 Charlottesville Bypass project were suspended in March 2014 following notification from the FHWA that a new supplemental EIS would be required before the environmental process could be completed. The new supplemental EIS was required due to the history of litigation and controversy associated with the project.^[15]

Charlottesville Interchange (Hydraulic Road)

The Charlottesville City Council voted on May 6, 2018, to add a long-range development plan for a diamond interchange at the intersection of US 29 and Hydraulic Road/SR 743 at an estimated cost of $63 million to $80 million (equivalent to $75.3 million to $95.6 million in 2023^[9]).^[16]