When approaching Charlottesville from any direction, there are a number of signs which mark the route to James Monroe’s Highland.
From I-64 (from Staunton/Waynesboro or Richmond): Take Exit 121 (heading east the exit is 121-A) onto Route 20 South. At the second traffic light, turn left onto Route 53. Continue on Route 53 past Michie Tavern, Monticello, and a sharp bend to the right. After Jefferson Vineyards, turn right onto State Route 795—James Monroe Parkway. Continue ½ mile. James Monroe’s Highland is on the right.
From Downtown Charlottesville: Take Route 20 South (Monticello Avenue) from downtown. Continue under I-64. Turn left on Route 53 at the second traffic light and continue past Michie Tavern, Monticello, and a sharp bend to the right. After Jefferson Vineyards, turn right onto State Route 795—James Monroe Parkway. Continue ½ mile. James Monroe’s Highland is on the right.
From Northern Virginia on I-66: From I-66, take Exit 43-A onto Route 29 South. Continue south on Route 29 approximately 90 miles. Approaching Charlottesville, follow signs for the 29/250 Bypass which will take you west around the city. From the 29/250 Bypass, turn onto I-64 East toward Richmond, then take Exit 121A onto Route 20 South. After ¼ mile turn left onto Route 53 and continue past Michie Tavern, Monticello, and a sharp bend to the right. After Jefferson Vineyards, turn right onto State Route 795—James Monroe Parkway. Continue for ½ mile. James Monroe’s Highland is on the right.
From Lynchburg: Take Route 29 north to I-64. Take I-64 East toward Richmond, and take Exit 121-A onto Route 20 South. At the second traffic light turn left onto Route 53, and continue past Michie Tavern, Monticello, and a sharp bend to the right. After Jefferson Vineyards, turn right onto State Route 795—James Monroe Parkway. Continue ½ mile. James Monroe’s Highland is on the right.
From Northern Virginia on I-95: From I-95 travelling south, exit at Fredericksburg onto Route 3 heading west. Continue on Route 3 then turn left onto Route 20 South. At Orange, turn left onto Route 15. At Gordonsville, enter the roundabout and exit onto VA-231. Continue past Cismont (where VA-231 becomes VA-22) and Keswick, then turn left onto Route 250. At the first light turn right onto North Milton Road, cross the Rivanna River, then turn right onto Milton Road. Three miles later, Milton Road intersects Route 53 opposite St. Luke’s Church at Simeon. Turn left onto Route 53, drive past Jefferson Vineyards, then turn right onto State Route 795—the James Monroe Parkway. James Monroe’s Highland is located ½ mile on the right.
From Palmyra/Fluvanna County: Take Route 53 toward Charlottesville, then turn left onto State Route 795—the James Monroe Parkway. Continue ½ mile. James Monroe’s Highland is on right.
The “Journey Through Hallowed Ground” Route (a scenic and historic drive following Routes 15 and 20): From the Fredericksburg area—which features the Civil War battlefields of Fredericksburg, Chancellorsville, the Wilderness, and Spotsylvania Court House—travel west on Route 3, then turn left onto Route 20 (the Constitution Highway). At Orange, turn left onto Route 15. At Gordonsville, enter the roundabout and exit onto VA-231. At Cismont, VA-231 becomes VA-22. This route passes several privately owned historic properties including Castle Hill (built by Dr. Thomas Walker, discoverer of the Cumberland Gap) and Edgehill (home of Thomas Jefferson Randolph, Thomas Jefferson’s favorite grandson). Continue past Keswick, turn left onto Route 250, and turn right at the first light onto North Milton Road. Drive past Clifton (built by Thomas Mann Randolph, Jr., Thomas Jefferson’s son-in-law), cross the Rivanna River, then turn right onto Milton Road (the route used by the Marquis de Lafayette when he visited Jefferson in 1824). Follow Milton Road for 3 miles, then turn left onto Route 53. Drive for ½ mile, past Jefferson Vineyards on the right, then turn right onto State Route 795—the James Monroe Parkway. Continue ½ mile. James Monroe’s Highland is on the right.