∙From I-64 (either coming east from Staunton/Waynesboro or west from Richmond): Take exit 121-A onto Route 20 and after about 1/4 of a mile turn left onto Route 53 at the second traffic light.   Route 53 will wind up the mountain past Michie Tavern and Monticello.  After you pass Jefferson Vineyards on the right, turn right onto State Route 795 (James Monroe PKWY). Continue for 1/2 mile and Ash Lawn-Highland’s driveway will be on the right. 

∙From downtown Charlottesville: From the downtown mall area, turn right onto Route 20-South. Route 20 will turn left and become Monticello Ave.  Continue on Rte. 20/Monticello Ave. until you pass under I-64.  Turn left on Route 53 at the second traffic light and continue up the mountain past Michie Tavern and Monticello.  After you pass Jefferson Vineyards on the right, turn right onto State Route 795 (James Monroe PKWY). Continue for 1/2 mile and Ash Lawn-Highland’s driveway will be on the right. 

∙From Northern Virginia/Culpepper: If coming from Northern Virginia via I-66, take exit 43A and continue on Hwy 29 South.  When you get close to Charlottesville, follow signs for the Hwy 29/250 West Bypass which will take you around the city of Charlottesville. Once you reach the Bypass, follow signs directing you to I-64.  Take I-64 East toward Richmond to Exit 121A, Route 20.  After about 1/4 mile turn left onto Route 53.  Route 53 will wind up the mountain past Michie Tavern and Monticello.  After you pass Jefferson Vineyards on the right, turn right onto State Route 795 (James Monroe PKWY). Continue for 1/2 mile and Ash Lawn-Highland’s driveway will be on the right. 

∙From Fredericksburg/I-95: If coming from Northern Virginia, exit I-95 at Fredericksburg (Route 3). Continue on Route 3 until you reach Route 20 (Constitution Highway) on your left. Continue on the Route 20 until you reach the town of Orange. Once you reach Orange, turn left onto Route 15.  After driving 8 miles, enter the next roundabout and take 2nd exit onto VA-231.  VA-231 becomes Rte. 22 (Louisa Rd). Continue through Keswick until you reach Hwy 250. Take a left on Hwy 250 (Richmond Rd), then a right onto N. Milton Rd., then another right on Milton Road. After following Milton Road for about 3 miles, the road will intersect Route 53. Take a left on 53, drive for 1/2 mile past Jefferson Vineyards on the right, then turn right on Route 795 (James Monroe PKWY). The Ash Lawn-Highland drive is located 1/2 mile on the right.

∙From Lynchburg: Take Hwy 29 north to I-64.  Take I-64 East toward Richmond take Exit 121. You will exit the interstate onto Route 20 South.  After about 1/4 mile turn left at the second traffic light onto Route 53.  Route 53 will wind up the mountain past Michie Tavern and Monticello. After you pass Jefferson Vineyards, turn right onto State Route 795 (James Monroe PKWY).  Continue for 1/2  mile and Ash Lawn-Highland’s driveway will be on the right. 

∙From Fluvanna/Palmyra: Take Route 53 toward Charlottesville, turn left on Route 795 (James Monroe Parkway). Continue on 795 for 1/2 mile. Ash Lawn-Highland driveway is on right.

∙Journey Through Hallowed Ground Route: (a scenic drive following Routes 15 and 20) Coming from the Fredericksburg, Chancellorsville Battlefield, or the Wilderness Battlefield.  Take Route 15 (The Constitution Highway) until you reach the town of Orange, Virginia. Once you reach Orange, turn onto Route 20 South.  After driving 8 miles, enter next roundabout and take 2nd exit onto VA-231 South. VA-231 becomes Rte. 22 (Louisa Rd). This route will take you past several historic and privately owned properties including Castle Hill, Edge Hill, and Clifton.  Continue through Keswick until you reach Hwy 250. Take a left on Hwy 250 (Richmond Rd), then a right onto N. Milton Rd., then another right on Milton Road. After following Milton Road for about 3 miles, the road will intersect Route 53. Take a left on 53, drive for 1/2 mile, then turn right on Route 795 (James Monroe PKWY). The Ash Lawn-Highland drive is located 1/2 mile down Route 795 on the right.