The Best Fall Foliage Drives from Annapolis

Maryland’s fall foliage is one of the best-kept secrets in the Mid-Atlantic. While the Catskills and the Berkshires draw the crowds, the rolling hills of Western Maryland and the river valleys of the Eastern Shore quietly put on a display that, in peak weeks, is as good as anything in New England. From Annapolis, three drives each offer something distinct.

The shortest and sweetest is the drive north along the Chesapeake Shore from Annapolis toward Chestertown. Take Route 301 north to Kent County, where the farm roads between Chester River tributaries canopy over with oak, sweetgum, and black tupelo in shades of deep scarlet and burgundy. Stop at the Chestertown Saturday market if you time it right; the local apple ciders and quince pastes are exceptional in October.

The second drive takes you west toward Western Maryland wine country, through Howard and Frederick counties. Route 97 into Montgomery County is unremarkable but Route 650 north out of Damascus into Laytonsville begins the serious foliage. The Sugarloaf Mountain trail network, accessible from the parking area off Comus Road, is 30 minutes of the best forest walking within two hours of Annapolis. Peak color here typically runs the second and third weeks of October.

The longest but most spectacular option is the drive to the western mountains: Interstate 70 west to Hagerstown and then south on Route 40 through Washington County toward the Antietam National Battlefield and the South Mountain ridges above Boonsboro. The maple-beech ridgeline above Boonsboro turns orange and yellow in early October with a consistency that makes it the closest thing Maryland has to a guarantee.

All three drives can be made as day trips from The Alderton, with a 7 am breakfast at The Compass Rose and a return in time for dinner. Our concierge keeps a foliage tracking map updated weekly in October and can advise on the current peak conditions for each route. We can also arrange private car service for any of the drives—a particularly good option for the Western Maryland run, which benefits from a driver who knows the back roads.