The Best of Virginia and Maryland in 12 Days

View of shops along the waterfront with the state's capitol building visible in the distance.

Waterfront in downtown Annapolis, MD. Photo © Steven Frame/123rf.

Virginia and Maryland encompass a large amount of land. It can take six hours to drive from Washington DC to the southern end of Virginia and nearly four hours to drive from western Maryland to the Eastern Shore. A 12-day trip provides the opportunity to hit most of the highlights of the region and get a good feel for both states.

Washington DC makes a good starting point for exploration of Virginia and Maryland. It is centrally located and convenient for air, train, bus, and car travel. Spend a couple of days at the beginning of your trip exploring this marvelous city.

Map of Frederick and Western Maryland

Frederick and Western Maryland

Frederick and Western Maryland

Day 1

From Washington DC, drive three hours northwest to the far reaches of Maryland to enjoy the mountain air at Deep Creek Lake. On your way, stop in Frederick for lunch in the historic downtown area. Overnight at the Carmel Cove Inn at Deep Creek Lake.

Day 2

Spend the day at Deep Creek Lake State Park, enjoying the outdoors. Swim, fish, or canoe on the beautiful lake or take a hike on one of the many trails on Meadow Mountain. Spend the night in another local inn or pitch a tent at the Meadow Mountain Campground.

Shenandoah and Northwestern Virginia

Day 3

Drive 2.25 hours southeast into Virginia and have lunch in charming Winchester. Spend a little time touring this lovely town and visit the Museum of the Shenandoah Valley before continuing 30 minutes south to Front Royal, the gateway to Shenandoah National Park.

Visit a stunning subterranean world at Skyline Caverns, then spend the night in Front Royal.

Day 4

Make this day all about Shenandoah National Park. Drive Skyline Drive and stop along the way to take in breathtaking vistas or to do a short hike. End your day by driving to Lexington and spending the night in this historic town.

Map of Central and Southern Virginia

Central and Southern Virginia

Central Virginia

Day 5

Spend the morning in Lexington seeing the sights. Take a carriage tour or visit the Virginia Military Institute and the Stonewall Jackson House. Then make the scenic one-hour drive east to Charlottesville and visit a vineyard before treating yourself to a night at either the Clifton Inn or Boar’s Head Inn.

Day 6

Visit Thomas Jefferson’s Monticello in the morning and then have lunch on the hip downtown mall in Charlottesville. After lunch, drive southeast about an hour to the state capital of Richmond. Orient yourself in this busy city and if time allows, take in the Science Museum of Virginia. Overnight in Richmond. For a splurge, spend the night in the historic Jefferson Hotel.

Coastal Virginia

Day 7

Visit Capitol Square in Richmond before heading southeast for a one-hour drive to Colonial Williamsburg. Dine in Merchants Square and spend the night in one of several hotels run by the Colonial Williamsburg Foundation.

Day 8

Lose yourself in U.S. history by dedicating the day to exploring Colonial Williamsburg. Visit the museums, shop in the authentic colonial shops, talk to the costumed interpreters, and drink and dine in the local taverns. Spend another night in Williamsburg.

Day 9

Make the 1.25-hour drive to Virginia Beach early so you can enjoy a day on the Atlantic.

Visit the Virginia Aquarium & Marine Science Center and walk the famous boardwalk. Enjoy fresh seafood at one of the local restaurants and spend the night in a hotel right on the ocean.

Map of Maryland's Eastern Shore and Atlantic Beaches

Maryland’s Eastern Shore and Atlantic Beaches

Maryland’s Eastern Shore and Atlantic Beaches

Day 10

Drive northeast three hours through the famous Chesapeake Bay Bridge-Tunnel and continue up the scenic Eastern Shore to Ocean City. Soak in the activity on the busy boardwalk and be sure to eat some Thrasher’s French Fries. Spend the rest of your day at the beach.

Day 11

Drive two hours northwest to the charming Eastern Shore town of St. Michaels. The sharp contrast to Ocean City will be readily noticeable as you stroll through the historic downtown area full of restaurants and boutiques or perhaps take a cruise from the waterfront. Spend the night in St. Michaels in one of the waterfront inns.

Annapolis

Day 12

On your last day, drive about an hour northwest over the Chesapeake Bay Bridge to Maryland’s capital city, Annapolis. This beautiful and historic waterfront city on the Chesapeake Bay is the perfect place to end your trip. Visit the Annapolis City Dock, the U.S. Naval Academy, and the Maryland State House. Be sure to dine on local blue crabs if you’re a seafood lover.


Excerpted from the First Edition of Moon Virginia & Maryland.

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