Plan Your 15-Day Capital Region Road Trip

Days 1 and 2: Washington, DC

At once an international crossroads and America’s ultimate hometown, Washington, DC offers visitors inspiring museums and monuments, diverse neighbourhoods, world-class restaurants, gorgeous parks and gardens, and endless entertainment and nightlife.

Where else in the world can you visit with a 19-foot President Lincoln (Lincoln Memorial), read the original U.S. Constitution (The National Archives), see Dorothy’s ruby-red slippers (National Museum of American History) and soak in internationally acclaimed art (a number of galleries and museums)? Only here. Get your Capital Region holiday off to a roaring start in Washington, DC.

Days 3 and 4: DC to Baltimore, Maryland

After making the hour-long drive from DC to Baltimore, head for the Inner Harbor, where the Top of the World observation level at the World Trade Center offers a panoramic view of the entire city. Make tracks to the B&O Railroad Museum, where you can hop aboard a historical train, or get a glimpse into the lives of a variety of sharks, marine mammals, reptiles, fish and more at the National Aquarium.

Tempt your taste buds at bars and restaurants in the historic waterfront neighbourhood of Fells Point. In the evening, enjoy the Inner Harbor’s relaxed atmosphere, enlivened by musicians and street performers.

A must-see is Fort McHenry, a star-shaped fort where Americans resisted a British fleet during the War of 1812. Those soldiers’ defence provided the inspiration for America’s national anthem, “The Star-Spangled Banner.”

Day 5: Baltimore to Shenandoah Valley, Virginia

Follow the Historic National Road out of Baltimore and west to Frederick, a crossroads of American history with a small-town feel. Take a walking tour and learn about battlefield surgery in the National Museum of Civil War Medicine before heading south for Antietam, scene of the bloodiest single day in American military history. 

In your next stop, Winchester, Virginia, visit the Museum of the Shenandoah Valley. It tells the story of the valley’s history and the area’s culture, and is surrounded by seven acres of spectacular gardens.

From there, check out the stalactites and stalagmites of Luray Caverns, then drive the breathtaking Skyline Drive through the 200,000-acre Shenandoah National Park. Hike along trails and admire waterfalls, wildflowers and more from one of the 75 overlooks, or take a guided ranger tour or horseback ride through the park.

Heading south, Skyline Drive becomes the Blue Ridge Parkway, “America’s favourite drive.” Continue along the parkway to Roanoke, Virginia, where you will discover a wealth of outdoor recreation right in the heart of the Blue Ridge Mountains.

Day 6: Roanoke to Charlottesville, Virginia

Charlottesville is a college town with a youthful, sophisticated vibe. The surrounding area is famous for wineries, but you can opt for the Red, White and Brew Trail with stops at wineries, breweries, a cidery and distillery in the Blue Ridge foothills.

Not to be missed is Monticello, the only home in the US on the United Nation’s World Heritage list. Thomas Jefferson’s restored mountaintop estate encompasses the house, flower and vegetable gardens, and a plantation that tells the story of a large and diverse community. The visitors centre offers four museum exhibits.

Day 7: Charlottesville to Richmond, Virginia

En route to Williamsburg, tour the historic Richmond area. Step into the state Capitol building designed by Thomas Jefferson, cruise the downtown canal built by George Washington, or check out more than a dozen themed gardens at the Lewis Ginter Botanical Garden.

Days 8 and 9: Williamsburg, Virginia, and America’s Historic Triangle

Experience the beginning, middle and end of Colonial America in a single day via Jamestown, Williamsburg and Yorktown. All three connect via the 23-mile Colonial Parkway.

Jamestown, the first permanent English settlement in the New World, dates back to 1607. In Williamsburg, visitors can explore more than 40 shops and restaurants in Merchants Square and experience Colonial Williamsburg’s Revolutionary City, historic trades, shops and taverns. British colonial rule ended in America at Yorktown on 19 October 1781, when Lord Cornwallis surrendered to George Washington’s besieging army.

Voted the world’s Most Beautiful Park year after year, Busch Gardens Williamsburg will set your adrenaline racing with 100 thrilling rides and attractions. At Water Country USA, Virginia’s largest water park, enjoy water slides and rides — it’s a day of fun for the whole family.

Days 10 and 11: Virginia Beach

Drive southeast from Williamsburg to Virginia Beach, which holds a Guinness World Record as “the world’s longest stretch of pleasure beach.” Stroll the 40 blocks of boardwalk, and be sure to stay until the sun drops; that’s when the waterfront comes alive.

The next morning, hike through First Landing State Park, the most visited state park in Virginia. Walk through salt marsh habitat, freshwater ponds, beach, dunes, tidal marsh and cypress swamp.

Days 12 and 13: Chesapeake Bay and Maryland’s Eastern Shore

Drive north and cross the Chesapeake Bay Bridge-Tunnel. See the world’s largest collection of decorative and antique decoys at the Ward Museum of Wildfowl Art in Salisbury. In the port town of Cambridge, visit the Blackwater National Wildlife Refuge, an important nesting and feeding area for bald eagles, ospreys and waterfowl.

St. Michaels was dubbed “the town that fooled the British” when locals hung lanterns in the trees, tricking the Royal Navy into overshooting the houses, during the War of 1812. Today it’s a romantic spot for strolling its historic streets and popping into boutiques or feasting on crab cakes while overlooking the harbour. Easton is a top-10 honouree in the book 100 Best Small Towns in America. Tiny Oxford, featured in James Michener’s novel Chesapeake, is reached by the longest cable-free ferry in the USA.

Day 14: Annapolis, Sailing Capital of the USA

Leave Maryland’s Eastern Shore via the soaring Chesapeake Bay Bridge for Annapolis, with its host of Colonial buildings clustered around the 18th-century Maryland State House, the oldest State House in continuous legislative use in the nation. Enjoy lively cafes and bars along the waterfront, or browse the shops along the brick-lined streets of the Annapolis Historic District. Take a scenic harbour cruise and a guided tour of theUS Naval Academy.

Day 15: Back to DC or Baltimore

Take a last lingering look at the scenery of the Capital Region USA en route to Washington, DC or Baltimore to drop off your car and catch your flight home.

Find more itineraries for exploring in the Capital Region and check out our latest Holiday Guide online.