Your first stop should be Belle Grove Plantation in Middletown, birthplace of James Madison. If you’re coming from the Southeast, you’ll want to start your morning with a stop at Happy Creek Coffee and Tea in Front Royal, nested in Warren County.
Twenty-five miles up the road, you’ll arrive at Belle Grove Plantation Manor House. The home was built in 1797 and sat at the center of what eventually became a 7,500 acre plantation, growing cattle, wheat, and sheep sustained by hundreds of enslaved people.
The Plantation offers guided house and grounds tours featuring the Manor House, ice and smokehouses, apple orchard, and slave cemetery. The visitors’ center also offers a self-guided tour of the plantation so that you can explore and take in the history of both the main house and that life of those who were enslaved on the property.
To give yourself more time to explore, consider packing a picnic lunch.
After an afternoon of learning and conversation, head to nearby Winchester’s pedestrian mall for a wide selection of local eats. Once you’ve had your fill at local hot spots, like Water Street Kitchen or Broken Window Brewing, plan to stay in Berryville at the beautiful Historic Rosemont Manor. You’ll be a short distance to wake up and tour the Josephine School Museum, next up on the list.