Road Trip Itinerary: Washington D.C. to Culpeper

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Road Trip Itinerary: Washington D.C. to Culpeper


Washington D.C. to Culpeper (Route 29)

Need a break from the bustle of our nation’s capital? From Washington, D.C., Culpeper is the perfect small-town destination with much to see in between. With mountainous and spirited stops along the way, the trip offers a refreshing escape from the hustle and bustle for a slower pace of life.

Drive to Culpeper

Start the day with a visit to District Winery, a boutique winery set in The Yards of D.C. The waterfront views of the Anacostia River can’t be beat, especially while enjoying the fruits of Washington’s first winery. District also offers restaurant and patio dining with small plates and shares.

Before heading west from D.C., make sure to reserve a spot for a walking tour of the Manassas Museum in Old Town Manassas. See the historic sites that contribute to local and national history, including the Industrial School & Jennie Dean Memorial – the original site of the Manassas Industrial School for Colored Youth, founded by former slave Jennie Dean in 1893. Then head over to boutique farm winery Molon Lave Vineyards in Warrenton. Sitting on 50-acres of land surrounded by scenic forests and ponds, the winery specializes in the traditional European wine-making techniques.

Stay in Culpeper

Once in Culpeper, stop at Mountain Run Winery, housed in a historic barn as testament to the farm’s agricultural roots. This winery represents the spirit of community in Culpeper and presents a down-to-earth experience in Virginia’s wine country.

Rest up for the night at Culpeper Center Suites—a cozy, boutique stay with luxurious amenities to make you more comfortable. In the morning, grab a field-to-fork brunch at the art deco styled Flavor on Main before setting off to enjoy other Culpeper offerings nearby.

Drive home from Culpeper

Start your trip back at Old Trade Brewery in Brandy Station, which has a family-friendly environment equipped with indoor and outdoor seating areas and games. Stop at Brandy Station Battlefield for a self-guided tour of the battlegrounds. Brandy Station was the site of the largest cavalry battle in North American history and began the Gettysburg campaign. You can hike the trails and walk where soldiers once did at one of the highest points of the Civil War.

Next, make a pit stop at Vint Hill Craft Winery, housed in a hundred year old barn. The farm was first established before the Revolutionary War, and later became a nest of spies that would eventually become the first location of the NSA. It’s the perfect final adventure before heading home.