Orange County Virginia: History, Shopping,Vineyards

Orange County (and the surrounding area) is known as the “Cradle of Democracy” because four United States Presidents – Jefferson, Madison, Monroe and Taylor – were either born or built their private estates along this historic ninety-mile route. For your next road trip, consider a drive through Virginia countryside to see some of these important landmarks.

My favorite has to be Montpelier. During a visit to this historic mansion and gardens, it is easy to immerse yourself in 18th century American culture through the guided tours and the period furnishings representing the time when the Madison’s lived there.

The gardens around James Madison’s Montpelier are serenely beautiful.

 James and Dolley Madison played a pivotal role in America’s earliest history. The couple entertained their fellow founders of the United States at Montpelier Estate, including Virginian’s George Washington and Thomas Jefferson, as well as Alexander Hamilton and the Marquis de Lafayette. The Estate operated like a “Think Tank” where principles of the nation’s founding documents were discussed and strategized. Montpelier is lesser known than Jefferson’s Monticello, but equally inspiring. 

Montpelier Estate is where James and first lady Dolley Madison lived.

Your first stop should be Montpelier’s Visitors Center. An introductory film is followed by a walking tour of the Mansion and grounds with local historians. They explain how archeologists uncovered artifacts, including excavating the buried slave quarters. On certain Saturdays living history actors are on the grounds and available for conversation. Montpelier is surrounded by 2,650 acres of horse pastures and gardens. You can also visit the Gilmore House, a restored cabin that was home to a freed African American family after emancipation.

This dynamic duo developed some of the abiding principles of our most enduring documents including the US Constitution

First Lady Dolley Madison was the consummate American hostess and diplomat. She regularly entertained and is quoted in a letter to her sister: “Tonight we hosted 100 people for dinner, but fortunately, only 25 stayed the night.” I could imagine these souls inhabiting the home and acres of gardens as I explored. There’s a graveyard where the Madison’s are buried and a separate burial site for the enslaved people who lived at Montpelier.

Vineyards and farmer’s markets are a few miles from Montpelier Estate, so, you can enjoy the countryside and learn at the same time! Don’t miss the Market at Grelen, a farm featuring the harvest from their fruit orchards, a nursery and garden center. The small cafe serves vegan quiche and fig jam and toast. Grelen events like Picker’s Paradise (reclaimed craft and furniture fair), Octoberfest, and glamping for visitors attending the Hunt Races at Montpelier are legendary!

The Market at Grelen Farm has some fabulous finds!

Central Virginia also has a concentrated collection of vineyards and wineries, including Barboursville Vineyards, which allows guests to sample 21 different wines.

Barboursville Vineyard is a marvelous place to sample Virginia wines.

Stay at the 1804 Inn at the Barboursville Vineyards, and feel like a great American hero yourself. This estate was designed by Thomas Jefferson and is known for its octagonal shaped great room – a design seen on the bottles produced at the vineyard. The family was one of the richest in the area, and James Barbour served as Governor of Virginia. In the fall, there are weekly festivals, tastings and harvest time.

wine tasting room at Barboursville Vineyard

Another stupendous reason to visit Orange County is to check out the charming town of Gordonsville. If you are a shopper and or love Civil War history, you’re going to enjoy Gordonsville’s Main Street. Here you can find a number of exquisite high end boutiques, art galleries and antique shops. You can also stop in the Exchange Hotel and Civil War Medical Museum which has been part of the trajectory of American history from pre-Civil War days when it was a hotel. During the Civil War it served as a military hospital, and many soldiers died while being treated here. Hence, the Exchange is considered quite haunted by experts in the paranormal field. After the war, the Exchange Hotel  became the Freedman’s School for Colored Children and a place to adjudicate complaints submitted by the local African American population who dealt with consistent discrimination during Reconstruction and beyond.

During your visit, stop for some authentic hickory smoked meats at the BBQ Exchange in Gordonsville. They have so many delightful sauces to sample with your pork, chicken or even TOFU barbecue. The proteins are smoked in a hickory and charcoal smoker out back. This place is always busy, but it’s worth the wait. Don’t miss the hushpuppies, they are the crispiest, most flavorful I’ve had. The region is a scenic two hour drive from Washington DC. If you go, I would love to hear about your experiences! Write me here or at

family travel History Hotels Kid Friendly Luxury Resorts MidAtlantic Travel Road Trips Travel Vineyards Virginia Travel

Travel and Dish View All →

Freelance writer and photographer specializing in vivid, deeply reported stories about food, travel and family.

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