The Best Things To Do In Orange, Virginia

History, adventure, and relaxation await in Orange, Virginia.

In Orange, Virginia, amber hills of grain melt into purple vineyard vines. It’s where horse farms neighbor tiny villages, and fried chicken is as likely to be on the menu as a crab cake. It’s where people like James Madison made his family homestead and developed his ideals and conflicting principles of freedom, and the Grand Dame of Southern cooking, Edna Lewis, was raised. The history runs deep, the food is soulful, and the people are hospitable.

Three small towns comprise Orange, Virginia. There’s Barboursville, a quaint village marked by impeccable, Italian wines and horse farms. There’s Orange, the county center with tree-lined streets, and all the comforts of home, and then there’s Gordonsville which might as well be Virginia’s own Stars Hollow. 

Relax Amid Pastoral Views

If there is one thing Orange, Virginia knows to do, it’s how to put on a picturesque show. No matter the season, the scenic area shines, especially at the Inn at Willow Grove. The beautifully renovated and well-appointed 1770s historic home offers 25 accommodations ranging from boutique rooms to spacious cottages. French press coffee and piping hot beignets doused in powdered sugar are delivered to your room each morning. During the day, guests can stroll the 40-acre property filled with manicured gardens and trees dating to the Marquis de LaFayette’s campaign in the area, or book a treatment at the Mill House Spa. The onsite eatery, Vintage Restaurant and Pub, offers two distinct menus, one casual and one refined, in side-by-side garden-level spaces.

Savor The Edna Lewis Menu Trail

Renowned Southern chef and cookbook author Edna Lewis spent the first 16 years of her life in Freetown in Orange, County. Lewis is often credited with single-handedly putting African American Southern cooking on the culinary map. As such, regional chefs from Orange and beyond are often inspired by Lewis’s work. In fact, Orange has its own Edna Lewis Menu Trail, a collaboration between seven restaurants to pay homage to some of Lewis’s most storied recipes. Restaurants along the trail include Barbeque Exchange, Champion Ice House, Clearwater Grill, Coopers Cookin and Catering, The Market at Grelen, Spoon and Spindle, and Vintage Restaurant. Beyond the menu trail, visitors to the area can stop at other historical Edna Lewis sites such as Bethel Baptist Church, the James Madison Museum of Orange County Heritage, and the Edna Lewis Historical Marker (coming in early 2023) located in Freetown, her childhood home.

Sip Virginia Wine

There are more than 300 vineyards in the Commonwealth of Virginia, and eight of them sit in Orange County. At Horton Vineyards, you can enjoy over 40 different wines from their 67-acre estate with varietals coming from France Portugal, and Spain. The vineyard is also credited with introducing Viognier to the state as well as reviving the native grape varietal, the Norton. At nearby Barboursville Vineyards, senior winemaker Luca Paschina oversees 176 acres, a tasting room, a second tasting room, Library 1821, an onsite restaurant, Palladio, onsite accommodations, and more, all while getting his hands on the grapes, too. Barboursville specializes in making wines in the Italian tradition. Barboursville Vineyards is best known for its award-winning Bordeaux blend, Octagon, and be sure to try the Paxxito, too, a deliciously nutty dessert wine. For even more wineries such as acclaimed Pippin Hill Farm, dip over to Charlottesville which is just a short drive from Orange.

Reflect At James Madison’s Montpelier

The history at James Madison’s Montpelier is rife with tragedy and triumph. Madison was the fourth President, the Father of the U.S. Constitution, and the drafter of the Bill of Rights. Visitors to Montpelier are offered ticketed tours of the grounds and home where he and his wife, Dolley, once lived and entertained some of the most interesting intellectuals of the time. Tours take a complete approach to history, demonstrating how the rise of the Madisons’ prosperity and prominence was directly related to the more than 300 enslaved people who worked on their land and in their home. “We can’t understand Madison, we can’t understand Montpelier, and we can’t understand the U.S. Constitution without understanding the history of slavery here,” says director of education and visitor engagement Kyle Stetz. "The Mere Distinction of Colour" exhibit in the House Cellars and South Yard examines Montpelier’s enslaved community and slavery throughout the founding era through the lens of the U.S. Constitution, Madison’s most well-known accomplishment. Expect a riveting yet emotional interactive experience

Shop Like A Local

When traveling, one must pick up a souvenir or two. To remember your time in Orange, head to The Market at Grelen. Situated on a 1,000-acre tree nursery the market is best described as a European garden shop and cafe, but it’s truly so much more. There are pick-your-own fruit and vegetable weekends throughout the year based on a ripening schedule found on Grelen’s website. There are 5-miles of hiking trails, some of which lead directly to the grounds of Montpelier. There is homemade ice cream made with Grelen-grown fruits and herbs, and a market shop filled with gardening and home needs. According to co-owner, Leslie Gregg, come Christmas, the market turns into a winter wonderland. When the nursery closes for January and February, The Market offers tastings from their highly curated list of Virginia beer, wine, and cider.

To get your fill of boutique shopping, Gordonsville is your must-stop. The Laurie Holladay Shop is owned and operated by the namesake herself. Holladay comes from a family of small business owners (her dad was a retailer for 75 years!), and after moving to Gordonsville, she wanted to bring the charm of intimate, neighborly shopping to her new home. Her shop offers home decor, women’s accessories, lamp repair, antiques, gifts, and more. It’s truly a delightful treasure trove!

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