Rolling Hills And Charming Inns Are The Calling Cards Of This Quaint Virginia Town

There’s a lot of history behind the town of Orange, Virginia, which celebrated its 150^th birthday in 2022. Nestled in the shadow of the Blue Ridge Mountains, as part of Virginia’s Piedmont region, Orange is a quiet hamlet of around 5,000 folks that’s within easy driving distance of more populated locales like Charlottesville (20 miles), Richmond (60 miles), and Washington, D.C. (70 miles). If you take a trip to this lesser-known destination, expect small town charm from shops and restaurants in its Main Street district, hospitable hosts at local bed and breakfasts, and a lesson in history thanks to the town’s proximity to U.S. president and Founding Father James Madison’s Montpelier. Here are the 10 best things to do in Orange, Virginia.

What To Do In Orange, Virginia

Learn The Town History

There are several spots around town where you can get a glimpse into what Orange was like during its early days. The historic Orange County Courthouse, built in 1859 at the center of downtown, is a good place to start. A short walk away, you can learn all about the town’s history at the James Madison Museum of Orange County Heritage. Finally, stop into the Historic Orange Train Station, which was built in 1909 and now hosts the county’s visitor’s center, to get more general information about the town and its railroad past.

thejamesmadisonmuseum.net; 129 Caroline Street, Orange, VA 22960; 540-672-1776

Visit James Madison’s Montpelier

The big attraction near Orange is the historic plantation and lifelong home of James Madison known as Montpelier. Visitors to the national landmark have an opportunity to not only see the place that one of our Founding Fathers called home, but to learn about his impact—both good and bad—on the country. The site serves as a memorial to both James Madison and enslaved people. It’s also a museum of American history and a place to learn about the Constitution. Exhibits and galleries like “Color Through A Child’s Eyes”, “The Mere Distinction of Colour,” and “Mysteries of Montpelier” aim to tell a more complete story of the historic site and the time in which it was built. Visit the site on the first weekend in November to attend the Montpelier Hunt Races, a steeplechase horse race that's taken place here for almost 90 years.

montpelier.org; 1350 Constitution Highway, Montpelier Station, VA 22957; 540-672-2728

 Get Inspired At The Arts Center

For more than three decades, The Arts Center has been a hub for Orange’s creative community and appreciators of the arts. Visitors can check out two gallery spaces: the storefront Morrin Gallery, which features 6 to 8 curated exhibitions annually, and the Community Gallery, which hosts artist-led projects, residencies, and other community programming. The center also offers regular ceramic studio time, classes, workshops, camps, and more.

artscenterinorange.com; 129 E. Main Street, Orange, VA 22960; 540-672-7311

Go Skydiving

If you want to take a walk—or should we say jump—on the wild side, book a session with Skydive Orange, which has been taking folks high into the sky since 1977. As one of the most established skydiving centers in the country, this is a great place to finally check off that bucket list item. You’ll free fall from a height of 13,500 feet in the air, leaving plenty of time to soak in the surrounding sights of rolling hills, dramatic mountains, and all-around stunning scenery.

skydiveorange.com; 11269 Hangar Road, Orange, VA 22960; 703-SKY-DIVE

Shop Downtown

Strolling and shopping along Orange’s Main Street is the perfect afternoon activity. Restaurants, boutiques, and locally owned specialty stores line the cheery streets, so there’s plenty to pique everyone’s interest. A couple of extra-special spots include Grelen Downtown and Objects on Main. Grelen Downtown is a well-curated gift shop and sister store to The Market at Grelen, a European-style garden shop and café located on a 1,000-acre nursery just down the road from Orange. If you love Grelen’s downtown outpost, take the quick drive to its flagship, where you’ll also find six miles of hiking trails and u-pick fruit in certain seasons. Objects on Main is your go-to shop for eclectic home décor, art, furniture, apparel, and more.

Where To Eat & Drink In Orange, Virginia

Try The Quail Lewis At Spoon & Spindle

Celebrated chef Edna Lewis, who’s often referred to as the Mother of Soul Food or the Grand Dame of Southern Cooking, was born and raised in Orange County. Her style of cooking contributed greatly to the world’s understanding of Southern cuisine. At Spoon & Spindle, Chef Lewis is honored with a dish called Quail Lewis (quail stuffed with wild rice and white grapes). Open for lunch and dinner, as well as brunch on Sunday, Spoon & Spindle offers an elevated Southern fusion menu where dishes like Boudin Spring Rolls, Bourbon Glazed Pork Loin, and Po’Mi (a po’boy-banh mi mashup) all share space on the same menu.

spoonandspindle.com; 323 North Madison Road, Suite H, Orange, VA 2290; 540-360-3004

Enjoy A Farm To Table Dinner At Forked on Main

As a “farm to fork” restaurant, this downtown eatery is committed to creating tantalizing dishes using locally sourced meats, produce, and ingredients whenever possible. The dinner menu offers a little of everything, from Shrimp Scampi Risotto to Grilled Chicken Skewers to Steak & Frites. Come early to catch happy hour (Wednesday through Friday from 4 p.m. to 7 p.m.). For dinner and a show, make a Thursday reservation; there’s live music from 6 p.m. to 9 p.m.

forkedonmain.com; 124 West Main Street Orange, VA 22960; 540-308-7660

Get A Classic Meal At Main Street Tavern

If you’ve got a hankering for a traditional meal, whether that be a hamburger with fries or meatloaf and mashed potatoes, Main Street Tavern is the place to satisfy your cravings. Snag a seat on its charming alley patio, or in the cozy dining room, order a craft cocktail or beer, and get ready to be impressed.

msttavernva.com; 110 E Main St., Orange, VA 22960; 540-661-0004

Grab A Pint And Slice At Iron Pipe Alewerks

The father-son duo behind Iron Pipe Alewerks started their business in their family garage. Over a decade later, they’ve upgraded their operation to a brewpub inside the 1929 American Silk Mill Factory building downtown. Several of Iron Pipe’s brews have won awards, like their OC Light, which won the 2023 gold medal in the U.S. Beer Open, and the Gandalf the Haze, which won bronze in the same competition. Since nothing goes with beer like pizza, Iron Pipe also makes an awesome brick-oven pizza.

ironpipealewerks.com; 323 N Madison Road Orange, VA 22960; 540-522-0673

Where To Stay In Orange, Virginia

Choose a Charming Inn

Hotels and home rentals are both great depending on the vacation vibes you’re hoping to achieve, but in Orange, the undisputed best place to stay is an inn. Though the town is small, its selection of inviting inns is large. The Inn at Willow Grove is the ultimate in elegance and luxury with a 3,000-square-foot spa, full-service restaurant, and spacious suites. For a touch of romance, check into the 1895 restored plantation home known as the Mayhurst Inn. Its rooms feature period décor, Italian marble fireplaces, and whirlpool tubs. The Holladay House’s six guest rooms are situated conveniently in the heart of downtown. For an extra- special experience, make a reservation for high tea complete with porcelain teapots, finger sandwiches, and pretty pastries.