Orange County, Virginia Road Trip

James Madison, Orange VA
President James Madison’s home near Orange, VA. Photo by Kurt Jacobson

By Kurt Jacobson
GoNOMAD Senior Writer

If you’ve heard about Orange County, Virginia, it was most likely because it’s the former home of America’s fourth president, James Madison. While visiting Madison’s home, Montpelier is a must; Orange County has much to offer prospective visitors.

I had heard of the town of Orange from my friend John, who visited us in Colorado back in 2008. We hosted him to help with hiking and mountain climbing. Although he told us about Orange, VA, it meant almost nothing then. Who knew we’d move from gorgeous Evergreen, Colorado to Baltimore in 2008?

In 2010, we visited John at his home in Orange and it still didn’t register what an amazing place Orange County is. Then in 2016 I stayed at The Inn at Willow Grove, a historic 1770s restored home. While staying at the Inn on the outskirts of Orange, I got to know the area better.

It’s about a four-hour drive to Orange County from my home north of Baltimore, and well worth the drive for excellent wine, dining, historic sites, hiking, and first-class lodging.

Downtown Culpeper's main drag has several historic buildings. Photo by Kurt Jacobson
Downtown Culpeper’s main drag has several historic buildings. Photo by Kurt Jacobson

Culpeper and Beyond

By the time I hit Culpepper, a great place to explore in its own right, the big cities were far behind me. The road was now a slideshow of farms, forests, and historical sites like The Battle of Cedar Mountain. I stopped at the historical marker at the border of Orange County and learned that the county was formed from Spotsylvania County in 1734.

My next stop was at the visitor’s center in downtown Orange where I met Rich who was the lone occupant of the office.

The old train station is an appropriate place to house the visitor’s center and a great place to start your exploration of Orange County.

The building has clean restrooms and is an excellent place to park then walk around downtown. Be sure and get a copy of A Walking Tour of the Downtown Orange Commercial Historic District at the visitor’s center.

Virginia Road Trip to Barboursville

orange county va map
I didn’t linger in Orange as I’d return the next day to continue exploring. I had lunch reservations at one of the best wineries east of the Mississippi River nearby and I was hungry. Palladio is the onsite restaurant of Barboursville Winery in the tiny town of… you guessed it, Barboursville.

This was my fourth time dining at Palladio in the last six years, and I looked forward to the meal. Michael Clough was an intern in 2013 and worked his way up to Executive Chef in 2020. Michael was sent to Italy by Barboursville Vineyards to further his education in Northern Italian cuisine.

I can vouch for his talents as I had the roasted squab with a side of grilled asparagus and mashed new potatoes on that day. The meal was fabulous and made even better by the complimentary bread, olives, and half glass of Prosecco.

After lunch I took a walk in the three-acre Allegrante meadow that head winemaker Luca Paschina has planted to support nature and pollinators. The name Allegrante is from a racing horse Governor Barbour owned that went on to win three Kentucky Derby races in the 1800s. With all sorts of birds and pollinators buzzing about I enjoyed this natural space and its beauty.

Barboursville winery is just behind the Allegrante Meadow. Photo by Kurt Jacobson
Barboursville winery is just behind the Allegrante Meadow. Photo by Kurt Jacobson

A Hidden Market

After my walk in the Allegrante meadow I headed to a little known nursery/restaurant called The Market At Grelen. The market is on a 1,000 acre tree farm that opened for special events, market, restaurant, nursery plants, and pick-your-own fruit.

The day I arrived they had gorgeous Gloria peaches for u-pick or just cash and carry. I asked the general manager Stacie how customers find you and she said, “We don’t do any advertising, so the majority of people find us through word of mouth.”

I also asked Stacie what her favorite comments were from first-time visitors that found Grelen and she told me, “We have heard first-time visitors say on several occasions: “This seems like the kind of place you would fall in love.”

Grelen is a magical place, and you can typically spot a “first-timer” by the look of awe and amazement on their face.” I find the Market at Grelen to be a happy place with numerous areas to linger and enjoy with a glass of wine and lunch from their café.

The Market at Grelen's cafe is a hidden treat for food and local beverages. Photo by Kurt Jacobson
The Market at Grelen’s cafe is a hidden treat for food and local beverages. Photo by Kurt Jacobson

The café has comfortable and shady outdoor seating available and welcomes day visitors.

The menu includes sandwiches, a couple of salads, a grain bowl, snacks and appetizers. For beverages they have local wines, cider, and beer highlighting just how good Orange County and other VA adult beverages are. On my way out I noted that there are hiking trails I’d end up coming back to try later.

Back to the Inn

The 1804 Inn was my lodging for the night. The Inn is located next to the Historic Barboursville Ruins, once the home of the famous former governor, commander of Virginia’s militia during the War of 1812, senator, and U.S. Secretary of War. James Barbour was also a close friend of Thomas Jefferson, who designed the house that was destroyed by fire on December, 25, 1884.

The Barboursville Ruins are a bit spooky. Photo by Kurt Jacobson
The Barboursville Ruins are a bit spooky. Photo by Kurt Jacobson

The ruins are open to the public and quite a sight. If you visit Barboursville Winery’s tasting room or stop in for lunch, be sure and take the short walk to the ruins

Wine flight at Barboursville Vineyards.
A wine flight at Barboursville Vineyards. Photo by Kurt Jacobson

After using the convenient self-check-in, I deposited my bags in the Octagon Room and headed to the tasting room at the main winery complex up the hill. I chose a flight of three white wines and loved the new white blend called Nascent. I was pleasantly surprised when Luca stopped by to chat with me.

Luca had been in Italy for a vacation and shared photos of mushroom foraging in Italy. We also talked about our shared love of vegetable gardening and when I asked Luca if I could see his garden, he invited me to his home for a garden tour.

After a short tour he asked me if I had dinner plans, and since I didn’t, he said, “Why don’t you come back to the house for dinner around 7 or 8, and we’ll have a simple garden salad, pasta, and some wine.” That was an offer I couldn’t refuse.

Dinner was a delicious salad of tomatoes, cucumbers, jalapeno peppers, and a homemade dressing. His pasta dish was linguini with tomatoes, olives, and special capers he brought back from Italy. Paired with Barboursville Fiano, it was an exceptional meal spent talking about fishing; we both love fishing, food, wine, and local history.

On the Road Again

After a delicious breakfast of sautéed apples from the tree nearby, an omelet, bacon, yogurt parfait, and a croissant, I headed to Gordonsville.

Highlights of Gordonsville are the Exchange Hotel—said to be in the top 20 most haunted places in the US—The BBQ Exchange, the Icehouse restaurant for fried chicken, and the historic downtown area.

Gordonsville Orange County
The Exchange Hotel in Gordonsville is said to be haunted. Photo by Kurt Jacobson

On a recent Virginia road trip, I discovered the Jackson Market offering baked goods, a coffee bar, chilled wine, grab-and-go foods, and specialty grocery items.

The Jackson Market gets its baked goods from Albemarle Baking Company and MarieBette Bakery, both in Charlottesville and both fantastic bakeries.

I bought specialty beans, fettuccine, and a cookie bar before returning to Grelen for a hike.

Jackson & Company Market Gordonsville. Photo by Kurt Jacobson
Jackson & Company Market Gordonsville.

For lodging in Gordonsville, I recommend the Nathaniel Inn, a historic home on Main Street that operates as an Airbnb. I love that the Inn is walking distance to most everything on the main drag and is dog-friendly.

Take a Hike

The Market at Grelen has 6.5 miles of easy to moderate grassy trails through the trees. I met joggers, a dog walker, and some tree workers on my hike. I asked the dog walker if he came there often, and he said,” I come here almost every week to get in a good hike for me and my black Lab.”

The Blue Ridge Mountains were just visible the day I hiked the trails at Grelen. Photo by Kurt Jacobson
The Blue Ridge Mountains were just visible the day I hiked the trails at Grelen. Photo by Kurt Jacobson

I enjoyed the view of the farm from the Grelen Overlook and fast-walked the approximately two-mile hike in 40 minutes.

Back at the market I saw a mother with three kids and a large box of fresh-picked peaches and big grins.

Unfortunately, I didn’t have time to pick fruit as I was having lunch with my friend John at MST-Main Street Tavern in Orange

Since I arrived too early for lunch, I stopped at the James Madison Museum. Bethany, the lady working that day, was a wealth of information.

I learned that Orange County was once the largest counties in the US. So large was Orange County; it encompassed modern-day states of WI, MI, IL, KY, OH, IN, and WV. Obviously, it’s not that large these days but it’s still a grand county.

The James Madison Museum in Orange is a good source for local history. Photo by Kurt Jacobson
The James Madison Museum in Orange is a good source for local history.

Bethany also showed me highlights like the oldest home in Orange County, a bust of James Madison, and impressive hand-carved truck toys that looked like the real thing from the 1950s. If you visit, ask her who carved them and how old he was when the toys were created.

Lunch With an Orange County Local

A white tailed deer in Shenandoah National Park. Photo by John Harpine
A white tailed deer in Shenandoah National Park. Photo by John Harpine

I enjoyed hearing about Orange and what there was to do in the area from my friend John as we ate lunch. Besides golfing, one of John’s favorite things to do is driving up to Shenandoah National Park and looking for wildlife. Shenandoah is only about a 40-minute drive from Orange

John showed me photos of a black bear, a deer, and a rattlesnake he’d seen on his visits to Shenandoah. With miles of trails in the park, who knows what you might see if you go there?

An Amazing Maze

On a follow up trip to Charlottesville and Orange County I visited Liberty Mills Farm. I met farmer Kent Woods, the mastermind behind the most amazing corn maze I’ve ever seen.

Kent used to be an engineer and it shows when you look at his past corn maze creations. The Farm maze is open weekends in September until mid-November.

On that follow up Virginia road trip I had the pleasure of staying at The Inn at Willow Grove again.

This historic Inn offers a wide range of lodging options like luxury cottages, rooms at the Inn, and boutique rooms in two creekside cottages with six rooms in each. Their restaurant Vintage serves breakfast, dinner, and Sunday brunch.

2023 Liberty Mills Official Photo
The 2023 corn maze at Liberty Mills Farm was a work of art. Photo by Liberty Mills Farm

The Millhouse Spa and pool were added since my last visit, and delivered one of the best couples massages my wife and I have ever had. The couples massage room has a separate relaxation area with lounge chairs so comfortable and the music so calming, we had to practically pry ourselves out of a dream state to receive our frangipani hot stone massage treatments.

The Inn at Willow Grove's Millhouse Spa. Photo by Kurt Jacobson
The Inn at Willow Grove’s Millhouse Spa. Photo by Kurt Jacobson

If You Go to Orange County

I suggest visiting in spring, early summer, and fall. Orange County is an excellent place for a Virginia road trip, and you can find helpful information at to find lodging, restaurant, attractions, and more.

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