Historic Inns of Virginia: A Taste of History

Written by Kurt Jacobson

October 13, 2023
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The best way to experience Virginia’s countryside hospitality is to take a road trip to one of these inns. Read on for our favorite historic inns of Virginia.

The fact that there are many historic inns in Virginia is partly due to the long history of this great state. I’ve been exploring Virginia since 2008 and have just begun to find the treasures it offers. Not only is there a rich history from the Revolutionary War, the War of 1812, and the Civil War, but there’s also plenty of African-American history.

I’ve been fortunate to see many of Virginia’s small towns over the years and noted just how many historic inns still survive. Let’s take a road trip and explore some of these towns and inns that still beckon weary travelers to rest, eat a meal, and perhaps enjoy a pint.

Keswick Hall

The first historic inn I came to know was Keswick Hall on the outskirts of Charlottesville. Though the youngest of the Inns covered here, it has a lot going for it. Like many establishments I visited, Keswick Hall is close to Washington, DC. Initially built in 1912, Keswick Hall recently staged a massive four-year renovation of the property, and looks better than new.

Keswick Hall view from the front side. Photo by Kurt Jacobson

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With 80 guestrooms and suites, you’re sure to find a perfect fit. For recreation, try out the 18-hole championship golf course designed by Pete Dye. An impressive infinity pool looks out over the golf course and woods, enticing guests to make plans for a dip and sunbathing. As in the old days of taverns and inns, relaxation is part of leaving the road behind and slowing things down. The spa at Keswick Hall is the place to unwind and let the staff take you on a journey of mind and body bliss.

The golf course at sunset seemed like a great place to be. Photo by Kurt Jacobson

Star Chef

I’m not often impressed with star chef’s outposts, but Marigold by Jean-Georges wowed us with appetizers, entrees, and a timber-beam constructed dining room.  We started with the complementary bread and olive oil. The focaccia was amazing. Next was the warm seafood salad with shrimp, calamari, scallops, and clams with a lemon-shallot dressing.

Marigold has one of the best Plant-Based menus I’ve seen in a non-vegetarian restaurant. We loved the roasted cauliflower with turmeric and tahini sauce. This is the cauliflower that all cauliflower dishes shall be compared with in the future. The lobster and corn pizza had plenty of tender lobster chunks and not too much cheese, making it a winner.

The Best roasted cauliflower I ever had! Photo by Kurt Jacobson

As a nod to Keswick’s fox hunt history, the property is dog-friendly, allowing up to two dogs per room—under 75 pounds—$250 per stay. Keswick Inn is fully ADA-accessible.


While working on a story about Charlottesville, I saw The Inn at Willow Grove from the highway as I drove into Orange. The Inn was formerly a private home, then later a B&B. When David and Charlene Scibal saw a for sale sign, they pulled off the highway to look at the historic property. Within 24 hours, they had signed a contract to buy the Inn.

The 1770s home, formerly owned by surveyor Joseph Clark, would become the luxury Inn of the Scibal’s dream. Willow Grove was placed on the National Register of Historic Places in 1979. The property has seen Civil War action in its day and has been one of the grand homes in Orange. The Scibals dedicated two years, a ton of money, and a vision for a one-of-a-kind Virginian Boutique hotel, restaurant, and spa.

The Inn at Willow Grove is a gorgeous 1770s-era home and cottages. Photo by Kurt Jacobson

I’ve stayed at the Inn at Willow Grove twice, but the spa wasn’t open on my first visit. Ten guest rooms, ten luxury suites, and five premier suites and cottages await your selection. One of my favorites is The Butler’s Cottage, with its private porch, soaking tub, king bed, sitting room, and fireplace.

The Creekside cottages have five rooms each, offering a balcony or patio looking out over the field, creek, and woods. We stayed in #8 and loved the private balcony facing the woods. The turndown service at night and morning coffee with fresh beignets delivered to our room were classy touches.

Our room in the creekside cottage was quiet and comfortable. Photo by Kurt Jacobson

Fine Dining

The onsite restaurant Vintage, as is the adjoining pub, is open to the public. The Forbes Travel Guide rates Vintage four stars, and I agree. For our recent dinner experience, we had excellent food and wine in one of the semi-private dining rooms.  An amuse bouche and bread and butter started the meal off perfectly.

For a starter, we ordered the cheese platter that was not only beautiful but filled with taste treats like cornichons, sliced strawberries, Marcona almonds, three delicious spreads, blackberries, blueberries, dried apricots, three cheeses, and the best crostini ever.

The cheese platter at Vintage was amazing. Photo by Kurt Jacobson

We were given ample time to savor our wine and cheese platter before our entrees arrived. The braised rabbit served open-ravioli style with sweet corn was wonderful, but the smoked pork tenderloin will be remembered for years. This tender pork was paired with grits, BBQ carrots, apple, cabbage, and mustard sauce. There was so much pork we took some home and made an excellent pork and home fries meal the next night.

Millhouse Spa

The spa and pool are part of the reason to visit The Inn at Willow Grove. Our massages in the couple’s room were exceptional. The couple’s room has its own relaxation section that was so pleasant I fell asleep 15 minutes before the massage. Our therapists were excellent, and we wished we had booked the 80-minute frangipani hot stone massage instead of the 50-minute version. Several other treatments, like the hot bamboo and deep tissue massage, looked enticing.

The Millhouse Spa will spoil youth with a massage or other treatments. Photo by Kurt Jacobson

Other reasons to visit are for special events either outdoors or in one of the indoor spaces. The Barn can accommodate up to 182 attendees with an outdoor tented space, The Ruins, offering additional room. A stroll on the Inn’s walking paths offers a peaceful after-dinner meditation. The historic town of Orange is just minutes away, as is the James Madison Museum and, a bit further, James Madison’s Montpelier.

I spied this old springhouse on my after-dinner walk. Photo by Kurt Jacobson

The Inn’s Carriage House East is ADA-compliant and has a spa-style bathroom. The Millhouse Spa and Vintage Restaurant are also ADA-compliant.


Barboursville Vineyards owns the 1804 Inn & Cottages and 870 acres, once owned by Governor James Barbour. The 1804 Inn is a classic Georgian Villa that was a stunning home in its day and is now a fabulous place to stay. What was previously a home was opened as the 1804 Inn in 2005.

Front view of the 1804 Inn. Photo by Kurt Jacobson

The Barboursville Ruins are close to the Inn and look like something out of Gone With the Wind. The home, designed by Thomas Jefferson, was built a generation after the 1804 Inn and burned on Christmas Day, 1884. What‘s left of the house are exterior brick walls, interior walls, four massive chimneys, and four columns in the front and back of the home.

The historic Barboursville ruins are still standing. Photo by Kurt Jacobson

I stayed in the Octagon Suite, one of three suites at the Inn, and my bedroom was a short stone’s throw away from the Barboursville ruins. Though close to the ruins, my suite was worlds away from the destroyed, burnt home and was fit for a governor. All three suites at the 1804 Inn will spoil you, as will the three cottages.

Excellent Amenities

The amenities are too numerous to list here, but my favorites were the large well-appointed bedroom, 45-foot private deck overlooking the pasture, vineyards, mountains, and ruins: a luxurious claw foot tub/shower, bathrobes, king poster bed with 400 thread count sheets, complementary bottle of wine, and a full breakfast in the dining room of the 1804 Inn, or in your room by request.

I loved the Octagon Suite with a spacious bedroom and extensive meadow views. Photo by Kurt Jacobson

Add to all the above reasons to stay at the 1804 Inn, the winery, and Palladio. Barboursville Vineyards produces some of the best wines I’ve had during extensive winery visits in the Mid-Atlantic region. Their fiano, sangiovese, cab franc, and Octagon are wines I look forward to tasting each time I visit. Palladio is their fine dining restaurant open for lunch and dinner with Michael Clough, executive chef in charge. Don’t miss the soft shell crab entrée, available in season.

Palladio serves lunch Wednesday through Sunday and dinner on Friday and Saturday nights to pair a meal with their wines. Check out their special feasts held throughout the year. Barboursville lists descriptions and prices for the truffle dinner, Italian harvest Feast, and other delicious themed feasts on their website.

We had one of the best versions of Maryland soft-shell crab ever at Palladio. Photo by Kurt Jacobson

The Malvaxia suite is ADA-compliant, as are the winery’s tasting rooms, Palladio, and one of the decks overlooking the meadow.

Middleburg, Oldest Historic Inn of Virginia?

The oldest inn I’ve visited is the Red Fox Inn & Tavern in Middleburg, VA. The Red Fox Tavern began operating in 1728 as an inn and is still functioning as such. Built of local fieldstone, the building occupies the corner of E. Washington and Madison Streets. Although only four stories tall, the Red Fox seems to tower over the intersection that has seen horse and buggy traffic change to gas-powered automobiles and, lately, plenty of electric vehicles. Old as it may be, the Red Fox Tavern holds its own in a modern era with five tavern suites above The Tavern and Night Fox Pub.

The Red Fox Inn is one of the most distinguished buildings in Middleburg. Photo by Kurt Jacobson

The rooms are found in whimsically named parts of the property. Red Fox is the name granted the five rooms in the historic main building. Each room is unique, and all have original fireplaces and flooring, giving the feel of a Louisa May Alcott novel.

More Than One Fox

A short stroll from the Red Fox is The Stray Fox, with seven rooms, two cottages, and a well-kept courtyard garden. The two-room suites, Belmont and Rokeby, could rival some of Washington DC’s best luxury hotel rooms. Luxurious touches like a living room with a wet bar, dining area, manicured garden, covered patio, and a deluxe walk-in rain shower will spoil the lucky guests who choose one of these suites.

The Carriage House continues the luxurious lineup, offering three professionally decorated suites. The Fox Den and Middleburg Cottage round out the lodging choices. The Middleburg Cottage is perfect for a family with a two-story layout, including two bedrooms, two bathrooms, a dressing room, a walk-in closet, a kitchen, a dining room, and a walled courtyard.

The cottages at the Red Fox Inn are cute as can be. Photo by Kurt Jacobson

Fine dining with wines from near and far are offered at the Tavern, and a caviar and champagne menu is available.  The Night Fox Pub offers a small but tasty menu of above-average pub fare like a duck fat seared tenderloin sandwich, blackened salmon salad, rainbow trout, and more. An extensive wine list shows off the best of Virginia wineries and has dozens of old-world and new-world wines on the list.


The Wayside Inn says it’s the oldest continuously run Inn in the United States. Their website states, “The oldest part, the “Old Kitchen” was built as a waystation and stagecoach stop in the 1740s,” and is still part of the Inn that has seen wars, fires, and famous people. Though initially a small country inn, The Wayside Inn is currently offering a choice of 22 guestrooms. That’s a significant change from 1797 when the inn formerly known as Wilkensen’s Tavern provided lodging and food for travelers.

Historic Kitchen at the Wayside Tavern. Photo by Piers Lamb

The Wayside Inn was spared the torch when the Civil War brought military action to its doorstep. Both the North and the South were treated well by the Inn’s owners during the war years. Middletown and nearby Winchester saw lots of military action and reversal of either side’s possession of battlefields. The Wayside Inn’s website states, “The Inn survived unscathed due to the readiness of the day’s victor controlling the inn that day. Civil War buffs will find many historic battle sites in the area and can stay where many soldiers and officers ate or lodged during the war.

Front view of Larrick’s Tavern in Middletown, VA. Photo by Kurt Jacobson

Jacob Larrick’s name still graces the sign in front of the Inn. Larrick bought around the Civil War era before owners Maggie and Samuel Rhodes became owners. As the roads improved, the Inn became one of America’s first Motor Inns serving a new kind of traveler.

Gentlemen’s parlor at the Wayside Tavern. Photo by Piers Lamb

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Last Word About Historic Inns of Virginia

A road trip to one of these inns will leave you with memories of Virginia’s countryside hospitality. I highly recommend you try at least one of these historic inns of Virginia in the spring, summer, or fall. We invite you to explore Wander With Wonder for more of our favorite historic hotels and more to do while visiting Virginia.

The best way to experience Virginia’s countryside hospitality is to take a road trip to one of these inns. Read on for our favorite historic inns of Virginia. | Historic Inns | Virginia Inns | Luxury Hotels | Boutique Hotels


Historic Inns of Virginia: A Taste of History

Written by Kurt Jacobson

Kurt Jacobson is a former chef and current freelance travel writer. His writing covers restaurants, destinations, hotel features, farms, and wine. When not hanging out at home Kurt loves exploring the Mid-Atlantic area with his wife and dog Sophie. Kurt's published articles can be found at Trip101.com, GoNOMAD.com, Mother Earth News Magazine, Edible Delmarva Magazine, tasteoftravel2.com, and 40+ publications worldwide. Find Kurt online on Twitter at @KurtTravels2 and follow his website http://tasteoftravel2.com/.

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