The Wayside Inn: A Historic Weekend Getaway from Washington, DC

I was invited for a complimentary stay and ghost tour at The Wayside Inn in exchange for this post. All opinions are my own.

The Wayside Inn in Middletown, Virginia has been welcoming travelers since 1797, making it the country’s oldest continuously operating inn. A visit here quickly transports you back in time where, unlike a museum back in the city, you can sleep, eat, and sit in the same rooms as Thomas Edison, Lucille Ball, James Earl Jones, Charles Lindbergh, Franklin and Eleanor Roosevelt, and more. The halls of the Wayside Inn hold centuries worth of stories from both famous faces and the average travelers. In fact, when I mentioned my parents honeymooned at the Wayside Inn in the 80s, they said they hear stories of guests’ relatives visiting decades ago all the time. So naturally, you can feel the history around every corner. And you might find that some of the spirits of past travelers have never really left.

Sections of the Wayside Inn have been standing since 1742 but the building wasn’t an inn until 1797. Before that, it was just a waystop or a more informal rest stop for travelers. Much of The Inn we know today is thanks to Maggie Rhodes who purchased the inn in 1904 and completed renovations in 1917. Her husband Samuel took the credit but Maggie is the visionary that took The Inn into this new era.

The Wayside Inn also features both a Gentleman’s and Ladies Parlor reflecting the decor and traditions of the time period. The Ladies Parlor pays tribute to the hobbies and art ladies would have practiced during this time and the Gentleman’s Parlor includes a sneaky entrance to the speakeasy used during Prohibition. Take the history tour for a closer look and to see where they hid the liquor!

During your stay, spend some time at Clem’s Kitchen where you can still see parts of the kitchen that served as a waystop in 1742. There is something remarkable about having a drink in the same spot George Washington likely passed through. The walls are still standing, the original well is still there, and we’re still doing the same thing humans have done for ages: sharing stories over a drink. It’s a magical connection to history you can only find in places like the Wayside Inn.

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What to Expect

Each room at the Wayside Inn is uniquely decorated and honors the styles from Maggie’s renovations. We stayed in the beautiful Bernstein Suite which included a separate sitting area and sunroom. The suite is a beautiful option if you are looking for a unique, romantic getaway with a little extra space.

There are multiple sleeping arrangements so you can also visit The Wayside Inn with as a family. Several rooms feature multiple bed layout outs including queen beds, twin beds, 3/4 beds, and full beds. The Inn features 22 guestrooms with no room 13 or 10. I suspect this is part superstition and part lost to history during the renovations.

During your stay, ask the front desk about a ghost tour to get a deep dive on the history of The Inn. You’ll hear more than just the famous names that have stayed here. The Wayside Inn also tells the stories of the Black men and women whose labor and presence shaped this place, and honors women like Maggie whose vision actually built the place, even if her husband got the credit at the time. It’s the kind of history that feel more complete and honors everyone who made it special.

When to Go

The Wayside Inn is open year-round, and each season offers different benefits and charm.

Spring is one of my favorite times to go because you can enjoy the nice weather before the heat of summers sets in. Take a hike or sip wine outside as the tress regain their leaves.

Summer brings the most activity in the area, but also the heat. Just be mindful to plan hikes early in the morning to beat the heat. Check surrounding county websites for local fairs, festivals, and more. The Middletown 4th of July Parade goes down Main Street and is announced directly from Wayside Inn!

Fall is when the Shenandoah Valley truly shines with colorful foliage. Hiking is at its best and the wineries are in harvest season. Plan your trip around Reenactment Week in October if history is your thing. The Cedar Creek Battlefield comes alive with living history events.

Winter is quieter and cozy. The Wayside Inn decorates for the holiday season and you can catch the Middletown Holiday Parade on Main Street. After the holidays, visit during the winter for a cozy escape warming up next to the fireplaces or with the drink in Clem’s Kitchen.

Restaurants

There is a wide variety of locally restaurants to enjoy while you are in town. In the morning, walk just a few steps down the street to The Daily Buzz which offers great coffee, acai bowls, and hearty bagel sandwiches.

Another can’t miss brunch option nearby is Vault and Cellar, a women owned spot offering an elevated twist on classic Appalachian favorites. There is an extensive bourbon list and many of the dishes incorporate bourbon flavors. We especially loved the French Toast with bourbon syrup and the bourbon creme that we added to our coffee. Vault and Cellar is also open for dinner.

Things To Do Near the Wayside Inn

My favorite way to spend a trip in this area is outdoors with wineries, stargazing, and hiking. For hiking and monthly stargazing, head to Sky Meadows State Park about 30 minutes away. Big Meadows Lodge and Skyline also offer monthly stargazing programs but are a little bit farther away – about 1 hour.

There are seemingly endless wineries in the area to enjoy both local wine and the beautiful mountain views. A few favorites are Valerie Hill, Fox Meadows Vineyards, Naked Mountain Winery, and Cobbler Mountain Cellars. If beer in more your speed, don’t miss Honey and Hops Brewworks and Box Office Brewery. For a combination of wine and beer options, head to Reitano Vineyards.

Two Virginia classics are within a 30-minute drive. Luray Caverns is one of the most popular caverns on the East Coast and a perfect indoor option on a hot or rainy day. The Virginia Arboretum is free to visit, with walking trails through native plants that make for a peaceful morning stroll.

For nature experiences near The Inn, the Wayside’s own recommendations are worth following: Emerald Pond and Lions Tale Trail in New Market, and Hone Quarry near Rawley Springs are all an easy drive away. Story Book Trail offers beautiful views while Lions Tale Trail is more of a sensory experience for all ages.

Book your stay using code daycation10 for a discount!