Williamsburg, Virginia

Originally founded in 1632, Middle Plantation emerged into one of America’s first planned cities after being petitioned as the new capital location of the Virginia Colony from Jamestown. This new city would be renamed in honor of England’s reigning monarch King William III.

The newly proclaimed Williamsburg quickly flourished, becoming the central hub for political, economic, religious, and social aspects of life in Virginia. Being the home to the College of William & Mary, Williamsburg earned quite the educational status, having produced three famous political leaders, Thomas Jefferson, James Monroe, and John Tyler.

Williamsburg served as the capital city from 1699 to 1780.

The first American hospital for the treatment of mental illnesses was established in Williamsburg in 1773.

In 1781, the Continental Army led by General George Washington gathered in Williamsburg for the Battle of Yorktown, resulting in America’s independence.

A pretty significant and happening place for sure; that’s why when many of the eighteenth century buildings and architecture survived into the twentieth century, a vision of preserving this city evolved.  

In 1926, Reverend William A.R. Goodwin, rector of Bruton Parish Church, captained this preservation project.  The good reverend (or Reverend Goodwin) brought this idea to John D. Rockefeller Jr and explained the importance of preserving such a pivotal place. The American financier and philanthropist saw eye-to-eye with the good reverend, and the result was the living historical museum city we know today as Colonial, Williamsburg. 

                                        

It was a cold, dark night.

How cliché, she thought to herself, as she stepped out of the toasty-warm confines of her compact SUV and into the frozen January night. And, truth be told, it wasn’t dark, not visibly, anyway.

The street lamps, coupled with the brilliant full moon, revealed the glow of a cobalt blue sky. Ironically, the huge, luminescent celestial body served as no consolation; it was the Wolf Moon.

Of all nights, she thought to herself.

Taking in a deep breath, she felt the raw winter air rip through her lungs like a dagger. The frigid wind stung her face. She triple-wrapped the scarf around her neck, slid her already cold and stiffened fingers into the gloves, and pulled on her husband’s fleece stocking cap.

Pausing for a moment, she braced herself for what was to come. Feeling a small shiver convulse within her body, she knew it had little, or nothing, to do with the below-freezing temperatures.

Freezing temperatures, Wolf Moon or not, she knew what she had to do. She gave the stocking cap one final tug and headed for Duke of Gloucester Street, the iced-over snow crunching under each step.

“Hey! I know you!”

A voice came from behind a lamppost in front of Bruton Parish Church.

It was my buddy, Denny O’ Rourke, master storyteller extraordinaire and tour guide host for The Original Ghost Tour Company’s Extreme Ghost Tour of Colonial Williamsburg.

(You may remember Denny, also known as D.C. O’Rourke and host of the popular podcast, Hauntingly Yours. )

The Extreme Ghost Tour is a two-hour candlelit walking tour through the streets of Colonial Williamsburg. Stopping at some of the most allegedly haunted locations, these stories are guaranteed to send chills down your spine- January, or not!

Yes, my visit happened to be in late January, and yes, it started out just like this, Wolf Moon and all. This particular time of year in this historic city is a slightly slower season, (even under normal circumstances), and, given my visit also occurred in the middle of a pandemic, the streets of Williamsburg did appear a bit ‘dead.’

In a manner of speaking, of course, Colonial Williamsburg could be defined as a ‘ghost town’ of sorts, only in the one sense that this place is full of them- ghosts, that is!

Being a city that’s well over three-hundred and twenty years old, there’s bound to be a few narratives about its past residents. And Denny knows them all!

Having been in the midst of Colonial Williamsburg for the past six years, serving as a tour guide, sales merchant, historical interpreter, and for the last five years, as a ghost storyteller, Denny not only knows the legends and folklore of this fascinating city but also has personal stories all his own.  When I learned that Denny hosted this year-round tour, I knew it was a must for the Happy Trails Travel review!

I hadn’t been to Colonial Williamsburg since I was a child visiting with my parents. And to be honest, back then, it was my least favorite of our vacation destinations.

Why? You, ask? Only that I was terrified of the place!

The battlefields of Yorktown, certain houses and buildings in Colonial Williamsburg… I was petrified! So much that my parents learned to purposely dodge those areas that seemed to “spook” me. We continued the visits, because well, they loved the place. And revisiting it some forty-ish years later, I can definitely see why.

 My husband and I enjoyed a quiet and casual winter day exploring the grounds of Colonial Williamsburg. The city of Colonial Williamsburg is absolutely charming! I was perplexed at what could have possibly terrified me so badly as a child.

Even during this limited time of year, we managed to browse the shops that were open and were lucky enough to grab a true colonial-fare meal at the only colonial eatery open: the quaint Chowning’s Tavern.

Everything, from the food and drink at Chowning’s, (they’re known for their specialty ales and root beer) to the atmosphere and our very entertaining waiter, was exceptional! (Although, I did experience a rather odd incident in the ladies’ room, but more on that later.)

The Extreme Ghost Tour begins at Bruton Parish Church.

Originally built in 1715, Bruton Parish was one of the many buildings included in Reverend Goodwin’s restoration of Colonial Williamsburg and now models the authentic reproduction of the old church that we see today. Bruton Parish is the second oldest Episcopal church still in continuous use in the United States.

From Bruton Parish, Denny will guide you to the grand Governor’s Palace, where you’ll hear some unsettling facts and findings that happened right on the property.

As you pass along the dark colonial streets, you’ll hear tales of mischievous ghost children who like to toy with employees and hear of a particular shopkeeper that refuses to retire.

The Magazine that once stored the arms and ammunitions back in the day is now not as quiet as one might think.

Then, there’s the unforgettable stop at the Courthouse, which also served as a field hospital and a morgue after the Battle of Williamsburg.

Oh, and there’s also a sweet and sappy (no pun intended) ghost story that involves a specific oak tree.

And then, we approached it, “The Red House.” And I remembered it right away.

According to Denny, it’s the most haunted house in all of Williamsburg, and some claim it’s the most haunted on the east coast.

“There are a thousand and one different stories about this house, and they’re all colorful. Some of them are okay to talk about, and some of them are just downright creepy.”

I’m talking about the Peyton Randolph House. With over thirty-seven plus deaths happening in this house, many that are disturbing tragedies, there’s no wonder why it has the reputation it does. (And quite possibly, why it gave me the spooks as a little girl.)

Denny admits he spends a lot of time here at the Peyton Randolph House, which is also one of the many museum houses open for tours during the day.  

“I think one of us might want to hear some stories about Chowning’s Tavern.”

And that would have been me.

When coordinating with Denny the details of our tour, I told him about our day in Williamsburg and the wonderful meal at Chowning’s Tavern.

In pure jest, of course, I asked if Chowning’s had a resident ghost. I wasn’t prepared for Denny’s answer.

My visit to the ladies’ room at Chowning’s went something like this:

After my husband and I placed our order, I made my way up the steep and narrow stairwell to the top floor landing where the men’s room was on the right and the ladies’ on the left.

I pushed open the thick spring-loaded door and entered, the door slamming behind me. 

The restroom was small, consisting of the sink and mirror area, two bathroom stalls, and a dormer window.

I went into one of the stalls, both of which were empty.

Finishing up, I heard the door to the restroom open and slam shut, indicating another lady patron had entered. When I exited my stall, I realized I was alone, the other stall still empty. There was no mistaking the door to the restroom had indeed opened and slammed shut, just the way it did when I entered.

Puzzled, I opened the door to the bathroom and peeked out to the landing area. There was no one, not even the sound of footsteps descending down the stairs.

I kept the door propped open with my foot (just because) as I washed and dried my hands. Still, no one.

I stood outside the landing area. The men’s room was silent.

There was not the slightest bit of evidence that anyone was on this level and part of the upstairs tavern except for me.

While strange, I was sure there was a logical explanation.

Denny said there was, and it was Dewey Renwick, a proclaimed prankster- from the nineteenth century!

“He liked to lock women in the bathroom here. He got a bit of a chuckle out of it, he thought it was funny. And they say that, to this day, he’s still locking women in the restroom here at Chowning’s Tavern. It happens all the time! What I usually like to tell ladies is this: If you ever find yourself in the restroom at Chowning’s and you can’t get out of the bathroom, it’s probably Dewey. Just tell him to let go.”

Having any prior knowledge of Dewey the bathroom prankster, I most likely would have by-passed my ladies’ room visit altogether! Thankfully, if it was Dewey that opened the restroom door, he showed me some mercy!

There is a bit of a twist to the Extreme Ghost Tour of Colonial Williamsburg that makes it unique from any other ghost tour out there, and that’s Denny’s use of the Spirit Box. Denny offers up the chance to chat with some of his ghostly colonial friends, if you dare!

The stories shared on The Extreme Ghost Tour are an entertaining blend of history, folklore, and true happenings that have been passed down for more than three hundred years. Denny is a phenomenal storyteller, mixing wit and humor in with these, sometimes, ghastly tales!

The Original Ghost Tour is Virginia’s oldest ghost tour and is the second oldest ghost tour in the United States. Other tours they offer are The Original Ghosts of Williamsburg, Yorktown Hallowed Ground, and The Haunted River Cruise.

Reserve your tour today and come get to know the ghostly side of Colonial Williamsburg with

The Original Ghost Tour!

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Check out more tales from D.C. O’Rourke on his podcast. Hauntingly Yours!