A Hauntingly Good Time on DOG Street


Last Halloween I decided to try something new.  My neighborhood that I grew up in seemed to be dwindling in the amount of people that participated in the tradition since I was a child.  We would go and only make a haul of a quarter of our pillow case.  If anyone knows what I mean that isn’t very much.

When I heard that Colonial Williamsburg was doing their first annual trick or treat’ing I was beyond excited.  I adored the revolutionary city and could not wait to walk down Duke of Gloucester in my Halloween finest.   The back drop of the historic city, with its old houses and store fronts would be ideal for beautiful photographs as we strolled down filling our buckets full of sweet treats.  So, I told my good friend Michelle, who celebrates the holiday with us yearly, that we were going and she was all in.

Myself on the left, Caite in the middle, Michelle on the right.

Colonial Willliamsburg blew it out of the water.  My mind was blown by the amount of effort and planning that had gone into the event.  The theme was Blackbeard’s Revenge.  It was surrounded the story of Blackbeard the Pirate and his crew, where some had been tried in Colonial Williamsburg around 1719.

Before that Governor Spotswood had sent troops by sea, led by Lieutenant Robert Maynard, to capture Blackbeard. The troops hid below the deck of an abandoned ship to lure Blackbeard and his men on board.  It worked and the troops surrounded the infamous pirate and his men where a great battle began.

In the end, the Lieutenant and his men were victorious.  Legend says Blackbeard went out swinging, being stabbed twenty times and shot five times during the battle.

“…struck time after time, spewing blood and roaring imprecations as he stood his ground and fought with a great fury.  One mighty arm swung his cutlass like a deadly windmill while the other fired shot after shot from the brace of pistons in his bandolier.” – Donald Shomette

Maynard and his crew defeated the band of pirates on November 22, 1718.  They cut off Blackbeard’s head and threw his body into the ocean.  Eventually they placed his head high on a pole and put it at the mouth of the Hampton River.   Blackbeard may have died in North Carolina, but his crew who surrendered awaited trial in Virginia.

They were kept in Williamsburg’s famous jail, simply called the Public Gaol.  The conditions were very poor.  It smelled, was infected with bugs and rodents, the food was horrible and a disease known as Gaol Fever was not uncommon.

The trial began in March of 1719 at the Capital Building.  Virginians sentenced all but two of Blackbeard’s men to death.  Samuel Odell was acquitted because he had only been on the ship one day and Isreal Hands, Blackbeard’s chief aide, was pardoned.

The remaining pirates are said to have left the jail riding on top of their own coffins to meet their doom.  They traveled down Gallows Road and were hung along what is now known as Capitol Hill Road.   Their bodies were to be hung in cages along the entrance to the city to deter would be pirates and inspire confidence in the justice that was delivered.

Sounds can be heard from what locals will call a wagon of death making its way down Capital Landing Road.  They claim to have heard a horse and cheering from a crowd.  Back then, hangings were public and people would come and shout and jeer at the accused.  They would have the wagon roll out from under them to swing from the gallows.  The sad part is, it wouldn’t always kill them right away.

There have also been sounds reported coming from the Public Gaol.  Voices and heavy footsteps come from a deserted room on the second floor or moaning and whispers late at night.

Needless to say, Colonial Williamsburg is probably host to a lot of spirits, both restless and friendly.  It has a long, rich history and it is beautifully maintained, not just the buildings but the stories of old.

Caite in the Revolutionary City

So, back to the fun, kid friendly part of this posting.  Last year, Williamsburg had two nights of trick or treating available during the early evening hours of the weekend of Halloween.  Kids of all ages would be able to walk DOG Street and trick or treat with their parents.  The best part of this event is that trick or treating is free.  Yes, it is a free event hosted by Williamsburg and Mars candy (registration required). Bite sized candy bars and tangy starburst filled my daughter’s bag.  They had blocked off half of Dog Street and every few houses or stores they would have people handing out sweet treats in costume.  They were Colonial costumes but spooky.


Trick or treating

Skeletons and decorations were littered all over the city.   I don’t think we saw one corner of that street that didn’t have some sort of scene set up.  I couldn’t stop taking pictures.  They had stands set up with cider, soft drinks and the best hot chocolate I have ever tasted.

The city does offer kid friendly fare at their local restaurants as well as more tasty treats like cookies and cakes at their vendor stands.  We bought a commemorative cup in the shape of a skull to get refills all night.

They had an area set up to paint and color stencils of pumpkins, live stories being told or past ghost stories, the history of Blackbeard and even an appearance by the dreaded pirate himself.

Horses were painted like skeletons that rode through the streets and games were set up to earn tokens to win prizes.  It was perfectly done and young and old enjoyed the great time had by all.


Williamsburg does offer a more adult haunting down DOG Street after dark.  But, as we had a five year old we didn’t attempt to stay too long after the sun went down.  But if you are looking for safe family fun this Halloween, look no further than Colonial Williamsburg.  They have now extended their haunting to four nights this year.   Trick or treating is still free with registration and a small fee per person who would like to participate in more activities than just collecting candy.  Worth every penny!

So, this year we will be back at it again.  Blackbeard is now cursed by a sea witch and the haunting on DOG Street will continue!

Thanks for reading!


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s