Top Ten Most Haunted Places in Annapolis

Nestled on Chesapeake Bay’s shores, Annapolis, Maryland, boasts a rich history dating back to 1694 when it became the state capital. It earned the “Athens of America” moniker as a hub for colonial discussion, where luminaries like George Washington gathered. But beneath its stately Georgian homes, a hidden world of secrets brewed.


The city played a crucial role in the Revolution, hosting the Continental Congress and George Washington’s resignation. In the 1790s, Annapolis declined as Baltimore rose. A resurgence during the Civil War saw the U.S. Naval Academy’s arrival and wartime shipyards.


In the ’70s and ’80s, preservation efforts brought the past to life, unearthing tales of betrayal and tragedy. From the James Brice House’s haunting past to spectral encounters in taverns like Middleton’s and Reynolds, Annapolis weaves a tapestry of history and the supernatural, transcending time itself.


Today, we embark on a journey through one of the most densely haunted cities in the nation. In Annapolis, the spirits are far from shy, and you may witness orbs, shadows, or even full-bodied apparitions. Skeptics have been known to leave this tour with newfound beliefs. So, without delay, let’s venture to our first chilling destination.

Middleton Tavern

Middleton Tavern, Maryland’s oldest bar, is a living testament to centuries of history and the shadows it has cast. Established in 1750 as a humble “Inn for seafaring men,” its doors swung open to a more distinguished clientele, including the hallowed figures of George Washington, Thomas Jefferson, and Benjamin Franklin. Burdened by the weight of his role in history, Washington likely sought solace within these timeworn walls in the days leading to his poignant resignation from the Continental Army in 1783. 


Middleton’s storied past unfolded through different iterations, transitioning from an inn to a general store, a meat market, and finally to a cherished tavern. Its true revival occurred in 1968 when a young Jerry Hardesty, aged 26, undertook its stewardship.


Hardesty not only restored the tavern’s former grandeur but its original name, “Middleton Tavern,” – a name intrinsically linked to the venue’s modern legend. With his arrival came the introduction of the legendary “Middleton Oyster Shooter,” an iconic shot glass adorned with a freshly shucked oyster, crowned by in-house cocktail sauce, and laced with a hint of vodka. 


Yet, it’s not only the delectable history that haunts these old timbers, for Hardesty, an embodiment of Annapolis itself, believed Middleton’s was imbued with spectral residents and their lingering tales of the beyond.


A Resident Spirit


In Middleton’s dimly lit top-floor bar, a colonial phantom known as Roland Johnston lingers as a foreboding presence. His ghostly appearance infuses the room with the pungent scent of spectral cigar smoke. However, Roland is far from a passive specter; he revels in malevolent mischief. He’s known to send glasses cascading from their shelves, topple wine bottles, and cast electronic devices into disarray, casting an eerie aura over the historic tavern.


The ghostly tale of Roland Johnston took root in the 18th century when he was a spirited, cigar-smoking regular who took pride in his annoyance of both staff and patrons. Roland’s haunting began with skepticism, epitomized by Mike Conroy.


But doubt gave way to dread one fateful night in 2019 when the apparition materialized and inexplicably vanished before Mike’s eyes. This legend, born through a séance in the 1990s, revealed the identity of a troublesome 18th-century patron who continued to haunt Middleton’s even in the afterlife.


Today, a bone-chilling atmosphere prevails, where shadowy figures, cloaked in centuries-old mystery, glide ominously through the dimly lit dining room. Tables and chairs, seemingly guided by invisible hands, shift and creak, their movements defying explanation. 


Who Else Haunts Middleton Tavern?


Even in death, the charismatic Jerry Hardesty, who presided over Middleton Tavern for over half a century, might still play a role in this spectral ensemble, casting an eerie presence long after passing in 2021.

The Governor Calvert House

Governor Calvert Inn, named after Captain Charles Calvert, who governed Maryland from 1720 to 1727, holds a rich history and a share of frightening tales. During his rule, religious tensions ran high between Protestants and Catholics. 


In 1734, after his term, Calvert acquired this property and constructed a single-story brick house, notably featuring a greenhouse for cultivating oranges. Sadly, Calvert’s life ended prematurely in 1734 at the age of 42, leading to the demolition of the greenhouse. Today, a glass floor serves as a reminder of the old hypocaust.


Over the years, the house changed hands, surviving fires and transformations, including its use as barracks during the Revolutionary War. It wasn’t until Paul Pearson’s efforts in the 1970s that the historic structure began its revival. Despite the financial challenges and personal setbacks, Pearson’s commitment to preservation persisted until his passing in 2001.


A Nightmarish Episode


Now, The Governor Calvert House teems with the echoes of its past, and guests have continuously reported creepy encounters. Paranormal investigators believe that spirits from different eras still inhabit its halls, with some observing from the shadows and others interacting with the living. One room, in particular, has garnered attention: Room 3202, where an Ohio couple experienced a nightmarish episode during the COVID-19 pandemic. 


Their shared dream of violence and a malevolent entity led them to believe the room was haunted. Dominic, the hotel’s resident ghost, is suspected of playing pranks, such as turning on the TV at night. A more sinister presence connected to a gruesome murder in the 1940s may also lurk within these historic walls, leaving guests to ponder the identity of the figures they encounter in the dead of night.

James Brice House

Welcome to the James Brice House, Annapolis’s most haunted mansion, where the chilling tales of murder, torture, hoodoo, and curses echo through its storied halls. This Georgian-style masterpiece, built in 1774, is a testament to James Brice‘s meticulous architecture and illustrious career as a Revolutionary War colonel, alderman, mayor of Annapolis, and acting governor of Maryland. 


While its elegance may capture the admiration of historians, beneath the surface lies a complex history of slavery and a dark legacy.


Intriguingly, hidden within the house’s walls, archeologists uncovered a trove of hoodoo charms, a form of folk magic that emerged from the fusion of West African and Christian beliefs among enslaved Africans. Slaves practiced hoodoo in secret, using everyday items like coins, buttons, beads, and matchsticks to perform rituals seeking protection and healing. 


These rituals often centered around fireplaces and doorways, forming a mystical crossroads between the physical world and the realm of spirits. The nature of their pleas remains shrouded in mystery, but it’s a testament to the hardships they endured.


An Unsolved Murder


The Brice House is home to over a dozen spirits, each carrying their own enigmatic story. The most infamous is the “crying girl,” whose heartbreaking sobs have resonated throughout the basement for decades despite the discovery of her remains. Thomas Brice, the victim of a gruesome and unsolved murder, is said to reenact his tragic demise in the library. 


After his death in 1801, James Brice himself was spotted by various witnesses, perpetually surveying his beloved house. While he doesn’t engage with the living, his ghostly presence continues to roam its rooms, sending chills down the spines of those unlucky enough to catch a glimpse of the spectral former owner. 


More Hauntings at James Brice House


  • General hauntings: Chilling cold spots and moving objects create an unsettling atmosphere.
  • Malevolent aura: Certain areas exude a sinister presence, hinting at a darker legacy.
  • Hoodoo rituals: The house’s former enslaved inhabitants performed rituals that may have unintentionally unleashed unearthly forces.

Little Brice House

Another intriguing piece of Annapolis’s history, The Little Brice House, has its own share of hauntings and mysteries. This house belonged to James’s father, Judge John Brice, a wealthy planter and politician who played a significant role in James’s life, providing him with the funds and land to construct the more famous James Brice House. 


However, it’s not just its association with the Brice family that makes this house interesting; it has a haunting tale dating back to 1741.


The Hauntings Begin in Annapolis


One of the earliest recorded hauntings in Annapolis centers around John Brice’s experience in this house. In 1741, while entertaining a young woman named “Miss Turner,” an unnerving event unfolded. Turner left the bedroom to retrieve her locket and was met with a violent coldness and a shadowy presence in the parlor. 


An elderly woman, Ariana Jennings, John Brice’s mother-in-law, sat in an armchair by the fireplace. Her appearance was ghastly, with yellow bandages covering her body, revealing blackened sores. This was especially perplexing as Ariana was supposed to be in Britain visiting family and had not indicated any plans to return. 


The spirit’s sudden gaze at Miss Turner sent shivers down her spine, and the room grew colder still, leaving her in a state of panic. She fled and informed John Brice, who later received a letter confirming that Ariana had died of smallpox at the exact date and time Turner saw her.


More Hauntings at the Little Brice House

The Halligan family, who owned the house from 1917 until 2023, also had their share of encounters with the otherworldly. Kay Halligan, the daughter of Katrina Loomis Halligan, experienced strange occurrences throughout her childhood.

In 2005, she awoke to find a wispy figure resembling her deceased grandmother standing by her bed. Despite the unsettling sight, Kay was familiar with the house’s history and calmly greeted the apparition before going back to sleep.

The Headless Tormentor of Cornhill Street

With its ancient foundations and dark history, Cornhill Street is a place where shadows tell tales of woe. This eerie road, connecting East Street to the harbor’s historic fish markets, conceals the chilling story of the headless ghost that haunts it.


In the sweltering summers of the 1770s, disease and despair gripped the city of Annapolis. Fevers, smallpox, and death lurked in every corner. It was during this time that tragedy struck a family on Cornhill Street. A deadly infection claimed the lives of the parents, leaving their two sons orphaned and alone. The elder brother took on the role of guardian, but without parental guidance, the boys spiraled into darkness.


Their inheritance was squandered on spirits and vice, transforming their home into a den of debauchery and chaos. Neighbors, tormented by the ceaseless noise and disturbances, finally had enough. They confronted the younger brother, demanding an end to the madness. When they inquired about the elder sibling, the young man claimed his guardian had left for Baltimore. The disturbances ceased, but a putrid stench soon filled the air.


The Tale of The Missing Skull


An unbearable odor hung over Cornhill Street, tracing its source to the brothers’ dwelling. In the basement, the horrified neighbors uncovered a shallow grave containing the elder brother’s body, headless and mutilated. The younger brother confessed to a fatal accident during a drunken brawl, leading him to dispose of the body in a gruesome fashion. The head remained missing. Justice was served, and the house was cleansed, but the tale did not end there. 


Late at night, the sound of phantom footsteps on Cornhill Street echoes, and the headless specter prowls in search of his missing skull, a ghoulish presence that sends shivers down the spines of Annapolis residents.


It’s said that when a corpse lacks its head, its spirit relentlessly hunts for its missing part. For generations, the headless phantom has wandered the streets of Annapolis, seeking his lost skull, believed to rest somewhere in the dark waters of the Annapolis Harbor. Beware the late-night streets, especially near the Annapolis waterfront.


If you must walk these cursed lanes after midnight, be sure to wear your running shoes, for you may find yourself pursued by the relentless and decapitated spirit of Cornhill Street.

Reynolds Tavern

Reynolds Tavern, nestled in Annapolis, boasts a rich history dating back to 1747. Originally a hattery operated by William Reynolds, it also housed one of the city’s earliest taverns, known as “The Beaver and Lac’d Hat.”


These 18th-century taverns were multifunctional, serving as visitor centers, hotels, and more. Interestingly, women like Mary Reynolds played a significant role in this thriving business; they could run taverns, drawing on their culinary and caretaking skills. 


Mary, William’s third wife, was a standout hostess. Her impeccable housekeeping and memory of guests’ preferences attracted patrons who sought her warm hospitality. While legends hint at admirers like George Washington frequenting the tavern, these claims remain unverified.


There’s Something About Ghostly Mary


When William Reynolds passed away in 1777, the tavern transitioned to Mary and her daughter. Mary’s death in 1785 marked the beginning of her ghostly presence. Her apparition has been spotted throughout Reynolds Tavern, silently observing its various transformations over the years. 


However, it wasn’t until the mid-1980s, during Paul Pearson’s restoration of the tavern, that Mary’s spirit became particularly active. In death, Mary retained her strict, no-nonsense persona. Phantom hands would rearrange cutlery if tables were improperly set, and vases would tip if a table required cleaning. 


Mary’s spectral manifestations turn sinister when confronted with rowdy or disrespectful guests. Her vengeful tactics intensify, striking fear into those who cross her path. She becomes relentless, spilling drinks with a malevolent force, imprisoning patrons in the bathroom, and plunging the room into suffocating darkness as lights flicker, all in response to profanity or disrespect. Those who encounter her are left with a lingering, bone-chilling sense of dread.


Those who visit Reynolds Tavern today are well-advised to mind their manners, as Mary’s ghost remains an enforcer of her rules, ready to provide an unforgettable ghostly encounter for those who don’t adhere to her standards.

The Maryland Inn

In the heart of Annapolis, the Maryland Inn stands as a living relic, carrying with it centuries of chilling secrets and ghostly encounters. Built in 1772, it’s not just a hotel; it’s a portal to the past, where each creaking floorboard and dimly lit corridor holds stories that can send shivers down your spine.


You see, beneath the inn, a sinister secret tunnel slumbers in its old wine cellar. Lost to time, its purpose remains a haunting enigma. Was it a passage to the Maryland State House, offering a desperate escape during tumultuous times, or a web of darkness that concealed sinister activities like bootlegging and abductions? The tunnel’s echoing whispers continue to vex those who dare to explore its depths.


Specters of Love and War


But it’s not just the underground that’s teeming with the supernatural. The Maryland Inn harbors a host of spirits, each with a tale more heart-wrenching than the last. Among them, “The Bride,” a tragic figure forever clad in white, paces room 405, a ghostly reminder of lost love. In the taproom, a 19th-century naval captain still lingers, savoring his pipe and raising a spectral glass to unseen patrons. 


Up on the dreaded fourth floor, echoes of ghostly arguments and unsettling noises resonate, and shadows of Revolutionary War soldiers and a mournful woman in black haunt the hallways. This is the Maryland Inn, where history’s darkest moments are etched into its very soul, waiting to terrify those who dare to uncover its spectral secrets.

Brooksby-Shaw House

The Brooksby-Shaw House, constructed between 1720 and 1725, bears witness to a haunting tale that spans centuries. Cornelius Brooksby, the town butcher, dreamed of this house but passed away a year before its completion. His widow, Mary, swiftly remarried, and this decision ignited a haunting that has persisted for generations. 


Cornelius’s vengeful spirit made its presence known with relentless disturbances, including pacing footsteps, shattering glass, and loud bangs. Even a misty apparition of Cornelius himself appeared, casting a furious glare upon Mary’s new husband, Thomas Gough.


The torment escalated as Thomas experienced sleep disruptions, physical assaults, and a relentless barrage of poltergeist activity. Unable to endure the relentless haunting any longer, Mary and Thomas abandoned the house, leaving it in the hands of Cornelius’s granddaughter, Mary Brooksby-Long. Unfortunately, the younger Mary and her husband were also subjected to relentless unearthly assaults, ultimately prompting their departure. 


The house remained vacant until 1784 when John Shaw, a respected cabinetmaker and caretaker of the Maryland State House, took residence. Curiously, Cornelius seemed to spare Shaw from his vengeful antics, granting him years of tranquility in the house.


Return of the Restless Spirit


The house had various occupants over the years, including an Elks lodge and legislative offices, but Cornelius’s spirit continued to stir at night. Security guards patrolling the building often encountered inexplicable occurrences. One notable incident involved a beautifully adorned Christmas tree being mysteriously destroyed, with glass ornaments shattered and then miraculously restored to their original positions. 


Another encounter saw a guard facing a brooding, dark figure that suddenly vanished, leaving him in a state of shock. These unsettling incidents continued to haunt those who entered the house, leaving a legacy of otherworldly mystery that persists to this day. The house is now under the care of Historic Annapolis, and its restoration efforts may hold the key to calming Cornelius’s restless spirit, though only time will tell.

Shiplap House

The Shiplap House, dating back to 1715, serves as a chilling testament to its tumultuous history, rife with hauntings that have persisted over centuries. Originally a tavern run by Edward Smith and Mary, it later passed into the hands of John Humprey, who renamed it the “Harp and Crown.” 


However, the most intriguing tale within its walls centers around Adrienne, a young server who met a horrific end. Adrienne, renowned for her beauty and numerous marriage proposals, eventually resorted to offering certain illicit services to increase her income. Tragically, she was found bludgeoned outside of the tavern. Her murder remains a mystery, and her restless spirit is said to still linger within the Shiplap House.


Ghostly Encounters


The Shiplap House has seen its fair share of unexplained activity over the years, with numerous sightings and otherworldly phenomena. Renowned painter Francis Blackwell Mayer, during his residence in 1877, frequently encountered Adrienne’s apparition in the backyard. However, it was his terrifying encounter with her while lying in bed, believing her to be his wife, that etched fear into his memory. 


The room suddenly filled with the scent of floral perfume, and he realized the figure next to him was icy cold and unresponsive. The sinister figure disappeared only after his real wife, Ellen, arrived from downstairs. Mayer’s torment continued, with phantom touches and even the mysterious appearance of “Adrienne” written in red lipstick on the mattress.


In 1958, Historic Annapolis acquired the deteriorating Shiplap House, using it as its headquarters. Still, the hauntings didn’t cease. When Donald and Barbara Jackson moved in in 1981, they experienced their own chilling encounter. During a ghost-themed dinner party, guests heard creepy noises and disembodied footsteps


However, the real terror occurred after the guests left. Barbara, lying in bed, felt the floor creaking and then the bed dip behind her. She was inexplicably pushed out of bed by freezing cold feet, and a menacing shadowy figure vanished when the light came on.


More Spirits of The Shiplap House


  • Today, the Shiplap House is home to two other spirits, Mary and Audrey. 
  • Audrey, a young girl in a blue dress, and Mary, her nursemaid, are believed to have perished in a 19th-century epidemic.
  • Audrey primarily appears to children, while Mary lingers in the old nursery and occasionally administers a phantom swat to unruly youngsters.

Old Annapolis Jail

Nestled amidst the vibrant streets of Annapolis, the Dock Street Bar and Grill is renowned today for its delicious crab cakes and Instagram-worthy blue facade. However, this inviting establishment conceals a chilling history. 


Over three centuries ago, it served as the city jail, a place of misery where criminals awaited their grim fates regardless of their crimes. The building’s grim past continues to haunt it, as countless souls from a bygone era linger in the shadows, their stories etched into the very fabric of this historic haunt.


Hope Fades and Spirits Linger


Though it serves as a popular bar and grill today, it bears the weight of the building’s grim history. In the 18th century, this institution housed criminals in squalid conditions. Shackled and chained to dank walls, prisoners faced unimaginable filth, with urine-soaked floors and feces-laden cells. 


Public punishment was the norm, as inmates found themselves locked into stocks and pillories, subjected to the taunts and torment of passersby. An official report from 1766 captured the prison’s horrors, describing it as “so filthy and nasty that it is excessively nauseous.” 


Ghostly figures have been sighted entering the building or standing ominously in front of it, and even chained prisoners have been witnessed walking toward the area where the stocks and pillory once stood. Disembodied footsteps, hoarse whispers, and the eerie sound of ragged coughing have also been reported at the former jail.


Maryland’s history of executions is equally grim, primarily relying on hanging as the method of choice. The 1930 hanging of Jack Johnson, which required two attempts, shocked the public. Newspapers reported these macabre incidents, igniting a growing outcry against gallows executions. The gallows were eventually retired in 1955, replaced by other methods like the gas chamber, and finally abolished in 2005. However, the specters of those dark days continue to cast their shadow. Passersby have reported an overwhelming sense of dread and fear while near the bar and grill, suggesting that the restless spirits of the past project their emotions onto the living.


Discover Annapolis’s Most Haunted


As we embark on this spectral journey through Annapolis, prepare to be enthralled by the otherworldy history that lingers within its historic streets. And when you’re ready to discover Annapolis’s most haunted locations, take a ghost tour with US Ghost Adventures


Our expert guides will introduce you to chilling tales and terrifying encounters that await those who dare to explore the haunted heart of this captivating city.