We love Halloween — it’s a fun holiday that we get to celebrate with parties, candy, and the things that scare us most! Of course, that scary stuff is what Halloween is all about, so it’s become our annual tradition to showcase some of the spookiest places around the United States, and even the world! This series has been around since the Shop & Enroll blog’s first Halloween, and with travel becoming safer and more manageable again, you can actually visit some of these!

This year, instead of showing off several places, we’re picking two that we can really cover in depth. This way, you’ll get plenty of spooky stories to send a chill down your spine, just in time for Halloween.

Whaley House, San Diego, CA

Tucked away in Old Town, San Diego, where the city first sprouted, is a large brick house called the Whaley House. This may seem like a quaint reminder of times past, but it fits right in with the other locations in this series. The Whaley House is reputed to be the most haunted home in the United States. Built in 1857 for the family of Thomas Whaley, the home has served many purposes over the years. It has been a family home, a theater, a courthouse, and a general store.

Through each of these identities, the building has seen its fair share of tragedy. Shortly after moving into the house, one of the young Whaley children died of scarlet fever. Later, one of the family’s daughters committed suicide after marrying a con man who was after the family fortune and left her on their honeymoon. Thomas’s wife, Anna, and their remaining children also passed away in the house. The grounds themselves may be even haunted, considering it was built on the sight of a gallows where a man named Yankee Jim Robinson was hung for stealing a boat. There are also rumors that the property was at one time a cemetery. Keep in mind, this all happened in a very short timeframe, excluding the death of Corrine, the daughter who passed away in 1952.

  • 1852 — Yankee Jim Robinson is hung on the property.

  • 1857 — The Whaley House is built.

  • 1858 — 18-month-old son, Thomas Whaley, dies of scarlet fever.

  • ~1859 — A fire damages a portion of the home, forcing the Whaleys to move to San Francisco.

  • ~1868 — After a massive earthquake, the family moves back to the Whaley House.

  • 1871 — An armed group remove court papers from the home, holding the family at gunpoint.

  • 1885 — Violet Whaley commits suicide after her divorce. The family moves to a new home shortly after.

  • 1888 — Thomas Whaley, the father, passes away.

  • 1909 — Francis Whaley, Thomas’s son, begins restoring the house and moves the family back in, where they all live until their deaths.

In under 30 years, the family relocated twice due to tragedy with turmoil seeming to follow them. It’s no wonder the house has become famous for ghosts. Even the Whaleys reported hauntings while they lived there, telling a local newspaper that they experienced events they attributed to Yankee Jim. Restoration workers reported strange sounds, people passing by saw ghostly figures in the windows, and people in the house felt a powerful, unseen presence. Baby Thomas is also heard in the form of phantom cries and giggles or the noise of tiny feet running across the floor. Violet is seen, felt, and even smelled on the second floor, where she spent much of her time until her untimely death. Modern visitors also experience objects moving on their own, lights turning off and on by themselves, strange images in photography, and all the earlier reported hauntings.

So, if this sounds like something you want to get involved in, how can you go about it? The Whaley House has fully accepted the mantle of America’s Most Haunted House, making them very accommodating to ghosthunters. They host a guided ghost tour at night and an after-hours guided paranormal investigation. Anyone who experiences anything is invited to share their stories on their website! About two-minutes-by-foot away lies the El Campo Santo Cemetery, the cemetery grounds that the Whaley House may have been built on, and it has its own haunting stories.

One if by Land, Two if by Sea Restaurant, New York, NY

From a California home to a New York restaurant, we find ourselves at the One if by Land, Two if by Sea restaurant. The building started its life as a carriage house in 1767, meaning it has seen a lot of history over the years. Sitting in New York City’s picturesque West Village, the old carriage house serves fine dining in a lovely, rustic dining room.

Of all the historic figures associated with the restaurant, none are more closely tied to the building than Aaron Burr. Most famous for his duel with Alexander Hamilton, Burr was the third Vice President of the United States and a major figure in the politics of the early United States. In the 1790s, Burr used the carriage house until his duel with Hamilton, when most of his New York property was seized. Some report that Burr may have even lived there for a time with his daughter, Theodosia. The other great mystery is of the tunnel lying underneath the building leading straight to Hudson Street, where the shore of the river used to be. Little is known about the tunnel, but it was likely used in the Underground Railroad and possibly used during the Revolutionary War and for smuggling throughout history.

Staff regularly experience weird occurrences. Lights flicker. Pictures on the wall tilt. Members of staff have even reported being pushed by an unseen force.

The dining room isn’t the only place that the restaurant delivers if you’re in the mood for something more terrifying. The spirits of Aaron and Theodosia Burr Alston have made their presence known, but they’re only two of 20 ghosts reported there. Staff regularly experience weird occurrences. Lights flicker. Pictures on the wall tilt. Members of staff have even reported being pushed by an unseen force. Some of these phenomena have been blamed on Aaron Burr. Other spirits said to roam the restaurant are that of a woman who broke her neck tripping down the stairs and that of a Ziegfeld Follies dancer whom the staff light a candle for. The woman at the stairs, known as the White Lady, has even been seen descending the stairs. A solitary spirit of a man also likes to linger by the fireplace and is sometimes seen using the front door.

Theodosia Burr is another interesting case. Her spirit has been sensed in the carriage house, though it is not where she died. The beloved daughter of Aaron Burr, Theodosia was a bright, well-respected member of New York Society who lived a fascinating, if tragic, life. She lost her mother at a young age, lost a child to malaria, and helped fund her father’s efforts to create a new country, made up of parts of the Western North American continent and Mexico. Aaron Burr would have become emperor of this country, with Theodosia becoming empress after him. It is her death that creates the most talk today, however.

Whatever the cause, it seems that Theodosia may have made it back to New York in one sense.

In 1812, Theodosia decided to go to New York from South Carolina after the death of her son. On December 31, 1812, she boarded the Patriot and left for New York. The ship, crew, and Theodosia were never seen again. Over the years, hundreds of theories were dreamt up, from Theodosia secretly being alive to dying in a pirate attack. Whatever the cause, it seems that Theodosia may have made it back to New York in one sense. Perhaps the spectral woman seen at the stairs is Theodosia visiting her father? Maybe she is being mischievous by throwing plates to reenact her childhood years in the carriage house? The staff certainly believes that it’s Theodosia who tugs at earrings or plays pranks.

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Both the Waley House and One if by Land, Two if by Sea Restaurant fit in perfectly this time of year. Whether you’re sharing dinner with a spectral Founding Father or spending the night looking for evidence of the paranormal, you’ll get your fill of spooky Halloween fun. Don’t miss out on the rest of our series if you’re dying for more spooky Halloween content!

Further Reading

The Shop & Enroll Blog — Best Spooky Spots for Seniors This Halloween
The Shop & Enroll Blog — More of the Best Spooky Spots for Seniors This Halloween
The Shop & Enroll Blog — Spooky Spots for Seniors for Halloween 2019 (Part 1)
The Shop & Enroll Blog — Spooky Spots for Seniors for Halloween 2019 (Part 2)
The Shop & Enroll Blog — Spooky Spots for Seniors for Halloween 2021
The Shop & Enroll Blog — The World’s Best Spooky Spots for Seniors This Halloween