Top 9 Abandoned Places in Connecticut

Ossiana Tepfenhart
by Ossiana Tepfenhart

If you’ve ever watched A Haunting in Connecticut, then you already know that this state has a lot of spooky stuff it can offer tourists. Of course, some of the more bone-chilling places in the state aren’t the ones that generally have tours or act as people’s homes. They’re abandoned. And, their stories are incredible. But, which ones are really worth exploring.

The top abandoned places in Connecticut are the Enfield Mall, Downs Road, Hearthstone Castle, and Comet Diner. Other abandoned locations in Connecticut include Holy Land USA, Gay City, and St. Thomas Aquinas School in New Britain.

Connecticut might be a small state, but it packs a lot of history into it. If you’re looking for some thrills and spills, then this article will give you the spookiness (and history) you’ve been dying to read.

The Most Interesting Abandoned Places In Connecticut

This petite state has a lot of ghost stories, with many of them being rather famous. But would you be brave enough to handle these abandoned places?

1. Hearthstone Castle – Danbury

via I95 Rock

Right near the outskirts of Danbury’s woods is a massive castle known as Hearthstone. The castle was built by famed architect Ernest G.W Dietrich, consisted of 17 bedrooms, Italian wood, and eight different fireplaces. It’s fascinating, then, to know that this circa-1899 house would eventually continue to switch hands until the final residents moved out and abandoned it in 1987.

Since the Jennings, the last owners, moved out, the castle was transferred to the city for ownership. Since then, it has started to decay as nature begins to reclaim it. The ceiling has started to cave in and the floors began to sag. Despite all this, it’s still a remarkable structure to see. Demolition plans are underway, so see it while you can.

2. Seaside Sanatorium – Waterford

via Atlas Obscura

Like most other states in the union, Connecticut had several hospitals that served as places for helping people diagnosed with TB during the 19th century. Much like other sanatoriums of the time, Seaside wasn’t particularly kind to the people who were dropped off here. They were exposed to heavy light all the time and had little effective medicine. Patient abuse was rife, and many people ended up dying as a result of the “good doctors” in here.

Though the sanatorium was made in 1925, it didn’t last long in the business. The place shuttered before 1950 and had to be remade into a psych ward. Then, it shuttered again. Now, it just sits by the sea, a testament to how many people often died as a result of bad doctoring.

3. The Comet Diner – Hartford

via Atlas Obscura

Back during the days of bebop and rock, the Comet Diner was the big place to go in Hartford. Decked out in true classic 1950s decor, the diner remains one of the most well-known examples of real retro architecture in the area. Unfortunately, things didn’t work out for this diner. Peoples’ taste in food changed and the diner closed its doors.

The Comet Diner’s current fate is in flux. On one hand, it could potentially be saved if it is designated a historic landmark and given new life. As of right now, the diner’s quirky architecture might get plowed over as a result of developer interests. It all depends on what society chooses to do.

4. Holy Land USA – Waterbury

via Greg Cookland

Most of us who have traveled down I-84 have spotted a massive wooden cross peeking over the hill. This was once the site of Holy Land USA, a Christian-themed amusement park that was once a major tourist attraction. The entire park had rides and educational setups to make the area look like the holy land of Jerusalem. Impressively, this park was the work of a single man who heard voices telling him to do this.

At the peak of its working time, around 40,000 people would visit every year. Eventually, it stopped being popular for one reason or another. Now, the park sits in disrepair. However, it’s still there and there are pending plans to make it come to life again. You can ask the owner of the area if you can get a tour. He’ll usually say yes.

5. Gay City – Hebron

via Damned Connecticut

In history, we see a lot of towns that had promising beginnings but terrible endings. Such was the case with Gay City. Established in 1796 by John Gay and his family, the petite town served as a popular place for people who faced persecution from fanatical Christians nearby. Led by Methodists, the locals held sermons where they would drink heavily and be merry.

By 1811, there was a factory, a mill, and a full-on homestead. It became known as Factory Hollow. Unfortunately, things took a turn for the worse. Multiple fires burned down the factory repeatedly, murders began to happen, and mysterious disappearances of locals ensued. Eventually, Gay City collapsed and all that is left are some stone buildings from the people who once lived here.

Some suggest the area is cursed. Others find it a cool part of history. Regardless, it’s now part of Gay City State Park and you can visit it.

6. Old Boardman Bridge – New Milford

via CTPost

Built in 1888, Old Boardman Bridge is a truss bridge that was meant to extend a road to carry horses and buggies over the local river. Originally, it was there to replace a toll road made of wood that washed away, but it quickly became something a bit bigger. Due to the unique period of time that the bridge was made, it is also one of the only ones in Connecticut to be made of iron.

The iron bridge is no longer officially in use, but it’s still considered to be a part of the National Historic Registry. Besides, it’s good luck to cross an iron bridge, isn’t it? (I think I heard that somewhere…)

7. Downs Road – Hamden

via Abandoned CT

Now, we’ll be honest. We haven’t really been able to find out much about Downs Road. At one point, this road was meant to be a thoroughfare between Hamden and Bethany. And, it was. It was fairly good at what it did, too. However, at one point, the road ended up closed at both ends. It was later completely abandoned.

According to local legends, there is a strange beast that roams around this area. It’s called the Downs Road Monster, but in reality, it doesn’t sound that scary. It’s suspected of being an albino horse or deer. Many others believe that the area is haunted by ghostly children, but this is probably just the tales of teenagers who want to spook their dates.

8. St. Thomas Aquinas High School – New Britain

via Courant

Schools are one of those places that no one ever sees closing, but once in a while, it still happens. In the bustling town of New Bridge, St. Thomas Aquinas is one such place. This Catholic high school is only one of New Bridge’s schools to truly shutter its doors. Unlike other abandoned schools that had rumors of mistreatment, this high school actually had a far more mundane reason for its closure.

Newspaper clippings from the era show that the school just didn’t have much interest at the time. At the highest enrollment period, it had 250 kids. By the time it closed in 1996, it only had around 11 kids in a single grade. Even though the enrollment dropped and the fundraising failed, many people in the area want to see it come back. Unfortunately, there are now plans to demolish the building in hopes of getting more real estate.

9. Enfield Square Mall – Enfield

via MassLive

Okay, hear me out. This is technically not entirely abandoned, but it is a dying mall and we really enjoy the vaporwave aesthetic here at Upgraded Home. Enfield Mall was once one of the biggest shopping centers in Connecticut. The massive mall took a major hit during the Great Recession. Thanks to the pandemic and the growth of Amazon, it never fully recovered.

In the near future, it will probably be entirely abandoned. This means that now is the best time to get those sweet, sweet vaporwave photos of capitalism gone awry.


Related Questions

What are people doing with dead and dying malls?

Many cities are now using the real estate of dead malls to create new office buildings and mixed-use real estate. Some are also converting the malls into affordable yet upscale apartment buildings. In some rarer cases, the malls are getting repurposed into large-scale medical buildings.


What is the Bridgewater Triangle?

The Bridgewater Triangle is a large area that is centered around Bridgewater, Massachusetts. It’s an area that is allegedly famous for having high levels of paranormal activity. Some claim that the area is cursed by settlements gone wrong, while others believe that UFOs are to blame. The area has been linked to strange shadows, weird lights in the sky, as well as the disappearances of hikers.It’s uncertain whether this triangle has any legitimacy behind it. However, it is a staple in both Connecticut and Massachusetts lore.


What are some of the best foods to eat while traveling in Connecticut?

Much like the rest of the Northeast, you can’t go wrong with eating some fresh seafood. White clam pizza, lobster rolls, and carpetbagger oysters are a good start. Many local sodas and root beers are also worth a shot. If you are a fan of savory foods, you can try out some steamed hamburgers or a “Bernice Original” cheeseburger.Long story short, expect flavorful New England food.

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Ossiana Tepfenhart
Ossiana Tepfenhart

Ossiana Tepfenhart is an expert writer, focusing on interior design and general home tips. Writing is her life, and it's what she does best. Her interests include art and real estate investments.

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