Winsted-Lester Prairie Journal, October 27, 1997

The story of Robbers Cave
(Winsted, Conn.)


The Winsted Voice

Dedicated to Ralph Sears, a lovable, friendly man who enjoyed history and folklore.

No collection of folklore of an area called "the Town of Winchester" would be complete without acknowledging "Robbers Cave."

My first knowledge of the cave was from one of the neighborhood kids in the '30s. We were not gangs, yet every neighborhood had a group of kids who had fun together. In 1939, I was 11 years old, gullible, and inquisitive.

One day a group of older kids in the neighborhood were talking about a hike.

"Where are you going?" I asked.

"Robbers cave" was the answer.


"Sure," I said, and up the mountain we went, to the cave that to this day I visit from time to time.

Before long you would ask, "Hey, why do they call this place 'Robbers Cave?"

They answered, "Robbers, you know what robbers are, don't you? Robbers were here, hid out from the law, buried some money . . ."

And from that point on imagination took over, making up stories of the cave that filled the dreams and fantasies of a child's mind.

There are five basic routes to the cave, depending on where you lived in town. I lived on Charles St., so my route was to the eastern end of Rockwell St., up Mead's driveway at Highland Park, over the ridge to the cave, just below a wonderful lookout, easily seen today from Route 8 near the Connecticut Motor Vehicle Department.

At the time of the robbery, the view from the lookout included woods, old Route 8, the railroad line, Torringford St. and sections of Winsted. A second route to the cave was from Maple St., up the dirt road connecting with the dirt driveway to Mead's House.

A third route was up to the top of Pratt St., along the flat a few hundred feet, then taking the path to the left, just before Lookout Pleasure Park, to the lookout and cave.

Another route was down the trolley line at Highland Park a few hundred feet, then left on a path toward Winsted to a fork in the road- the trail to the right leads to the lookout pathway on the top of Pratt St.

The fifth route was down old Route 8, over the bridge, to the small stream that went under the read to Still River - following the stream that brought you to the cave.

The cave, located on the south side of what at the time was called an unfrequented mountain, can be described for modern folks as a two-story A-frame structure with three entrances. The lower floor had a private entrance, with a hallway leading to a small utility room. The main area had a large room with an opening to the southeast, with a side entrance for the kids.

The cave was named for the great robbery at the Winsted Bank in 1861. Somewhere between Friday night, Nov. 9 and Monday morning, Nov. 11, 1861, The Winsted Bank was robbed of upwards of $60,000 in gold, silver, bills of Winsted bank, bills and checks on Hurlbut Bank, miscellaneous bills, and Treasury notes.

The robbery was discovered on Monday morning at 9 o'clock by Mr. Gay, a teller. The robbers gained entry to Lawyer Gidding's office on the second floor, and cut the floor with the nicest care, allowing access to the vault eight and a half feet below.

The robbers covered the top of the vault with a large amount of ashes that were removed and banked up on the sides. The ashes served to deaden noise during the operation of gaining access to the vault. The top of the vault was a granite slab, eight inches thick and wide. A ratchet-drill was used to drill five three-inch holes in the slab, into which the gads (intermediate between a wedge and a drill ending in a point) were inserted.

Pieces of lead were placed on top of the gads, to deaden the sound, then hit with with a sledge hammer splitting the slab. Wooden wedges were used to raise the slab, allowing a chair to be attached. A jimmy and steel bar were used to move the slab out of the way, giving them access to the vault.

All the tools used in the robbery were left behind, including sharpened nails, thought to be used to pick the lock of the lawyer's office.

It took several nights to prepare for the final entry into the vault, so each night the wood floor, cut out, was replaced with care.

On Saturday, Nov. 10, entry into the vault was accomplished, giving them access to the prize. Good judgement was used, as only half of the Winsted Bank bills were taken, thus guaranteeing the bank would not fold and thereby render the bills useless.

The loot weighed close to 200 pounds, and was therefore fairly difficult to carry. Who did it? The Winsted Herald stated that for two weeks prior to the robbery, three men, strangers, had been seen frequenting the area of the cave that became known as Robbers Cave.

Hunters had seen the men, and their night fires seen from distant home sites. Upon investigation, remnants of their cooking, including utensils, were discovered in the cave.

The remains of a forge fire with bits of charcoal were found close by. Under a stone was a rubbercloth carpet bag containing a hand bellows, bits of charcoal, gads and wedges, plus a drill-step similar to one found in the bank. Many felt they would be able to recognize the three men should they see them again.

One writer stated that such ingenuity, such mechanical and financial acuteness combined, are acquired "only in some rogue's metropolis."

The bank offered a reward of $1,000. However, the only trace of the robbers was that three men were observed up at the turnpike gate between Winsted and Norfolk. They had carpetbags, apparently heavy, as they continually changed hands. This sighting was early Sunday morning. It was rumored that the robbers hid some silver in a stone wall, which was later recovered.

Richard Greenwald, identified by three different witnesses, was charged with the crime. Greenwald looked as innocent as a child, maintaining a tranquil mood listening to the charges against him.

I can find no records indicating that anyone was ever convicted or served time for this robbery. The following appeared in the Winsted Herald on Nov. 14, 1861: "A Hint: Burglars don't go about robbing banks in entire ignorance of the premises, the facilities, and the obstacles - Winsted Bank, take notice. Who, that knows the bank 'like a book,' has had access to every part of it, and consorts freely with the black-leg fraternity of New York? Look high and low, Messrs. Directors."

This statement supported my opinion that the facts indicate there was an inside man. Ralph Sears and I discussed calling on outside help to give us some answers. We thought the team of Lamont Cranston and Margo Lane could be of assistance. However, the weather turned cloudy leaving us without a "shadow."

I would have asked for an explanation for the following questions:

1. How were the three strangers, on foot, able to find a remote cave in an unfrequented mountain?

2. How were they able to have so much information and easy access to the bank area?

3. Why would men of this cunning and intelligence carry, on foot, this heavy load for miles when transportation was easily available?

For an explanation, consider the possibility that the following is true. The robbery is planned outside of town with blueprints of the bank and maps of the area. The robbers arrive in town aboard a night train, meet their accomplice and in the darkness go to the top of Pratt St..

In the early morning they find and move into the cave. The cave had been chosen for its remote location, with the robbers being able to move to and from the bank in the darkness of the night.

After the entry to the vault, the money is removed, placed on waiting horses, and held by an accomplice. They proceed west on the turnpike, dismount approximately one quarter mile from the tollgate, then walk through the gate for the purpose of identification, meeting their accomplice on the other side. The money is divided, with each man taking a predetermined direction to the final meeting at a later date. Have a nice day.

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