Celebrating 250: The 2DL Ambush at Poundridge

Disclaimer: Wix has been pushing to use their AI tools hard. Why I still keep my site on here is a mystery, but just so folks know, I won't ever use AI in anything I write. Not even to edit. I like hiring editors to actually edit my novels. And I like writing, so I always take the opportunity to improve my craft. AI does nothing for me in that regard.

Onward to the post:

The 2nd Light's ambush at Poundridge and Bedford, NY happened on July 1st, 1779, so we're a smidge 3-4 years early in celebrating the 250 of it, but since it's very hot and muggy here in the Northeast, and the weather will turn stormy later today - it is very appropriate to talk about the ambush and near destruction of the 2nd Continental Light Dragoons.

For those who have read up to Spymaster, the 2nd book in the 2DL series, you'll know that Tallmadge and the members of the 2DL face a lot of hardships and trials during 1777-1779. At this point in the war, it's a stalemate between the Continentals and the British. No one wants to move and smaller forces are sent out to try to both gain ground and to harass the enemy. Like the Southern campaigns, it's a war of attrition and its one that had a lot of the Westchester region and southern CT region burning due to raids. Most of the houses now built there that are considered historical and old are post-war houses. There are very few that are left due to the numerous raids happened upon by both sides.

In Tallmadge's own words regarding the ambush on July 1st, 1779:

At the commencement of this campaign, our regiment was ordered to its old station on the lines, below Bedford, North-castle, etc. Not long after we took the field, about July 1, 1779, Lord Rawdon with nearly all the British light horse, accompanied by a body of light infantry, made an attack upon our corps in the night. The onset was violent, and the conflict carried on principally with the broad sword, until the light infantry appeared upon our flanks, when Col. Sheldon found it necessary to retreat. This was done with so much celerity, that the enemy gained but little advantage. I lost in the affray a fine horse, most of my field baggage, and twenty guineas in cash, which were taken in my valise with my horse.

In Tallmadge's memoir, he tends to understate his role in certain campaigns and areas - especially when his spycraft is involved. There is pride in his work, but after many, many years removed from the American Revolution, Tallmadge is still quietly proud, but does not want the credit for spycraft - which is very much still aligned with the norms of the day. (It's only after the Civil War that spycraft starts to gain a bit of prominence - and Nathan Hale is celebrated as Connecticut's official state hero.) Thankfully, Tallmadge's actual letters (to General Heath) along with those from Sheldon (to Washington) and Banastre Tarleton's memoirs, do provide a better picture of what happened.

Repainting the picture of Bedford, Poundridge and North Castle area of NY. It is hilly; contrary to what many might think of southern CT and coast NY/Westchester area. It is not like LA/West Coast version of hills, but rather it is considered soft rolling hills. Occasionally steep and uneven. You can curve and go straight down into a river or brook and then suddenly have to go 30 degrees or more to the bank to get up to the top. 100 feet, but a fast climb.

Even today, driving along the Merritt Parkway and Hutchison River Parkway (Route 15), one can see hills, curves (hooray for driving at 15 past the speed limit), and still need to be extra careful, especially at night. There are no lights so one can easily imagine what it was like back in Colonial America. The density of woods were also factors. There were farmland, but they were limited, so the woods were dense enough to hide troops within or conceal the movement to a certain degree. This is both true back in Colonial America and also in modern times. Less farmland than houses nestled among the acreage and copse of woods. Money buys a lot of privacy when it comes to trees and density in the modern day.

Tallmadge knew these types of woods were not great for scouting, so he resorted to his tactics of 1777, to randomize patrols, randomize the location of the troops he was commanding. Anything to throw off the patrolling British so that they would not be ambushed. Sheldon eventually joined with the regiment (he was detached to settle his late father's affairs) around late June. Still getting familiar with the area, he did not heed Tallmadge's warnings and even a credible report from a local spy (Kennicott) that something felt off when heavy rain started to fall the night of July 1st. In ways, Sheldon was right - no one could fire a single musket with that much rain. But, Tallmadge knew that muskets need not be fired for them to be ambushed.

And this was because of the 3DL's destruction the previous year. Caught off guard and taken with cold steel. Tallmadge was perhaps paranoid, but for good reason. He knew who was operating in the area and they were the same officers that killed his fellow spymaster, Major Clough and severely wounded the commanding officer of the 3DL - Col. Baylor. And like the 2DL, they had been operating exactly like they had - except in New Jersey. They even had a similar make up - an unfulfilled position of a field officer, a Lt. Col.

Due to the curvature of the hills and the roads that winded around the woods, Tallmadge and the others who had started a morning patrol from a vedette alert, were nearly ambushed by Tarleton and Rawdon's incoming forces. Then, what you read in the novel is all but true except for one little thing.

Tallmadge never got injured.

The "fiction" aspect of historical fiction and the 2DL's fight at Poundridge and Bedford:

Call it a bit of Hollywood flare in my part, or because I wanted characters to react a little more believably if someone got injured while fleeing such a chase, I ended up giving a flesh wound to Tallmadge. His shot in the shoulder is more of a deep graze than actual ball going through him - a musket ball would have shattered the whole of the bone and shoulder, which would have left Tallmadge far more severely injured. I left it somewhat questionable since he was wearing his uniform and riding. He's more shocked and surprised than actually injured and recovers after they've rallied several miles down to chase their pursuers back and away.

Also - I like showing affection to my favorite characters by injuring them. Don't ask. It's something a lot of writers like to do - put their characters through hell to see who they are on the other side.

The aftermath and back to reality (and not fiction):

Tallmadge's horse did get captured as did his valise and he lost some valuable intelligence. Higday was compromised as an agent that he was planning to use via Washington, but the man managed to burn incriminating documents before the British found him. There is a chance this was where the British found out about the mysterious Culper that was in communication regarding troop movements of New York, but no source I've found ever confirmed that. There are a few other incidents that might have alerted the British to Culper, but even those are questionable.

Now to wait out tonight's thunderstorms and the muggy heat. Actual July 1st, 2026 humidity, heat advisories and thank you for modern conveniences of AC. I'd hate to be the 2DL in this weather, patrolling and not even getting to rest much in whatever little shade they had.