General Sheridan and the amusing incident at the Toll Booth

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southern blue

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General Sheridan was in hot pursuit of Confederate General Jubal Early after the Battle of Third Winchester. He followed Early down the Valley Pike to the outskirts of Winchester only to be met with fierce resistance. No it was not Confederate Soldiers making a brave stand...it was instead the keeper of a toll both. Charlotte Hillman refuse to raise 'the pike' to allow General Sheridan and his armies through. If he wanted through he had to pay the toll like everyone else. Sheridan pledged that he and his officers would pay later but he could not 'vouch for all of his men'. Hillman raised the pike and allowed them through making a notch on the pike for every ten soldiers who passed through. After the war a bill was sent to Washington and it was paid.

Considering how many men Sheridan had with him that must have come to a substantial sum.

toll%20house%201_zpsywvqfmf8.jpg


The toll house was still standing as late as the early 1960s. Facing the picture it is to the immediate right of the garage.

toll%20house_zpstht6ozgj.jpg



The house was taken down before The Preservation of Historic Winchester was formed. The area today....its the corner of Route 11 and Cedar Creek Grade if anyone is interested.


Expired Image Removed
 
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southern blue

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I've read that story before and I was a bit surprised that the bill had actually been paid, to be honest.

Rebecca
I suppose it would depend on how it was presented. A random toll bill without explanation probably would have been paid although I would wonder if someone had to contact Sheridan about this. "What's this about a toll both outside of Winchester charging us XX dollars?"
 
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southern blue

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If Sheridan would march on a single road he would at this time have more than 35.000 combatants alone ... must have been pretty small notches to get thousands of them on that pike.
There were several roads out of town so all of them wouldn't travel on this one alone.
 

kholland

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Great story! It reminds me of the scene from the Mel Brooks' movie"Blazing Saddles" where Hedley Lemarr' s" rustlers, cut throats, murderers, bounty hunters, desperados, mugs, pugs, thugs, nitwits, halfwits, dimwits, vipers, snipers, con men, Indian agents, Mexican bandits, muggers, buggerers, bushwhackers, hornswogglers, horse thieves, bull dykes, train robbers, bank robbers ...." were held up by the tollbooth in the middle of nowhere.
 

Pat Answer

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Great story! It reminds me of the scene from the Mel Brooks' movie"Blazing Saddles" where Hedley Lemarr' s" rustlers, cut throats, murderers, bounty hunters, desperados, mugs, pugs, thugs, nitwits, halfwits, dimwits, vipers, snipers, con men, Indian agents, Mexican bandits, muggers, buggerers, bushwhackers, hornswogglers, horse thieves, bull dykes, train robbers, bank robbers ...." were held up by the tollbooth in the middle of nowhere.
:bounce: That very scene popped into my mind as I read the OP.

Is there a source for the story? I wonder if the bill is preserved in an archive somewhere...
 
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southern blue

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:bounce: That very scene popped into my mind as I read the OP.

Is there a source for the story? I wonder if the bill is preserved in an archive somewhere...
Charlotte Hillman was a real person and the toll booth was called the Hillman Toll House.

The earliest record I can find is from 'The Winchester News Dec 29 1908.

For whatever reason the link to this shows up on my Kindle tablet and not on my PC (probably because of the difference in the browsers) but you can see a copy at the Library of Congress Chronicling American-The Winchester News-Dec 29 1908.
 
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Great story indeed. I wonder if it's true? This Hotchkiss map from 1862 shows the toll-gate which was at the intersection of the Pike and the Cedar Creek Turnpike (aka Cedar Creek Grade).

battle-winchester-map.gif


Sheridan's memoirs clarify who was on what road and confirm that Merritt rode down the Valley pike while the infantry marched in the open country to either side:
"The night of the 19th of September I gave orders for following Early up the valley next morning — the pursuit to begin at daybreak — and in obedience to these directions Torbert moved Averell out on the Back road leading to Cedar Creek, and Merritt up the Valley pike toward Strasburg, while Wilson was directed on Front Royal by way of Stevensburg. Merritt's division was followed by the infantry, Emory's and Wright's columns marching abreast in the open country to the right and left of the pike, and Crook's immediately behind them. The enemy having kept up his retreat at night, presented no opposition whatever until the cavalry discovered him posted at Fisher's Hill"

According to the 1908 publication Shenandoah Valley Pioneers and Their Descendants: A History of Frederick County by Thomas Kemp Cartmell, Mrs. Hillman collected tolls from Jackson and Banks as well!

It appears to be "local tradition" and that is usually worth the paper it's written on. Is there a reliable source for this tale?
 

southern blue

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It appears to be "local tradition" and that is usually worth the paper it's written on. Is there a reliable source for this tale?
So far I haven't been able to find any contemporary accounts. The article in my post above is the earliest I can find at the moment. However Mrs. Hillman did run the Toll Both and given the attitude of the Winchester women toward the Yankees during the war I can see no reasons for it not to be true at this time.
 
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http://chroniclingamerica.loc.gov/lccn/sn86069133/1908-12-29/ed-1/seq-7/#date1=12/29/1908&index=0&date2=12/29/1908&searchType=advanced&language=&sequence=0&lccn=sn86069133&words=Sheridan&proxdistance=5&rows=20&ortext=&proxtext=&phrasetext=sheridan&andtext=&dateFilterType=range&page=1

The link to the December 1908 newspaper article from the Winchester News (from Lexington, Kentucky, not Va.). It makes fascinating reading although the details differ from other versions. In this one, she's pretty and Sheridan is beguiled into paying his own toll while each of his officers pay for theirs.

That there was a toll booth and a Mrs Hillman is not doubted. But the lack of any source prior to 1908 and the description elsewhere of this being "local tradition" are sufficient reason to not believe the story pending a reason to do so. The story proposes that Sheridan and his officers were travelling in front of his entire army - which is highly unlikely. That Sheridan doesn't mention it (and he loved to relate stories about pretty ladies) is strike two. And the fact that Merritt's men had all passed before Sheridan seems clear. Plus his infantry was not on the turnpike but on either side of it (according to Sheridan's account). And given the Federal government's outright refusals to pay compensation to Southerners for almost anything after the war, that they would pay a hostile rebel woman a toll based on several thousand soldiers marching in pursuit of the enemy is also suspect.

In its favour - Sheridan was a pompous *** and just the sort to think that tossing a few coins to an obdurate rebel was amusing. But that's why his silence on the matter is kind of weird.

I'd love it to be true though. What do we make of the other 1908 story that she demanded tolls from both Jackson and Banks in the earlier Valley Campaigns?
 

southern blue

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I looked through some history books that I have on Winchester and found no mention of the incident. One is a straight history and the other is the history told through diarists. The diarists didn't not mention it either but then several of them were not here at the time. They either left or were driven out. The one Unionist diarist barely mentions Third Winchester at all which I found a bit odd....but then the town was almost immediately overwhelmed by wounded.

Did find Hillman's tombstone. She is buried in Mount Hebron Cemetery in Winchester and according to that she was 60 years old at the time of the war (which actually jives with the local accounts that she was a mature woman. I was a bit surprised when I saw the 'young and pretty' thing; I had never heard her described that way).

I did come across someone whose family owned the garage in the 1950s picture. He was very matter of fact that yes that was the toll house where Charlotte Hillman demanded Sheridan pay the toll. Like most though he doesn't know where the story started It was just always...there and accepted sort of like the story of General Jackson pulling train locomotives by horse power up the Valley pike from Martinsburg to Strasburg but that's another thread.

I might go spend some time in the archives at Handley library in Winchester and see what they have.
 

M E Wolf

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It isn't the only incident of troops having to pay tolls.

O.R.--SERIES I--VOLUME XLIX/1 [S# 103]
FEBRUARY 15-16, 1865.--Scout from Nashville, on the Nolensville Pike, Tenn.
Report of Capt. Robert H. Clinton, Tenth Tennessee Infantry.
NASHVILLE, TENN., February 17, 1865.
MAJOR: I have the honor to report that, in obedience to orders received from Major-General Rousseau, on the 15th of February, at 11 a.m., I proceeded with a force of thirty men (Captain Poston's company, Fourteenth Tennessee Cavalry), on the Nolensville pike, in search of certain guerrillas who were committing depredations on and in the vicinity of that road. Some ten miles from town I received information from citizens coming into market that there were three bushwhackers at the next toll-gate, which was fourteen miles from the city. Having heard while out on a scout a few days previous that they were in the habit of resorting to this toll-gate, and knowing the impossibility of reaching it without being seen at some distance, I used the expedient of pressing two country wagons, dismounting eight men, and placing four in each wagon, I getting into the foremost one; then pulling the covers close down so as to entirely conceal the men, I ordered the foremost wagon to drive up to the gate as though he was going to pay toll. I had previously given orders to the men not to fire unless they were fired upon or unless they could not halt any one who would run away from the house. As soon as the wagon halted two men came to the door and I sprang up. One of the men in a very rough manner asked me, "What do you want here?" I asked him who he was. In reply he told me that I could not come into the house, and immediately ran into the house, slamming the door after him. I jumped out of the wagon and ran to the door, forcing it open and calling to him to halt and not run or he would be shot, but before I could force the door and get through the house he had made his way out into the back yard and was running off through the corn-field. The men halted him several times, but he paid no attention to them. By the time I reached the back yard the men fired on him, and, I am sorry to say, killed him. I do not think, taking all the circumstances into consideration, that the command can be blamed for his death, for the innocent are brave as a lion, but the guilty flee from their shadow. Be that as it may, his death was a circumstance to be regretted, and no one regrets it more than I do, and an article published in this morning's Dispatch, stating that his life was threatened by one of the men, is entirely false and without foundation, as is, in fact, the whole article published by that paper in regard to the scout and its proceedings.

[extensive excerpt]
I have the honor to be, very respectfully, your obedient servant,
R. H. CLINTON,
Captain, Tenth Tennessee Infantry.
Major POLK,
Assistant Adjutant-General, District of Tennessee.
----------
O.R.--SERIES I--VOLUME XLIII/1 [S# 90]
UNION CORRESPONDENCE, ORDERS, AND RETURNS RELATING SPECIALLY TO OPERATIONS IN NORTHERN VIRGINIA, WEST VIRGINIA, MARYLAND, AND PENNSYLVANIA, AUGUST 4, 1864, TO AUGUST 31, 1864.(*)--#

HEADQUARTERS CAVALRY CORPS,
August 11, 1864--10.45 a.m.
General MERRITT:
I do not think it best to go beyond the Front Royal pike, for there is a good force of infantry in front of Custer, and they would move down and cut you off. If possible occupy the pike and send up a party toward Winchester, and if they can get about three [miles] from the Double toll-gate, it might warrant sending a small party toward Newtown. Send me back now about every fifteen minutes how things are going. There is firing with Custer, but he has sent no report. I have directed him not to engage their infantry till I can hear from you.
Yours, &c.,
A. T. A. TORBERT,
Brigadier-General and Chief of Cavalry.
--------------
O.R.--SERIES I--VOLUME XLIII/1 [S# 90]
UNION CORRESPONDENCE, ORDERS, AND RETURNS RELATING SPECIALLY TO OPERATIONS IN NORTHERN VIRGINIA, WEST VIRGINIA, MARYLAND, AND PENNSYLVANIA, AUGUST 4, 1864, TO AUGUST 31, 1864.(*)--#
HEADQUARTERS TH1RD CAVALRY DIVISION,
August 30, 1864--6 p.m.
Brigadier-General MCINTOSH,
Commanding First Brigade:
General Torbert wishes you to send one good squadron on the Berryville-Winchester pike, as near to the Opequon Creek as you can. Instruct the officer that is detached to move rapidly, and if he meets any parties of the enemy to endeavor to take prisoners; information is wanted. A woman at the toll-gate just this side of the Opequon will give any news she may possess.
Very respectfully, your obedient servant,
J. H. WILSON,
Brigadier-General.
-----
continued
 
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M E Wolf

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O.R.--SERIES I--VOLUME XLIII/1 [S# 90]
AUGUST 7-NOVEMBER 28, 1864.--The Shenandoah Valley Campaign.
No. 2.--Itinerary of the U.S. Forces commanded by Maj. Gen. Philip H. Sheridan.(*)

Cavalry:
First Division.
August 1 to 6.--The division was engaged in embarkation from City Point, Va., to Giesborough Point, D. C., and completed on the 7th.
August 7.--Marched, via Washington, to Tennallytown. <ar90_90>
August 8.--Marched to Poolesville, Md.
August, 9.--Marched to Harper's Ferry.
August 10.--Marched via Charlestown and Berryville, skirmishing with the enemy at Stone Chapel.
August 11.--Engaged the enemy's cavalry near Winchester and drove them from toll-gate, and fought his infantry at Newtown.
August 12.--Marched to Cedar Creek.
August 13 to 15.--In position at Cedar Creek.
August 16.--Marched to Cedarville, routed the enemy's cavalry and infantry, taking 300 prisoners and 2 stand of colors.
August 17.--Marched to Berryville.
August 18 to 20.--Encamped at Berryville, frequently skirmishing with the enemy's cavalry.
August 21.--Marched to Charlestown; continued skirmishing.
August 22.--Marched to Shepherdstown.
August 23 and 24.--Encamped at Shepherdstown.
August 25.--Made a reconnaissance in force to Kearneysville; heavily engaged throughout the day; encamped near Halltown.
August 26 and 27.--In camp.
August 28.--Marched via Leetown; drove the enemy's cavalry through Smith field to Bunker Hill; encamped at Smithfield.
August 29.--Engaged the enemy's infantry, artillery, &c.
August 30.--Marched to Berryville, and encamped at Berryville on the night of August 31, 1864.
September 1.--The division was encamped near Berryville.
September 2.--Marched to Rippon and back to Berryville again.
September 3.--Marched to White Post.
September 4.--Returned to Berryville and skirmished with the enemy.
September 5.--Moved to Summit Point and took position on the right of army, where it remained from the 6th to the 14th engaged in picketing and scouting, frequently skirmishing with the enemy.
September 15.--Engaged and drove the enemy across Opequon Creek at Seivers' Ford, capturing a number of prisoners.
September 16 to 18.--In camp.
September 19.--Engaged in the battle of Winchester, capturing 2
pieces of artillery, 800 prisoners, and 5 stand of colors.
September 20.--Marched to Strasburg.
September 21.--Marched to Front Royal.
September 22.--Marched to Milford; skirmished with the enemy.
September 23.--Marched to Cedarville via Front Royal, repulsing, with severe loss, an attack of partisan cavalry.
September 24.--Routed enemy's cavalry at Luray Court-House, capturing 80 prisoners and 1 stand of colors.
September 25.--Marched to Harrisonburg via New Market.
September 26.--Marched to Port Republic, pressing enemy's rear toward Brown's Gap.
September 27.--Marched to Cross Keys.
[end of excerpt]
 

M E Wolf

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This may also be related:

O.R.--SERIES I--VOLUME XLIII/1 [S# 90]
AUGUST 7-NOVEMBER 28, 1864.--The Shenandoah Valley Campaign.
No. 35.--Report of Maj. Robert Munroe, One hundred and thirty-ninth Pennsylvania Infantry, of operations September 19.
HEADQUARTERS 139TH PENNSYLVANIA VOLUNTEERS,
September 21, 1864.
SIR: I have the honor to forward the following report of the operations of my regiment on the 19th instant:
At 1.30 a.m. of the morning of the 19th instant we broke camp near Clifton, and, after a short delay, started off toward the Winchester pike, my regiment being the advance of the brigade. After reaching the pike the direction of the march was changed toward Winchester. After having advanced about two miles beyond the Opequon Creek we formed line of battle to the left of the pike, the One hundred and thirty-ninth on the extreme left of the brigade, the left of the regiment resting on the side of a small hill, a ravine between us and the Third Brigade, and a dense growth of small timber in our front. The rebels had two guns but a short distance from our front, with which they annoyed us considerably, but did not do a great deal of damage. Having received orders, I advanced a skirmish line through the wood to the field in front. In the charge of Lieutenant Crawford, of Company E, they held the position until the line of battle advanced, when they rejoined the regiment. About noon the whole line advanced. It was very difficult for us to get through the woods on account of its density, but after we were clear of the timber the line was formed in good order and advanced on the double-quick under a very heavy fire of shell and musketry from the enemy. The enemy gave way precipitately before us and fell back to the second woods. Here they endeavored to make a stand, but only for a moment, as I threw some skirmishers into the woods from the left of the regiment, and with the balance advanced on the right of the woods to a road in the ravine, which runs in an oblique direction with our line of battle. Down this road the rebels were fleeing in the greatest confusion to a field beyond our left flank. Part of the regiment pursued, capturing a good many prisoners, until I ordered them to return, fearing that they would be separated to a great distance from the balance of the line and in turn be captured themselves. Although the men were very much exhausted with the heat and fatigue, yet still the line advanced; the rebels retreating, very much disorganized. We continued our charge for a distance of at least 800 yards, and halted on a by-road running nearly parallel with our line of battle; here we commenced firing on the rebels, who were forming in our front and had already established batteries which commanded our line. Soon we ascertained that the troops on our right had fallen back, and under the direction of Captain Lyon, of General Wheaton's staff, we changed the direction of our line more to the right, and made preparations to give the rebels a brisk reception. However, as we now had but few troops on our right and no connection on our left, it was deemed more prudent to fall back, which we did after receiving orders from Captain Lyon and Captain Eckman, of the brigade staff, and formed on the left of the Ninety-third Regiment, which, with the other regiments of the brigade, were in line on a road running parallel with the road which we had just vacated. The regiment remained in line on said road for about two hours or more, apparently waiting for the Nineteenth Corps to re-establish their lines, which had been somewhat con fused in the charge. At last the order was given to forward, which the regiment and brigade did with alacrity and in good order. We had advanced but a short distance when we encountered the fire of the enemy, and several of the regiment were wounded. The regiment was particularly annoyed by a battery of the enemy posted on their left flank and also by the rebel infantry, who were posted in a point of woods on their left. We advanced to the house on the right of the pike, where we halted and commenced firing. After a short time the right of our lines advanced, the enemy retiring, when we again advanced and halted at the toll-gate, where we remained until we were ordered to bivouac.
Very respectfully, your obedient servant,
ROBERT MUNROE,
Major, Commanding Regiment.
Capt. GEORGE CLENDENIN, Jr.,
Assistant Adjutant-General.
 

M E Wolf

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May be connected...

O.R.--SERIES I--VOLUME XLIII/1 [S# 90]
AUGUST 7-NOVEMBER 28, 1864.--The Shenandoah Valley Campaign.
No. 74.--Journal of Capt. Jed. Hotchkiss, Topographical Engineer, Second Corps, Army of Northern Virginia (Valley District), of operations August 4-December 31.(*)
[extensive excerpt]

Thursday, August 11.--Appearances indicating a general attack by a large force, we this morning formed a line of battle covering the approaches east and southeast of Winchester; Breckinridge covering the Berryville and Millwood roads, Ramseur the Front Royal road, and Rodes the Martinsburg road. Everything was moved from Winchester and we had a skirmish on the Millwood road. About noon I guided Gordon across the country, by a route I had selected in the a.m., to the pike near Kernstown and took him to a position south of Newtown. The rest of the army followed, and we had a brisk skirmish, about dark, on the road to the Double Toll-Gate from Newtown. We drove the enemy back and encamped near Newtown. Headquarters at Chris-man's. Very warm. Bryan's and Lowry's batteries, on the Millwood road, were engaged some.

[extensive excerpt]
 
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KansasFreestater

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Great story! It reminds me of the scene from the Mel Brooks' movie"Blazing Saddles" where Hedley Lemarr' s" rustlers, cut throats, murderers, bounty hunters, desperados, mugs, pugs, thugs, nitwits, halfwits, dimwits, vipers, snipers, con men, Indian agents, Mexican bandits, muggers, buggerers, bushwhackers, hornswogglers, horse thieves, bull dykes, train robbers, bank robbers ...." were held up by the tollbooth in the middle of nowhere.
First thing I thought of too!!
 
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cash

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Great story! It reminds me of the scene from the Mel Brooks' movie"Blazing Saddles" where Hedley Lemarr' s" rustlers, cut throats, murderers, bounty hunters, desperados, mugs, pugs, thugs, nitwits, halfwits, dimwits, vipers, snipers, con men, Indian agents, Mexican bandits, muggers, buggerers, bushwhackers, hornswogglers, horse thieves, bull dykes, train robbers, bank robbers ...." were held up by the tollbooth in the middle of nowhere.
Somebody's gonna haff ta go back 'n git a s___ load a dimes.
 
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