An Overview of the Battle of Monterey Pass

On the evening of July 4th, 1863, one of the most confusing battles of the Civil War occurred during the retreat from Gettysburg known as the battle of Monterey Pass. Around 9:00 p.m. on South Mountain, the Union cavalry under the command of General Judson Kilpatrick came in contact with the Confederate 1st Maryland Cavalry under Captain George Emack, who had a small detail guarding the approach to Monterey Pass, re-enforced by one cannon from Captain William Tanner’s Battery.

Darkness set in during a blinding rainstorm. The Confederate artillerists, wearing gum blankets to protect them from the elements of the weather, opened fire on the head of Kilpatrick’s advance. As the confusion subsided, the Confederate cavalrymen charged, pushing the Kilpatrick back until they reached the Federal artillery that was positioned near Fountain Dale.

For several hours, during the blinding thunderstorm in the middle of the night, the battle was carried out in between lightning strikes and muzzle flashes. Six hours of heavy fighting had spilled over to Fairfield Gap as well as Leitersburg while General Kilpatrick gained the South Mountain summit of Monterey Pass. At Fairfield Gap, a portion of the 1st Michigan Cavalry was beaten back by Confederate cavalry while at the Monterey House, two guns of Pennington’s battery began shelling the Confederate wagons.

By 3:30 a.m. on July 5th, Kilpatrick successfully reached the turnpike where Ewell’s wagon train was located, capturing and destroying 9 miles worth of wagons, taking 1,360 prisoners and a large number of horses and mules as they moved on toward Ringgold, Maryland.

Monterey Pass is the second largest battle that occurred in Pennsylvania and was the only battle ever fought on both sides of the Mason and Dixon Line, taking place in four counties, Frederick and Washington Counties, Maryland and Adams and Franklin Counties, Pennsylvania. Monterey Pass is situated on the South Mountain range and being a direct route to the Potomac River, it was used by the bulk of the Confederate Army during it’s withdraw from Gettysburg.

8 thoughts on “An Overview of the Battle of Monterey Pass

  1. Anonymous August 23, 2010 / 5:21 pm

    John, Thanks for the great information on this Battle. I was up there over the past weekend looking over the ground and trying to orient myself to the terrain and what happened there. I love the picture in your article. Do you know the time it was taken and can you specify any detail on what I'm looking at? If I had to guess, I'm thinking we're looking westward thru the Pass, with Mount Dunlop on the left? Probably a poor guess.Thanks again,Jeff Whiting

  2. By John A. Miller August 23, 2010 / 7:23 pm

    The photograph was taken in the 1870's early 1880's just after the Western Maryland Railroad came through South Mountain. This photograph is looking toward Fairfield and Fairfield Gap is located in the so called humped. The photograph was taken from where the Clermont was located about 100 yards from the modern day Hawley Memorial Church.

  3. Anonymous August 23, 2010 / 8:23 pm

    John, Thanks for the clarification. So, if I understand you correctly, we're looking at the equivalent of the modern fork in the roads where Furnace Rd peels off northward from the Old Waynesboro Pike (Charmian Rd)? Very neat. I really like to try to get some idea of how it really was there, 150 years ago. It's difficult w/ all the development.Thanks again,Jeff Whiting

  4. By John A. Miller August 23, 2010 / 9:14 pm

    Jeff, you are correct on the location. The development actualy for the most part happened during the Resort Era (1870-1920) when the Western Md RR came through and copper was discovered. Most of those houses you see are on the Register of Historic Places. Thank you for the interests. I will start posting more Monterey Pass related items here in a few weeks.

  5. Anonymous August 23, 2010 / 9:52 pm

    John, Thank you for your work. I was prompted to get to Monterey Pass after attending your talk "War Returns to South Mountain" the previous weekend. I'm looking forward to whatever and all info you might come up with.Thanks again,Jeff

  6. By John A. Miller August 23, 2010 / 10:19 pm

    Jeff,I remember you and glad to see that someone in my group took an interest to seek the subject even further. If I can be of any assistance, please let me know until then, please enjoy the War Returns to South Mountain Blog. Keep an eye out for any events that Monterey Pass or South Mountain Battlefields decide to do as this is a great time to learn about the CW history of the region.

  7. Carson Collins October 28, 2015 / 12:39 pm

    Hi John,
    My boss, Tim Noonan over at Heritage Histories, is writing a family history for a client and would like permission to use the image of Monterey Pass you have in this post for the book.
    If you could contact me and let me know what we need to do to obtain permission, that’d be great.
    Thank you,

    • John A. Miller October 29, 2015 / 2:36 pm

      I would give credit to the Antietam Watershed Association or John McClellan.

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