1860:

• During the Presidential Elections, Emmitsburg’s political views supported the Southern Democratic Party giving John C. Breckinridge 323 votes, more than half the population of Emmitsburg. 

• December of 1860, Emmitsburg resident Charles Donnelley is the first townsman to enlist in the Confederacy serving three years in Charleston, South Carolina in the 15th South Carolina Heavy Artillery. Charles Donnelley is one of nearly 500 Marylanders who traveled by ship to Charleston Harbor and witnessed the bombardment of Fort Sumter.

1861:

• During a meeting with the Maryland State General Assembly, Emmitsburg resident Doctor Andrew Annan was among those who attended gave Emmitsburg’s support to the preservation of the Union.

• Those Emmitsburg residents who had southern sympathies but did not make the trip to South Carolina began to head into Virginia and enlist into the service of the Confederacy.

• Most of the Emmitsburg men who fought for the Union enlisted into Company “C” of the 1st Potomac Home Brigade, Cole’s Cavalry. Company "C" was mustered into service at Frederick, Maryland on September 9, 1861.

• In November, during the special elections, many Union troops are sent to protect the voters at the Polling places.

1862:

• September 4th-7th, General Robert E. Lee's Confederate Army crosses the Potomac River and invades Maryland. His goals; liberate, recruit, re-supply, and if possible take the war into Pennsylvania.

• During the Maryland Campaign, on September 13th, Union General Alfred Pleasonton, whose headquarters was at Frederick, received an order from General McClellan to send a cavalry force to scout the Lewistown and Mechanicstown area and report any Confederate activity. As speculations of General Lee’s Army moving into Pennsylvania grew, a detachment of cavalry under Captain William Boyd made their way to Emmitsburg, arriving by nightfall.

• September 17th, the Daughters of Charity are petitioned by the state of Maryland to care for the wounded soldiers at Sharpsburg.

• October 11th, General JEB Stuart's Cavalry enters Emmitsburg during the 1st Chambersburg Raid just as Rush's Lancers were riding toward Gettysburg. During his raid Emmitsburg was occupied by Union forces under the command of Colonel Richard Rush and his Lancers.

1863:

• June 15th, General Robert E. Lee's advance of his Confederate Army enters Maryland and Pennsylvania.

A stable fire burns three-quarters of Emmitsburg. The first portions of the Union Army known as the Middle Department seize the mountain gaps upon South Mountain waiting for General Joseph Hooker's Army of the Potomac to take over possession.

• June 22nd, skirmish at Monterey Pass.

• June 27th, General Hooker's resignation is approved and General George Meade takes command of the Army of the Potomac. Newly promoted General George Armstrong Custer and a portion of his command encamp near the Tollgate at Saint Joseph's and hire Emmitsburg resident Jim McCullough as a guide.

• June 28th, skirmish at Fountain Dale. Members of Cole's Cavalry captures several artillerists on a foraging scout and bring them to Emmitsburg.

• June 29th, General John Reynolds orders the First and Eleventh Corps to march toward Emmitsburg from South Mountain, Middletown and Frederick around 4 a.m. and they will arrive at Emmitsburg around 6 p.m. General Reynolds sets his headquarters at Saint Joseph's Rectory and orders Signal Corps to Indian Lookout. First Corps encamps on the ground of Saint Joseph's. General Oliver O. Howard sets up his headquarters at Mount Saint Mary's and his Eleventh Corps encamps near Emmitsburg for the night.

With three comrades from his old company, Gwinn, Wolf and Crooks, Emmitsburg resident Samuel McNair started for Gettysburg and was the first Union soldier to enter Gettysburg after Ewell's Division moved North toward York. McNair captures a few Confederate soldiers, one of them carrying dispatches from General Lee to General Ewell. After making a reconnaissance of Lee's position, started to fall back to Gettysburg. After being spotted by Confederate soldiers, McNair and his party made a dash for safety. The rebel cavalrymen in hot pursuit, chasing them at a rapid rate towards Emmitsburg. Fortunately for the three intrepid soldiers at about the Peach Orchard, they met the advance of Buford’s Cavalry. It was this little band of Company C, Cole’s Cavalry that captured the first rebels on the famous battlefield of Gettysburg.

• June 30th, General Reynolds moves the First Corps to Marsh Creek and sets up his headquarters at the Moritz Tavern. He places the Brigades of Generals Stone and Biddle on picket between Emmitsburg and Gettysburg. On the evening of June 30th, through the morning hours of July 1st, the Third Corps under General Daniel Sickles was at Bridgeport, Maryland just east of Emmitsburg. Birney's Division of General Sickles' Third Corps was ordered to march to Emmitsburg and encamped at Saint Joseph's. General George Meade comes up with the Pipe Creek Defensive Line that stretches from Emmitsburg to Manchester.

• July 1st, General Sickles’ Third Corps marched from Bridgeport through Emmitsburg heading to Gettysburg between two and three o'clock that afternoon. Union engineers began surveying the land around Emmitsburg for a possible battle. For a few hours, the town of Emmitsburg was crucial to the war efforts. Preparing for the march, General Sickles took one brigade from his two divisions and two batteries and placed General Charles K. Graham in charge of the troops that General Sickles was keeping at Emmitsburg. General Sickles then sent a dispatch to General Meade stating he was taking his Corps forward to Gettysburg and that he had left two brigades of infantry and two batteries behind.

• July 2nd, more Federal soldiers came into Emmitsburg. These soldiers were the Army of the Potomac's U.S. Cavalry under the command of General Wesley Merrit. A dispatch came on July 2nd to move forward with the wagon train toward Emmitsburg, Maryland. With these orders General Merrit came into Emmitsburg and set up camp. Then the orders came for General Merrit to report to the battlefield on July 3rd.

• July 4th, a detachment of Confederate General Albert Jenkins' Cavalry Brigade enters Emmitsburg.

  Union General Judson Kilpatrick enters Emmitsburg being re-enforced there and heads toward Monterey Pass, where a major battle occurs that evening.

• July 5th, General JEB Stuart enters Emmitsburg after a brief skirmish near the modern day Emmit House. Stuart's Cavalry captures more than 70 Union prisoners and a few sutler stores. Among the prisoners are Alexander Gardner's staff that works for the Matthew Brady Photography Firm. Stuart leaves Emmitsburg after learning about the battle that erupted at Monterey Pass on South Mountain. Stuart heads towards Thurmont and then heads north back toward Emmitsburg after learning Harman's Pass on the Catoctin Mountain is occupied by Federal Cavalry. Cutting his way through Emmitsburg Gap, Stuart captures the Signal Corps at Indian Lookout.

• July 6th-7th, Union troops march past Emmitsburg trying to head Lee's retreating army off by way of Middletown to Hagerstown.

• July 7th, General Meade enters Emmitsburg and is hailed by Emmitsburg citizens.

1864:

• July 5th, Confederate General Early's Corps and General John C. Breckinridge's Division started to cross the Potomac River at Shepherdstown. As a precaution, Union Cavalry detachments patrol the area.

• July 9th, Battle of Monocacy.

• July 10th, Confederate Cavalry forages the area of Emmitsburg.

• July 14th, Union Colonel Clendenin's Cavalry moves toward Emmitsburg. The newly formed Second Delaware Cavalry under the command of Captain Milligan was to patrol the Middleburg area near Emmitsburg as part of their efforts to protect Baltimore.

• July 18th, Union forces began to patrol the Waynesboro area. General Lew Wallace sent Captain J. C. Hullinger, commanding a detachment of the 21st Pennsylvania Cavalry to march to Waynesboro via Emmitsburg.

• July 19th, Major General David Hunter received a dispatch from General D. N. Couch informing him that a few cavalrymen of his Department of Susquehanna had been scouting and fighting in Maryland. More cavalrymen were needed and ordered along the line near Greencastle, Waynesboro, and Emmitsburg.

• July 30th, A detachment of Hunter’s cavalrymen were ordered to march by South Mountain toward Emmitsburg. General Halleck sent another dispatch to General Hunter stating that Clendenin's Cavalry was ordered to scout toward Emmitsburg and send back information on the Confederate force that had entered Chambersburg. Meanwhile, General Lew Wallace sent a detachment of the 21st Pennsylvania Cavalry, under the command of Captain J. C. Hullinger to march to Waynesboro via Emmitsburg.

A signal camp was opened at Emmitsburg by Chief Signal Officer Amos M. Thayer relaying messages to the cavalry stationed at Emmitsburg as they waited. By that afternoon, a skirmish erupted at Emmitsburg as a repercussion from the burning of Chambersburg. A small contingent of Union cavalry guarding the area around Emmitsburg was driven into Emmitsburg by a superior number of Confederate forces.

• July 31st, Captain Franklin E. Town, Chief Signal Officer sent Lieutenant Ellis to Emmitsburg to communicate with Captain Thayer and ordered him to go to Chambersburg and report the operations of the enemy there. A line of communications was made along the Mason and Dixon Line that kept General Crook in communication with headquarters during his march toward Emmitsburg.

• August 1st, Lieutenant Ellis reported from High Rock that Chambersburg was burned.

• No more military activity was reported until the end of the Civil War.

1865: