During the outbreak of the Civil War Woodsboro, Maryland was mainly sympathetic to the Union cause. Several men from Woodsboro joined many of the Union units including the 7th Maryland Infantry. Abraham Dern who grew up in Woodsboro, joined Company A of Cole's Cavalry and returned home after the war's close. On November 14, 1861, for protection of loyal Union men at the polls of the late election, Major Stone served as the provost Marshall of Woodsboro and a few other election precincts. Because Maryland was so divided in it's political views, no armed men went near the polls.

In October of 1862, Confederate General JEB Stuart and his cavalry made their way across the Potomac. Their objective was to capture the Union depots at Chambersburg, Pennsylvania. After completing his objective, General Stuart led his men back toward Hagerstown when he realized that a portion of Union Cavalry is following him. General Stuart orders his men to march toward Gettysburg. After passing through Cashtown, General Stuart decides to travel to Fairfield and make his way to Emmitsburg, Maryland. Just one hour before the Confederate arrival in Emmitsburg, 140 men of the 6th Pennsylvania Cavalry known as Colonel Rush's Lancers had passed through the town. A courier was captured carrying dispatch to Colonel Rush notifying him that 800 Cavalrymen under Union General Pleasonton was in pursuit of Stuart's Cavalry.

At a half past 10 p.m. on the night of October 11th, a company of the 6th Pennsylvania Cavalry observed General Stuart's column marching through Woodsboro. Corporal John Anders of Company D, Rush's Lancers gallantly scouted the Confederates at Woodsboro. He dismounted and entered Woodsboro on foot. He talked freely to the men of Stuart's Cavalry until he was detained for suspicion of being a Union Loyalist. Corporal Anders managed to escape and rejoined his unit shortly after midnight. Two prisoners that were taken at Fairfield, Pennsylvania by the names of Hartman and Sheads made their escape at Woodsboro, Md.

Before the battle of Gettysburg, on June 29th, 1863, marching orders at 4 a.m. were carried out. Portions of the Union Army would march through Woodsboro on their way to Middleburg. The 12th Corps and the 3rd Corps along with their corresponding Artillery would march through Woodsboro followed by General Meade's Headquarters wagon train. General Farnsworth's Brigade of Cavalry also traveled through Woodsboro as they headed toward Taneytown.

Union General Slocum commanding the 12th Corps wrote to General Meade at Woodsboro about delays occurring with the Union wagon trains upon Woodsboro Pike. Because of the wagon situation, this was slowing his Corps and they would not make it to Middleburg on time and would be forced to encamp at the double Pipe Creek near the Frederick and Carroll County line. Colonel Warren Packer commanding the 5th Connecticut Volunteers also encamped for the night at Woodsboro.

After the battle of Gettysburg, Woodsboro witnessed many of the same troops marching to Frederick, trying to get in front of General Robert E. Lee's Confederate Army. On July 7th, the 12th Corps and 2nd Corps marched through Woodsboro on their way to Frederick. Many officers were impressed with the beauty of Woodsboro and how well were the condition of the roads. At 8 p.m. the Artillery reserve was ordered to encamp at Woodsboro and would resume their march to Frederick early in the morning of July 8th.

In June of 1864, Confederate General Robert E. Lee sent a corps of men under the command of General Jubal Early northward from Petersburg, Virginia to conduct a campaign that would threaten Washington. Many Maryland towns would see troops from both sides come through their towns much as they did during the Gettysburg Campaign a year earlier. Woodsboro was not exception. On July 9th, 1864 during the battle of Monocacy, the Chairman of Executive Committee David Willis reported that Confederate Cavalry had scouting parties at Woodsboro and were reported stealing horses and robbing stores.

Today, Woodsboro still holds the same appearance as it did during the Civil War. Although Woodsboro has grown over the past decade, the modern day convinces and the quarry has not taken any of the historical aspects on Main Street. Woodsboro is located on modern day Route 194 where it connects to modern day Route 550.