The Shenandoah Valley was an "avenue of invasion" to both Union and Confederate armies. It also was the "Breadbasket of the Confederacy," and as such was a prize to be captured by the Union Army, so fighting raged up and down the Valley's length from the beginning of the war. However, it was not until 1864 that Long Meadow saw fighting.
Following his victories at the battles of Third Winchester and Fisher's Hill in September and October, 1864, Union Ma. Gen. Philip Sheridan and his 32,000 man Army of the Shenandoah conducted a systematic destruction of a 75 mile swath of the Shenandoah Valley. "The Burning" essentially laid waste to the Valley's vast agricultural resources. Thinking the Valley campaign was over, Sheridan camped his army along Cedar Creek and in the fields around Belle Grove.
The Confederate Army of the Valley, commanded by Lt. Gen. Jubal Early, shadowed Sheridan's movements and camped his troops south of Strasburg, five miles to the south. On October 17, Confederate Maj. Gen. John B. Gordon and several other topographical engineers hiked to Signal Knob, at the north end of the Massanutten. There Gordon could see "every road and habitation and hill and stream for miles in every direction. Sheridan's entire army as well as every piece of artillery, every wagon and tent and supporting lines of troops" was clearly visible.
From that vantage point, the plan for the Battle of Cedar Creek was conceived. It was to be a surprise attack from around the base of the mountain to the left of the Union line, its weakest point. From Signal Knob, Gordon saw Long Meadow and figured the army could turn left at the house and use Long Meadow Road as a direct route to the Union left, held by the 8th Corps.
The Confederates left Strasburg under cover of darkness at about 8:00 p.m. on Oct. 18 and crossed the North Fork of the Shenandoah River in two places. Divisions under Gen. Stephen Dodson Ramsuer (who was killed later that day) and Gen. John Pegram met Gordon and his division at Long Meadow and marched quietly along the road to their attack positions. When the first Confederate shots were fired in dense fog at about 4:30 a.m., the Union encampments were taken completely by surprise and by 10:30 that morning had been routed to a mile north of Middletown.
Unfortunately for the Confederate Army, Early decided to let his exhausted and starving troops stop to rest and eat the food the northerners had left behind. Sheridan, who had been staying in Winchester on his way back from a meeting in Washington, heard the fighting and rode to Middletown to rally his troops. A massive counterattack that afternoon routed the Confederate troops beyond Strasburg by nightfall.
Information taken from http://www.nps.gov/cebe/historyculture/long-meadow.htm