On September 12, DeCourcey's tired brigade rested at their hillside camp north of Manchester, Kentucky. The troops resumed some semblance of typical camp life. They would remain here for nine more days.

Meanwhile, the situation back at Cumberland Gap grew ever more serious. General Morgan assessed his situation and, on September 14, held a council of war with his staff. Their options were:
1) choose a route to Ohio that was viable for a large troop movement with heavy weapons and many wagons, knowing a much larger Confederate force was waiting to engage them,
2) to simply surrender the entire division of 12,000 men and all their supplies and equipment, or
3) attempt a daring escape over an impossible wilderness route and at a speed fast enough to elude the enemy who would surely discover and pursue them.
Option 3 was agreed upon and the decision was made to attempt an escape over a route so improbable the Rebels would not discover them in time to stop them. Preparations to evacuate Cumberland Gap were immediately begun.

DAY 1 - On September 17, Morgan sent a dispatch, lead by Lt. Col. George W. Gallup, 14th Kentucky, to the Rebel lines, with the stated purpose of negotiating a prisoner exchange. The real purpose of the contact was to distract the Rebels while the garrison prepared to leave the Gap. The ruse was effective. About 200 soldiers, also lead by Lt. Col. Gallup, posted themselves in the strategic ravines just south of the Gap while the regular pickets returned to the main force now evacuating northward. Eventually the Rebels realized what was happening and sent pickets toward the Gap. Gallup's men fired upon them causing them to fall back, not knowing how many troops they actually faced. Gallup kept the Rebels at bay while Morgan and his huge column moved northward in another extraordinary feat of military ability, leaving the Gap and escaping the encirclement and siege of Confederate General Kirby Smith's troops. When morning arrived (September 18 - Day 2) Gallup's small but brave little force quietly withdrew from their strongholds, burned the remaining buildings at the summit of the Gap and, with his own hand, torched the remaining train of ammunition, left by Morgan, causing a huge explosion as it ignited the principal magazine. The Rebels, knowing the Gap was now evacuated, did not approach for several hours, as they believed further explosions could occur. Morgan's division had made its escape, achieving a distance of 20 miles by daylight, passing by their old Camp Patten at Cumberland Ford (now Pineville) and reaching Flat Lick. Now, a perilous journey of nearly 200 miles lay between them and the safety of the Ohio River.

Pvt. Newt Gorsuch of Company B describes September 18 from his perspective:
Long roll beat at 8 o'clock last night. All the Regts. called out and form line of battle. Sleep with our guns in our hands...

* Information and quotations from Civil War Diaries and Selected Letters of Robert Newton Gorsuch, recently published in book form by Newt Gorsuch's great grandson, Everett Gorsuch Smith, Jr. The book is available for purchase from various Internet sources.