The End of a Very Pleasant Trip Down the Chesapeake

So, it was indeed a “very pleasant trip down the Chesapeake” for Oliver and the other 999 boys from Connecticut for two days during the first full week of November 1861. The Nutmeggers were again of cheerful hearts when their steamer tied up to the pier in Annapolis, Maryland on Tuesday evening, November 5th.  As Private Oliver Case and the 8th Connecticut Volunteer Infantry Regiment disembarked at Annapolis on November 5, 1861, they found a city pulled between southern loyalty and northern military force much like their previous transit point in Perryville. This time, they would be more permanent residents. As Maryland and its governor were struggling with the decision against secession only eight months before, the first Union soldiers, in the form of the 7th New York Infantry, arrived in the capital city.

At 4 o’clock P.M. of Monday, April 22, the Seventh Regiment first landed in a hostile State on a military errand, and was disembarked at the dock of the Naval School at Annapolis. The men marched ashore by companies in good order, and formed in regimental line on the beautiful parade-ground in the rear of the Naval-school buildings.[i]

Now the arrival of Burnside’s expeditionary force in the capital city became a continued guarantee of Maryland’s place in the Union. As they had when Union forces first landed in Annapolis earlier in the year, the citizens of the city watched the soldiers arrive by the thousands as both an occupying force and to train the green regiments for future operations deeper in Confederate territory. The most recent occupation of the city by Union troops under the command of Brigadier General Thomas W. Sherman had been designed to equip and train an expeditionary force comprised of three brigades of 13,000 troops. The objective of this new expeditionary unit was to capture one of the important port cities along the lower South Carolina coast in order to give the Union Navy a base of operations for blockading operations. Only days before the arrival of the first units of Burnside’s expeditionary force, Sherman’s brigades had departed Annapolis with a combined naval force under the command of Flag Officer Samuel F. du Pont. On November 7, 1861 just two days after the 8th Connecticut arrived at Annapolis, the Sherman/du Pont expeditionary force attacked and captured both Fort Walker and Fort Beauregard gaining control of Port Royal Sound, South Carolina.


General Thomas Sherman conference

General Thomas Sherman and Flag Officer Samuel du Pont confer on the Great Naval Expedition, November 1861

The “Great Naval Expedition” as it was often referred to in contemporary accounts provided invaluable lessons for Burnside’s expedition that would follow just two months later.[ii] Thomas Sherman and his staff conducted detailed planning with the naval staff of Samuel du Pont ensuring a well-coordinated joint operation between the two services. Logistical challenges associated with moving 13,000 soldiers with their supporting equipment and horses over hundreds of miles of storming seas were addressed and overcome. Most importantly, the tactics and techniques required to successfully employ this joint Army-Navy force against Confederate shore fortifications were developed through a process of trial and error during the Battle of Port Royal. All of these lessons would provide Ambrose Burnside a head start when planning and executing his expeditionary operations against the North Carolina coast in January of 1862.

As General Sherman and his troops were wading ashore in Port Royal, South Carolina, the city of Annapolis was again preparing for occupation by soldiers dressed in Union blue. In April of 1861, Governor Hicks had expressed concerns that the southern sympathies of eastern Maryland combined with the displeasure of the citizens at the military occupation of the city would have a detrimental effect of his efforts to have the state remain in the Union. Hicks’ leadership in keeping Maryland in the Union had not found approval by most of the residents on the east side of the state. By November, Hicks’ concerns remained regard the disposition of the citizens of Annapolis, but the earlier occupation by Sherman’s regiments had gone without major incident. Now, Burnside’s crop of fresh Yankees including Oliver Case would find themselves on the front line of the efforts to improve relations between the citizens of Annapolis and their Union occupiers.

During their first two nights in Annapolis, Oliver and the other soldiers of the 8th Connecticut were billeted on the campus of St. John’s College. The college was originally founded in 1696 as King William’s School only two years after Annapolis was designated as the capital city for the colony of Maryland. The institute was established as a preparatory school, but when it received its charter in 1784 it included a name change to St. John’s College. The college was notable and unique for its time because it espoused a policy of religious tolerance where “youth of all religious denominations shall be freely and liberally admitted” with a focus on rigorous academic pursuits. With the onset of the Civil War, many students departed the school prior to their maturation in order to join either the Union and Confederate armies reflecting the divided loyalties of the host city and state. With most of students gone, the Union army, which had begun to arrive to secure the strategically important city, soon occupied the grounds. College officials watched helplessly as the army established a firm presence in many of the building on campus. By November 1861, the great number of troops landing in Annapolis requiring housing arrangements forced the establishment of large tent cities on the grounds of St. John’s.

When the troops of the 8th Connecticut arrived on the night of November 5, 1861, they were given quarter in the buildings across the St. John’s campus as a temporary housing arrangement until the tent city was operational. Oliver wrote to his sister that “we were quartered in a college where we stayed two nights and one day.”[iii] The campus was comprised of several building that would have been available to house the soldiers of the regiment. McDowell Hall, opened in 1742, was originally built by the Maryland Governor Thomas Bladen to be used as a residence for the state’s executive. However, after the Revolutionary War in 1784, the state gave the yet unfinished building to the newly chartered St. John’s College. The school completed the building including the addition of a bell tower, still in use today, along with a third floor. Although the building was significantly damaged by fire in 1909, it was reconstructed to its original specifications. It was named for the first principal of King William’s School, John McDowell.

[i] (Our War Pictures, 1861)

[ii] (The Great Naval Expedition, 1861)

[iii] (Case)


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