While men from North Stonington joined several Connecticut regiments during the Civil War, the best-known of these was the 21st Regiment of Connecticut Volunteers because its "G" company consisted completely of North Stonington residents. The 21st, arriving in Virginia, saw its first major combat in late 1862 during the Battle of Fredericksburg, endured heavy casualties at Drewry's Bluff in 1863, and participated in Grant's drive on Richmond in mid- to late 1864. Attrition was so high among officers in the regiment that North Stonington resident James F. Brown, who entered the war as commander of "G" company, ended the war as a lieutenant colonel and commander of the regiment. William S. Hubbel, who enlisted in the regiment from North Stonington, earned the Medal of Honor for capturing a large number of Confederate soldiers while leading a small raiding party in 1864.