At the age of 20, Reginard was enslaved by the Ruffians until he was freed and fought in the Battle of Bywater and protected his brother during the fight. Later on September 12, 3001 3A, Reginard Took went to Bilbo's Farewell Birthday Party held in with his family.
During the War of the Ring, Reginard and his brother joined the Shire Company under the leadership of Will Whitfoot. Together, they travelled south to Gondor where they would prepare for war. After the Battle of Pelennor Fields ended, Reginard and his brother volunteered in gathering the wounded and sending them to Minas Tirith. He later participated in the Battle of Morannon and was among those killed.