Chester R. Flagg Jr., 56, of Gardner, died peacefully Monday, August 31, 2026, in Saint Vincent Hospital in Worcester, after a period of declining health.

Born in Gardner on July 7, 1970, he was the son of the late Chester R. Flagg Sr. and Ethel "Annie" (Beal) Flagg. Chester was an extruder operator employed by Bemis for several years.

Chester loved spending time outdoors, especially fishing and going off-roading in his truck. He enjoyed the freedom of being outside and the simple pleasures that came along with it. Above all, Chester's greatest love was his family. He treasured the time spent together and the many special memories, stories, and laughs they shared throughout the years.

Chester is survived by his two sisters, Debra Singpradith and her significant other, Mike Valadez, of Phoenix, AZ, and Kelley May of Phoenix, AZ; two nieces and two nephews, Nicole Souvandara of Florida, Jennifer May of Baldwinville, Joshua May of Fitchburg, and Nicholas Singpradith of Phoenix, AZ; his aunts and uncles, Ellen Chapman and her husband, Harold, of Baldwinville, and Mary Norbutus of Athol; and several cousins.

A Celebration of Life will be held Saturday, September 5, 2026 from 12:00 p.m. to 4:00 p.m. at The American Legion, Eugene M. Connor Post 193, 295 School Street, Winchendon, MA 01475

In lieu of flowers, memorial contributions may be made to Alyssa's Place, 297 Central Street, Gardner, MA 01440 or on their website at www.alyssasplace.org. Please reference in memory of Chester R. Flagg Jr.