Dennis R. Bailey

Dennis R. Bailey obituary, Windham, CT

Dennis R. Bailey

Upcoming Events

Apr

23

Service

11:00 a.m. - 11:30 a.m.

St. Joseph Cemetery

61 Club Rd, Windham, CT 06280

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Services provided by

Bacon Funeral Home

Dennis Bailey Obituary

Obituary published on Legacy.com by Bacon Funeral Home on Jan. 30, 2026.
It is with great sadness that we announce the passing of our beloved husband, father, and grandfather, Dennis Bailey on Friday January 30, 2026. Dennis was the son of Raymond and Ruth Bailey born on January 29, 1949 in Bluefield, WV. He moved to Connecticut in 1961 and became a long time resident of Mansfield.

After graduating from E. O. Smith high school, Dennis served 4 yrs in the US Air Force with a stint in Pakistan. Upon returning home he resumed a position at UConn in the IT Dept where he had worked part time as a student. He retired from the university in '03 with over 38 years of service as a supervisor on third shift. He made long time friends, especially Ann. He had a life long passion for fishing especially in the Mansfield and Quaddick state parks. He was a member of the Windham Fish and Game club. He also enjoyed many summers camping and fishing in Rhode Island with his family as well a traveling throughout the United States with his wife. He was an avid UConn Women's Basketball fan never missing a game and he especially enjoyed the precious time spent with his family.

Dennis leaves behind his beloved wife of 55 years, Sandy Trudeau Bailey; daughter Karen Bailey and granddaughter, Elyse Macha and members of the Bailey, Lawless and Warinsky families. He was predeceased by his brothers, Raymond, Robert and Carson Bailey.

A graveside service in St. Joseph Cemetery, Windham will be held in the Spring. In lieu of flowers, donations may be made to the Willimantic VFW 630 Valley St, Willimantic, CT 06226. To send an online expression of sympathy, please visit www.baconfh.com

To plant trees in memory, please visit the Sympathy Store.

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January 31, 2026

carole Larned posted to the memorial.

January 30, 2026

Bacon Funeral Home announced events.

January 30, 2026

Bacon Funeral Home posted an obituary.

1 Entry

carole Larned

January 31, 2026

So sorry for your loss of Dennis he will be missed Prayers for you Sandy and your daughter

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Bacon Funeral Home

71 Prospect Street, Willimantic, CT 06226

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Upcoming Events

Apr

23

Service

11:00 a.m. - 11:30 a.m.

St. Joseph Cemetery

61 Club Rd, Windham, CT 06280

Send FlowersBook nearby hotels

Services provided by

Bacon Funeral Home