Roland D. Sherman

Roland D. Sherman, 76, of Southport and Augusta passed away September 6, 2025 at Maine Medical Center in Portland. Roland was born April 2, 1949 in Boothbay Harbor to Sidney Sherman and Dorothy Blake Sherman. He grew up on Southport, attended the Southport Central School and graduated from Boothbay Region High School in the class of 1967. After high school, Roland enlisted in the Coast Guard and served proudly for four years. He served on the Coast Guard Cutter Sherman (WHEC-720) and was then stationed at the Moose Peak Lighthouse in Jonesport.

Roland worked at the Maine Trading Post during his high school years. He also worked for McFarland Masonry before beginning a long career at Blake's Boatyard where he worked for over thirty years. They considered Roland to be part of the "Blake family". He retired in 2022.

He was a member of the Downeast Yacht Club since 1989, and "The Providers Sportsman Club" since its inception. He always looked forward to the annual "birdie" hunting trip with The Providers over the years, and shared many great memories and stories from those trips. Roland enjoyed boating, golfing, watching the Celtics, Patriots, and NASCAR. One of his greatest passions was his love of cars, and he collected many over the years. He spent many snowy afternoons watching the Mecum Auto Auctions from his lazy boy in Augusta. Oh, how Roland loved to drive….anywhere at any time. During the summer, it was not unusual to find him on the road to Machias to visit Helen's Restaurant for a piece of homemade mile-high raspberry pie, of course with whipped cream. By his family, he was known as "Father Christmas" and enjoyed the annual trip upcountry with Stephanie and Finnegan to cut down the family Christmas tree and tip fresh boughs for wreathes, but only after a hearty breakfast at Griswolds in Solon. He loved decorating for Christmas, and truly looked forward to holiday shopping, always making a point to find just the right gift for just the right person.

You just couldn't keep Roland off the dance floor. It was always a special treat to watch how graceful he was while twirling Stephanie to the 60's tunes. Roland was a very kind and gentle soul who will be greatly missed by all who were fortunate enough to know him, especially his grandchildren.

Roland was predeceased by his parents; brother, Timmy Sherman, and sister, Kathy Blagdon.

Roland is survived by his loving wife, Stephanie Sherman of Southport and August; Step-daughter, Emily Jo Bilodeau of Augusta and loving grandchildren, Finnegan and Olivia of Augusta.

Sisters, Vickie Carver of Boothbay Harbor, Paula Sherman of Boothbay Harbor, and Brother, David Sherman and Margaret Hoffman of Southport

Brother and Sister In-Laws, Celeste & Jeff Brown of Southport and Sylvia and Jon Dyer of Augusta.

Special friends Billy, Gary, Joe, Neil, Jeff, Jay, Tim, Jim, Bill and Al, along with his "Thirsty Thursday" buddies at Robinson's, and many, many more.

A memorial service to celebrate Roland's life will be held at 1 p.m. on October 4th at Hall Funeral Home, 975 Wiscasset Road, Boothbay.

Please join Stephanie, family and friends, upstairs at Robinson's Wharf from 2-4pm to share more stories and celebrate Roland and his life well lived.

Arrangements are entrusted to Hall Funeral Home and Crematory, Boothbay. Condolences may be shared with the family at www.hallfuneralhomes.com