ENGLEWOOD, Fla. – Herbert Freeman Winslow, born in Beverly, Mass., to Edward and Pauline Winslow on July 25, 1949, passed away peacefully at his home in Englewood, Florida, on Feb. 12, 2024, accompanied by his wife, Genevieve, and his feline friends, Bugster and Little D. Herb had battled illness off and on for over 20 years. He would rebound for a long stint, get his mojo back, then become symptomatic again. All things considered, Herb felt that he was very fortunate to have lived as long as he did. Anyone who had the great pleasure of knowing this amazing well-rounded and talented man would have to agree that Herb offered something very unique and warm to just about everyone he encountered. He was endowed with a remarkable quick wit and a great sense of humor, an intelligent man with with a plethora of diverse knowledge. Herb had the gift of getting a crowd of people laughing in stiches from his personal stories and endless jokes. A man of great principle, he was loyal to his good friends and loved them as if they were family. A lifetime Red Sox fan, he loved to tell about his boyhood trips into Boston to watch the Red Sox play at Fenway.

After high school Herb attended Stetson University in Deland, Florida, then trasferred over to Nasson College in Springvale. It was at Nasson that he met his lifelong friends and also found his calling. While there, Herb landed his first night manager/bartender position at a local lounge. It was a perfect fit for him from the very start. Herb was good with people, a natural entertainer and a sports fanatic suitable for the job. He liked engaging with the customers that came in from all walks of life. In the late 1970’s Herb partnered up with his college friend to open up a rock n roll nightclub, the Free Street Pub, located in Portland. After the doors closed to the Free Street Pub, Herb continued working in the restaurant/bar business until his early retirement.

Herb loved surf-fishing for stripers at Higgins and Scarborough beach. His largest striper was measured at 49.5 inches and he very was proud of that one. Interestingly enough, Herb didn’t eat fish so he would catch and release, using saltwater desolving hooks just in case, a real conservationist at heart. His other hobbies were fly-tying, boating and lake fishing, also enjoyed travelling and was an avid reader. Being a nature lover, Herb valued his 43 years spent living on Sebago Lake with all it had to offer. He pretty much on a daily basis would head for the local hangout to meet up with his peeps to talk sports, fishing, music, politics, or just about anything else that popped up in conversation, forever hopeful to round up enough people for a poker game out on the back deck. Last but not least, he always looked forward to the annual trip to Las Vegas with his best friend Jimmy, during March Madness.

Herb is survived by his brother, Samuel Winslow (wife Lisa) Baton Rouge, La., and his sister, Laurie Shamano (husband Gary) Hudson, N.H., and all of his nieces and nephews.

There will be a service for Herb later this year – to be announced.

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