Sidney P. Tripp

PORTLAND – Sidney P. Tripp, 60, of Neal Street, died unexpectedly at his home on Sunday, Dec. 20, 2020.

Sid was born in Portland, Maine, on Sept. 7, 1960, the son of Sidney P. Sr. and Mary A. (McGuire) Tripp. He graduated from Maranacook High School in the class of 1979 and then earned his bachelor’s degree from the University of Maine at Orono in 1983.

Sid spent his entire career working in advertising and marketing and in 1993 founded Proactive Resources. With his creative mind, strong work ethic and charismatic personality, he quickly established a very reputable and successful company which led to him becoming a driving force in the Portland business community.

Sid will always be remembered for hosting 20 years of Portland’s biggest Halloween bash. He was instrumental in the lineup of entertainment for Portland Pride for many years and in 2010 founded Downeast Pride Alliance, DEPA, a business networking group which met monthly on a social platform. Affectionally referred to as “The Mayor of Portland,” Sid made friends everywhere he went. Portland will miss his larger than life personality and his wicked sense of humor.

A lifelong lover of antiques, Sid loved scouring flea markets for his next great find. He enjoyed nothing more than opening his home to his family and friends, welcoming everyone with a big hug, cocktails at the ready, ’80s music in the background and a fabulous meal at a perfectly-set table. Sid was truly the ultimate host. He took much pride in his beautiful home and lovely garden, the envy of the West End. He enjoyed travel, especially summer trips to Nantucket and his many visits to Greece including one with Freddie and Paige to celebrate his 50th birthday. One of his last great adventures was taking his beloved niece, Rachael Mary-Grace, to Paris for her 30th birthday.

Sid is survived by three sisters, Terry and her husband Stephen Comeau of New Jersey, Sandi and her husband, Dale Flagg of Augusta, and Rose Weymouth and her partner Lee Godin of Belgrade; his best friend of 32 years, Frederica “Freds” Jackson of Portland; nieces and nephew, Rachael Tripp and her fiancé, Tyler Daigle of Scarborough, Sgt. 1st Class, Aaron Flagg of Germany, Hannah and her husband Ian Doe of Biddeford, Sydney Comeau of New Jersey, and Eva Flagg of Augusta.

Sid’s family would like to extend a special thank you to all of the amazing doctors, nurses and friends who cared for and supported him.

Visiting hours celebrating Sid’s life will be held on Saturday, Jan. 2, 2021, from 2-5 p.m. at the Conroy-Tully Walker South Portland Chapel, 1024 Broadway, South Portland. Following state mandates, and for the safety of all in attendance, face masks are required. A celebration of Sid’s life will be held at a later date. To view Sid’s memorial page, or to share an online condolence, please visit

Those who wish may make contributions in Sid’s memory to: American Heart Association, 51 US-1 # M,

Scarborough, ME 04074

or to the Animal Refuge League

217 Landing Road

Westbrook, ME 04092

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