OWLS HEAD — Robert Lee Liberty, 90, died peacefully due to complications from COVID-19 on Thursday, October 14, 2021, surrounded by his wife and children at Pen Bay Medical Center in Rockport.

Bob was born in New Richmond, Wisconsin on September 20, 1931. He was the eldest of five children born to Lyle and Elsie Liberty. Following graduation from Somerset High School in 1949, where he captained the football team as its quarterback, Bob then served his country in the Air Force until 1951.

Returning to his home state, Bob graduated from the University of Wisconsin at River Falls in 1957 while traveling the country full time for Andersen Window Corporation as a salesman. On one of his trips, he met his wife, Dottie, who was working as a stewardess. They were flying on a DC-6 from Chicago returning to Boston where they both lived. Bob and Dottie were married in 1965. During another one of his trips while still based in Boston, he discovered his next big opportunity to be launched in Rockland, Maine.

It all began in 1964 when Bob and his then partner, Ike Bemis, developed and constructed the first 32 rooms that became the Trade Winds Motor Inn overlooking beautiful Penobscot Bay. Relying on his extraordinary work-ethic and love of construction projects, he never looked back buying or developing a total of seven Midcoast Maine hotels under the umbrella known as Liberty Hospitality of Maine over the next 57 years which included the Deep Harbor Motel, the Camden Rockport Motor Inn, the Country Inn at Camden Rockport, the Cedar Crest Motel, the Navigator, the Glen Cove Inn and Trade Winds on The Bay timeshares.

These hotels would also house numerous restaurants, bars, health clubs, physical therapy offices and a travel agency. When the gas shortage hit in the 1970s he installed a gas pump to make sure his guests had access to gas. When he wanted to offer his guests a fresh supply of lobster and seafood, he bought a lobster pound and a salmon farm both on Beals Island, Maine. He had a solution for everything. He was the Tom Brady of entrepreneurs, still working every day even as he was recently celebrating his 90th birthday. His statistics are astounding over his 57 years in the hospitality business; Bob welcomed over 1.5 million guests to Midcoast Maine, he’s spent $150 million in the local economy, and he’s met over 2,000 payrolls. This was all accomplished without ever having an email account nor a smartphone.

Bob was generous with his time and resources to dozens of local and state organizations. He was a tireless promoter of Rockland’s and the State of Maine’s tourism industry providing his service to the Rockland Chamber of Commerce, the Maine Innkeepers, the Maine Publicity Bureau, the Big E in Springfield, Massachusetts, the Maine Lighthouse Museum, Maine Film Commission and the Rockland Lobster Festival. Bob was instrumental in bringing the Maine Lobster Boat Race series to Rockland Harbor. Over his career he has been named Rockland’s Chamber of Commerce Person of the Year and the Maine Innkeepers Association’s Innkeeper of the year. He supported his parish, St. Bernard’s Catholic Church, in countless ways including donating a TV every year for their annual Christmas Bazaar Raffle.

His generosity extended to many individuals. He was always willing to give a hand-up. If you needed a roof over your head or a hot meal in the cold of winter, and you were willing to work a couple of hours, he would make sure you did not go without. He, along with his wife of 57 years Dottie, provided an immense sense of security to his children and grandchildren as well as his large extended family of brothers, sisters, nieces and nephews. They knew they would always have a safe place to lay their heads, put in a day’s work, or enjoy a vacation day at the beach. Bob was a trailblazer for his children. He was a mentor, leader and coworker. He provided them with the best education, opportunities to travel and strong family values. He was Laurie’s guiding light supporting any path she chose. Aimee and Stephen inherited his passion for hospitality largely due to the fact that Bob made his ventures family oriented. Bob showed his kids the ropes, and his entrepreneurial spirit will live on through their careers. Bob’s daughter Vicki was grateful for the love they shared and for the time they had together.

Bob’s grandchildren, who knew him as Pepére, were his pride and joy. Pepére was their number one fan never missing an opportunity to attend dance recitals, ball games, cheer competitions, graduations and countless other events whether in Maine, Massachusetts, New Jersey or Florida. He ensured his grandchildren had the resources to attend the colleges and universities of their choice. His practical nature prevailed when encouraging career paths that didn’t require a secondary degree. Pepére instilled a sense of independence in his grandchildren, and they knew they were always supported in following their dreams.

Bob loved his old cars in spite of having virtually no mechanical inclinations. His favorites included the 6-door Chrysler Brougham Limousine, the1980 Cadillac Funeral Flower car, a pair of 1972 Cadillac Eldorado convertibles (one red and one white) and most recently his 1993 Cadillac Alante.

Bob was an avid skier well into his 80s. December, February and March you could find him at the Camden Snow Bowl (where he earned his 80+ Ski Club patch) or on Sugarloaf Mountain. In January you could find Bob and Dottie in sunny Cancun or Aruba, riding camels in Morocco, jumping off moving trains in Barcelona, or catching sailfish in Acapulco. They especially enjoyed a recent Viking cruise down the Danube River. October brought annual trips north to Quebec to see the fall foliage. And for 57 years his heaven on earth was his home on Lucia Beach. Always possessing a love for sports, Bob became an avid Boston teams enthusiast while remaining loyal to the Green Bay Packers. He particularly enjoyed countless Red Sox games through the years first with his children and then his grandchildren.

To quote Bob from the Trade Winds 50th Anniversary publication, “I wouldn’t change anything. I’m an optimist. I’ve never been unhappy a day in my life.”

They do not make them like Bob Liberty anymore.

Bob is survived by his wife, Dottie Liberty; their daughters Aimee Liberty of Owls Head, Maine, and Laurie Liberty McKenna along with her husband Michael of Danvers, Massachusetts; son Stephen Liberty and his wife Lisa of Orlando, Florida; and by their grandchildren, Liberty, Duncan and Harrison McKnight, Daniel, Christian and Isabel McKenna, and Brindsi, Brielle and Delaney Liberty.

Bob is also survived by his daughter Vicki Ciernia and her husband Mike of Round Rock, Texas; and by five grandchildren Joey, Matthew, Charlie, Jenna, and Tori, and six great-grandchildren.

He is also survived by his sister, Peggy Koehler, and her husband, Darrel, of Somerset, Wisconsin; and brother, Jim Liberty, of New Richmond, Wisconsin; as well as many cherished nieces, nephews and a large extended family.

He was predeceased by his parents; sister Patty Higgins Foster, and her husband, Bill Foster, and Patty’s son, Michael Higgins; and Bob’s brother, Michael Liberty.

A funeral mass will be held Friday, October 22, 2021, at 11 a.m., at St. Bernard’s Catholic Church, Saint Brendan the Navigator, 150 Broadway, Rockland, Maine. For those unable to attend in person, a live-stream of the service will be available on Bob’s book of memories at www.bchfh.com. Please follow the link under Photos & Videos Tab then Watch Webcast.  

A reception will follow the service at the Top of the Rock, 5th floor of the Trade Winds Inn, 2 Park Drive, Rockland.

In lieu of flowers, the family requests donations be made to The Kitchen Fund, Sussman House, C/O PenBay-Waldo Healthcare Foundation, 22 White Street, Rockland, ME 04841.

To share a memory or condolence with the Liberty family, please visit their Book of Memories at www.bchfh.com.

Arrangements are in the care of Burpee, Carpenter & Hutchins Funeral Home, 110 Limerock Street, Rockland.