Freeport – Thirty years ago, teetering toward bankruptcy, Freeport was facing the threat of a state-ordered shutdown of its government.

Enter the newly hired, 32-year-old town manager, Dale Olmstead Jr.

“On my first day at work, I learned that Freeport hadn’t had a required audit in three years,” said Olmstead. “It was on the verge of bankruptcy. Past councils had spent all of its reserves and fund balance. Moody’s and Standard & Poor’s had taken away our bond rating. We couldn’t borrow money and because we couldn’t track receipts, the state auditors were threatening to close our doors.”

Thanks to some hard work by Olmstead and others, the town pulled itself out of the morass of the early 1980s – something that he now says is one of his proudest achievements during his tenure as town manager. As Olmstead, 62, prepares to retire and hand the reins over to new Town Manager Peter Joseph, Freeport finds itself on strong financial footing and looking forward to a healthy future.

Olmstead and his wife Barbara, who recently retired as the English department coordinator at Bowdoin College, are building a lake house in central Maine, and Olmstead said he is looking forward to enjoying his new home, especially after delaying his retirement a short time at the request of the Town Council.

“I was encouraged by several councilors to stay another six months and was finally talked into it,” he said.

Town Council Chairman James Cassida said the town owes a debt of gratitude for all Olmstead has done for Freeport.

The (residents) of Freeport are extremely thankful for Dale’s contributions to our community over the past 30 years,” Cassida said. “Dale has always been a strong advocate for Freeport and has worked tirelessly to position our community to be successful in whatever endeavor town leadership or the citizens have directed. Thirty years ago, Dale inherited a community in financial disarray and through his strong leadership has transformed our community into a model for fiscal structure and health. Because of his strong fiscal management we have been able to weather the difficult economic times over the past several years without the huge fluctuations in the tax rate experience by many other communities. Dale’s contributions to Freeport will leave a lasting legacy and he will be missed by all who have worked closely with him.”

Olmstead’s last day on the job is Oct. 18, and he has been working with Joseph to help ease the transition.

Olmstead came to Freeport on July 26, 1982, after serving as assistant town manager in his hometown of Caribou. He said he sees some similarities between himself and the 30-year-old Joseph, who came to Freeport after serving as the town manager in Lincoln, N.H.

“The Town Council in 1982 took a chance on a 32-year-old assistant manager from northern Maine, with the hope that that manager would have a long tenure,” he said. “I think that this council had the same goal in mind. They took a chance on a 30-year-old manager from a small town in New Hampshire. I know in talking to my councilors, they hope he has a long tenure here.”

Joseph said having Olmstead around to help through the transition has been invaluable.

“He’s been very helpful,” Joseph said. “It’s not common (to have the old manager around as part of the transition). You don’t often have that opportunity. It becomes more important when you have somebody with the level of information (that he has). He’s got the 30-year background. He’s really got information that goes back further than almost any other employee.”

In fact, Olmstead can call on experience that goes back to a time before Freeport was known as a tourist destination for shopping. When he first arrived in town, other than L.L. Bean, there was very little retail in Freeport, though it was starting to sprout modestly.

“When I arrived in 1982, Freeport was just beginning to have its retail boom,” Olmstead said. “The only outlet that moved here was Hathaway Shirts. Other than that, Main Street was in a state of renovation. The Dansk building (on Main Street), that had just burned and I can remember the demolition trucks sitting along Main Street cleaning the debris out of the burned shell.”

But burned buildings weren’t the biggest problem facing the town. Almost immediately, Olmstead learned that Freeport’s financial picture was in complete disarray.

Olmstead quickly went to work to fix the situation.

“I went to the council on the second day of my tenure and asked for an executive session,” Olmstead said. “(I) told the council that none of this was revealed to me in my interview, and the answer I got was, ‘We couldn’t afford to let this cat out of the bag. If anyone found out we would’ve all been in trouble.’ So I told the council we had to get some professional financial help.”

The council agreed, and Freeport’s finances eventually were put in order.

“Today, we have a fully funded reserve and a fully funded fund balance and we’ve achieved a double A+ bond rating,” he said. “One thing the new manager will not have to worry about is Freeport’s finances as long as councils going forward stick to the financial policies that have been adopted over time.”

But Freeport wouldn’t enjoy its financial situation today without its retail base. And when talking about retail in Freeport, the conversation naturally begins with L.L. Bean. Olmstead said the company has done countless things to benefit the town, from donations to the fire and police departments to big celebrations like July’s commemoration of the company’s 100th anniversary.

“L.L. Bean has been an amazing corporate citizen,” Olmstead said. “They’re incredibly good to work with (and) they go out of their way to stay out of local politics. I spend more time soliciting their input than they spent giving me their input. What they’ve given this town since I’ve been here is just phenomenal.”

Olmstead said that as he began as town manager, investors started looking to piggyback on Bean’s success and bring more shops to town. He cited George Denney, who brought some of the first outlets to town in the early 1980s, as one of those pioneers. Denney, the former chief executive officer of the internationally known Cole Haan shoe company, opened the first Cole Haan retail outlet store in Freeport in 1982, kicking off a retail explosion that remade the town into the major tourist destination that it is today.

“George Denney played a huge role in transforming Main Street,” he said. “George built a series of buildings along Main Street and renovated those buildings and they went from local business to retail.”

For his part, Denney said that Olmstead has been “a very good town manager.”

“He’s meant an awful lot (to Freeport),” Denney said, adding that Olmstead has worked to help businesses grow in town.

“Twelve years ago I started the Freeport Community Improvement Association,” Denney said, adding the association, a volunteer organization of residents, merchants, business and property owners, took on the task of helping clean up downtown, rebuilding local parks and putting in granite benches along Main Street. The association, with Denney as chairman, continues its work to this day. “We did a lot of things, and Dale was behind us all the way,” Denney said.

As he gets ready to leave town, Olmstead said there is much he will miss.

“What I’m going to miss most is interacting daily with the employees that work here. It’s a great group,” he said. “

“This is one of the few jobs I know of where you can actually really positively impact someone’s life. I see people day in, day out with problems that they need help with,” he said, “and it’s a great feeling to be able to help them out.”

But while he will miss the people, Olmstead said he is ready to retire. “This is been a wonderful career,” he said. “But after 35 years (working in Freeport and Caribou), I’m really looking forward to doing something totally different.”

“This is one of the few jobs I know of where you can actually really positively impact someone’s life,” says Freeport Town Manager Dale Olmstead Jr., relaxing in his office. Olmstead retires Oct. 18.