Meet the New Bear… 

Newfound Bears (from left): Mike and Byrd Dickson, Andy Pillsbury. photo/Tom Major

With the tourist season in full bloom, most Maine restaurants are making the money they count on to carry them through the lean winter months. But not the true local places.  

“When it starts to be fall and winter … we start making more money,” said Andy Pillsbury, one of three new owners of the Great Lost Bear, the iconic Forest Ave. bar and restaurant in Portland’s Woodfords neighborhood. “What people don’t realize is that our bread and butter, the heart and soul of this place, is the locals, year-round,” Pillsbury added. “We are first and foremost a local bar.”

Dave and Weslie Evans opened the Bear in 1979 with Dave’s cousin and business partner, Chip MacConnell, who sold his interest and retired a few years ago. Back then, there were fewer brewing companies in the entire U.S.A. than Maine has now. But when local beer arrived, the Bear was there to champion it.  

After 44 years as owners, Dave and Weslie sold the Bear this spring to three of their longtime managers: Pillsbury, and Mike and Byrd Dickson.  

“We’re not really big on titles around here,” Pillsbury told me at the bar last month. “If we had to break it down, Byrd was the general manager, so she did the payroll and all the back-office stuff. Mike was the bar manager. I split that duty with him.”

“But now, we’re all just owners,” Byrd added. 

Seven years before Maine’s first brewery opened, the Bear aspired to be Portland’s best burger joint. And soon after microbreweries arrived, the Bear’s reputation as the spot for local and regional craft beer was secured. 

“It was Chip’s idea,” Dave said of the bar’s embrace of craft beer. Geary’s Pale Ale went on tap as soon as it was available, and Gritty McDuff’s Pub Style followed two years later. Dave recalled a few early breweries that didn’t last, including Casco Bay and Sparhawk. And he remembered driving to Massachusetts for beers that were not yet distributed in Maine, like Sam Adams, Ipswich, Commonwealth and Watch City. 

Byrd Dickson also recalls traveling in the early days to get beers from breweries that weren’t being distributed. “We used to go up to Sea Dog in Camden,” she said. “Kai Adams [co-founder of Sebago Brewing] was the brewer there. He was just a little kid, but he rolled out a barrel of Blueberry Ale for us.” 

Adams remembers that well, but recalled an even earlier Bear sighting. “I first met Dave, Chip and Mike when I was brewing at Oasis [Brewing Company, in Denver]. They had come out for the Great American Beer Festival in 1992, and we won a medal for our stout. They stopped by the brewery and said they were from Maine.” 

Adams, who’s also been a leader of the Maine Brewer’s Guild, credits the Bear with being a positive influence on the development of Sebago Brewing, and on Maine craft beer generally. “I’ve always said that you haven’t really started a brewery in Maine until you put your first keg on tap at the Great Lost Bear,” he said. “From 2012 through 2018, I tried to attend all the Thursday Night Showcases featuring new breweries. I’d meet everybody, and then I’d get up with the bullhorn and introduce the brewers. It was really fun to see their eyes as they realized, after all their planning and preparation, it was finally real.” 

The Bear’s special place in the history of Allagash Brewing is celebrated on a plaque over the bar and with a dedicated row of taps called Allagash Alley. Every July, the folks from Maine’s largest brewery return to the Bear to celebrate the first pint of Allagash White ever sold. Legend has it that Allagash founder Rob Tod would sometimes sit at the bar buying strangers pints so they’d give his beer a try. Most customers weren’t impressed by this hazy wheat beer with its peculiar yeast flavor, but Dave and Mike kept it on tap until it was popular. For years now, it’s been the single best-selling beer at the Bear.  

“I think they’d be fine without us,” Dave said of Allagash, and joked that they had to keep pouring Allagash because “we were desperate for anything to fill the taps.” 

“The folks at the Great Lost Bear were the first to take a chance and put my beer, Allagash White, on tap,” Tod, now the owner of the 20th-largest craft brewing company in the country, wrote via e-mail. “And since then, they’ve been institutional in supporting and expanding the popularity of the beer scene here in Maine.”

Rob England, sales director at Rising Tide Brewing, agrees. “This is one of the original craft beer places in Portland,” he remarked while at the bar with Rising Tide founders Nathan and Heather Sanborn for their brewery’s Thursday Night Showcase. “Besides the fact that it is an institution, Mike and Byrd are cool as shit. We like hanging out here. This isn’t just a place where you come and have a pint. I love the food. I love the ambiance. I love the square bar, because you actually see everyone at the bar, make eye contact, see what’s going on, see what that guy’s eating and drinking. Nathan just housed a plate of wings.” 

Shea Hearsum Cusick, Executive Director of the Maine Brewer’s Guild, recalled an experience at the Bear when she was just starting out as a sales rep for Nonesuch River Brewing, in Scarborough. “When I first started selling beer for Nonesuch, I wasn’t accustomed to all the nuanced ways that buyers at bars could, well, in essence, tell you to shove off,” Cusick said. “I went to the Great Lost Bear to get a beer and regroup one afternoon, and I saw Mike [Dickson] there. I didn’t know him at the time, but I figured he was the buyer because he was in deep conversation with another rep.

“I waited until the other rep left and introduced myself, and asked if he would like to order a Nonesuch Red keg,” Cusick continued. “He was like, ‘Sure! Have one added to my Tuesday delivery.’ It was my first actual yes. I was beside myself. I sat there talking to this really nice bartender lady, Byrd, for a bit. Then I paid my tab and left. As I walked out the door I realized that I had absolutely no idea how to get that keg added to his order. Good thing I figured it out, because Mike and Byrd and Andy have continued to order beer and set up showcase nights for me and Nonesuch since.”   

The Bear’s steadfast support of local beer has been a model for others. The Thirsty Pig, on Exchange Street, has nothing but Maine brews on tap. Several standout Maine beers, including The Substance IPA from Bissell Brothers Brewing, made their debut outside the brewery there. Thirsty Pig co-owner Dave Nowers is still a regular customer at the Bear.  

“I’ve got to get the Dirty Wings every once in a while,” he said. Nowers spoke of the community of Portland restaurants that respect and support one other. A fine example of that spirit is Man Bear Pig, a special brew made by Rising Tide in collaboration with the Bear and the Pig.  

Lily Dickson, daughter of the new owners and a Bear employee for about 15 years, pointed out that their haddock comes from Harbor Fish Market, on Portland’s Custom House Wharf, all the produce comes from Native Maine, and all their bread comes from one of their Woodfords neighbors, Big Sky Bread Company.  

Pillsbury is quick to reassure anyone who asks that nothing is likely to change much under the new ownership. You don’t fix what ain’t broken, and he and the Dicksons have been making most of the operational decisions for the last few years, anyway.  

Dave and Weslie will continue to be part of the bar. Weslie’s wonderful artwork has decorated the Bear’s menus, ads and merch for decades. The new owners hope that’ll continue. 

“I’m consulting with these guys,” Dave said. “That means I still get free beer. But they’re not paying me.”

The Great Lost Bear, 540 Forest Ave., Portland, is open from noon to 10 p.m. daily. More info at

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