Silly’s main “dining room”, home of the Key Lime Pie Shake and the Slop Bucket

Two pillars of Portland’s bar & restaurant vanguard exited the city’s vibrant but transitional culinary scene last week. First came the announcement that Silly’s, long a boho totem on Washington Street, would close its doors on Sept. 1. Two days later, Brian Boru — the peninsula’s “It” bar for much of the 1990s — announced its doors would close.

In a Facebook post equal parts trenchant and heartfelt, Silly’s owner Colleen Kelley explained that the city, in general, and the Washington Street corridor, in particular, were rapidly becoming too chic for her tastes. She also has an aging father who requires her 24/7 attention, something the restaurant had commanded for the past 31 years.

“My sister Shelley and I have sold the buildings — not Silly’s, just the buildings,” Kelley wrote on the restaurant’s Facebook page. “As much as Erin and Will, the managers, and the rest of the staff are taking care of me and the business, it is constantly challenging to do business with the city of Portland, which also wears me out. Another huge factor in my decision: I am smart enough to know my business model won’t work in a city destined to be Seattle, which isn’t meant to be a slam; it is just my opinion of where Portland is going. I don’t want anything but wonderful things for Portland, Maine. I have enjoyed many years here. However, I am a fat woman who serves fat, over-portioned food and I won’t charge 24 dollars for 4 oz. of dip and some pita bread.”

Not 24 hours before this news broke, a Portland friend had raved to me about a new southwestern restaurant that had just opened on Washington Street, long a gritty thoroughfare that, of late, has gentrified — commercially — thanks to a raft of restaurants, breweries and distilleries. To call these “upscale” is to ignore the inherent casual vibe that pervades all things Portland (I can’t think of a single restaurant in the city where jackets are required or shorts frowned upon). But this much is beyond dispute: Portlandia in 2019 is increasingly posh; the owner of Silly’s has recognized this and wants no part of it.

One key to understanding both closings has nothing to do with Portland’s national rep as a city for haute bourgeois foodies. Note the first sentence Kelley wrote: She mentioned buildings twice. The real estate market in Portland is blowing up; the opportunity for businesses of all kinds to cash out is only a phone call away.

This dynamic was even more evident with the Boru closing. It was announced Thursday, August 22 that its last day would be Monday Aug. 26. This bar sits more or less all by itself in the middle of an open, undeveloped lot — half the size of a full city block. It’s adjacent to the Old Port, walkable from Congress Street and the tony West End; it’s right across the street from the civic center.

Someone clearly made the owner an offer (based on potential/developed real estate value) he couldn’t refuse… Decision-making is rarely so simple as that, of course. See a sensible rundown of the factors contributing to the phenomenon here… It’s not capitalism run amok — just more evidence (as if we needed any) that its churn never rests.

Still, I’m conflicted by all this because while I’ve always loved Silly’s, one of Portland’s great draws — to me, as a 50something residing half an hour north, in New Gloucester — is the fact that when Sharon and I want to dine out, there is ALWAYS some hot new Portland restaurant we’ve been meaning to try. Folks tend to blame hipsters for the Seattlezation of Portland, but we and our middle-aged comrades are part of the problem.

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