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.


This wasn’t always the case. When I moved to Portland in 1992, I was single and still in my 20s. As such, one of my first orders of business was the establishment of decent pizza-delivery options. [I was, for the record, still operating under the delusion that one could get a decent cheesesteak in Maine; I’ve since disabused myself of that notion.] Supreme was right up the street from me and not bad. Silly’s proved the gold standard. What got my attention? The Jamaican Jerk Chicken Pizza. Disappointed this particular pie hasn’t spread; beats the hell out of any BBQ chicken pizza… What sealed the deal for me, at Silly’s? The sublime Thai Pie, with it hunks of sate chicken, daubs of spicy peanut sauce (atop the cheese, away from the lightly applied tomato sauce) and spring onions.

Stage II of my love affair with Silly’s did not begin until I had moved out of Portland (in 1998) and settled with my young family here in the NG. I realized two things when I first walked into the Washington Street location: 1) I had never actually set foot in the place! My relationship with Silly’s, long and intimate though it had been, was entirely take-out based; and 2) this eatery was ideal for small kids. Indeed, my young children immediately took to its uber-casual, aggressively whimsical surroundings.

[I will say, too, that that when Silas was 2-3, i.e. before we moved out of Portland, we stopped into Boru often enough — on our errands — that he referred to it as “The Beer Store.”]

Nothing matched at Silly’s, not the silverware, not the tables & chairs, not the salt & pepper shakers. The young, friendly staff was always decked out in the latest (never-matching) shades of alt-hipstery. It wasn’t loud but my kids sensed immediately that “here was a place where rules aren’t valued or emphasized”.  They loved it immediately. When we first ventured out back into the garden area — a sort of mismatched, low-budge take on Alice’s Wonderland; or something out of Beatrix Potter on acid — they were doubly sold.

For my part, I appreciated all this, too — but not so much as the menu, which always had something EVERYONE wanted to eat, including myself. I quickly realized that as a bachelor I had been ordering for years from one of Silly’s old, perhaps dumbed-down takeout menus (this was pre-Internet of course). The proper, eat-in menu was way bigger, better, and more over the top. Some highlights:

• Best shakes ever: I wish I had a listing to share here; the website today doesn’t even mention its roster of super inventive, high-quality shakes. My favorites included including Tang Creamsicle, Vanilla Guinness, and the inimitable Key Lime Pie — complete with bit of graham cracker crust. They just whizzed up an entire piece of pie in there. Genius!

• Gravy Danger: I am a big fan of fries and gravy (hat tip to my dad and Barry Levinson’s “Diner”). This concoction (“French fries with house made gravy, lots of bacon, melted cheese & scallions”) took the genre to a new level. Yeah, it’s poutine. But during the 1990s, I didn’t really know from poutine.

•  Silly’s was, at its core, a sandwich, wrap and burrito joint. My faves included The Diesel (“Tangy coleslaw, American cheese, BBQ-sauced smoked pork & pickles in a wrap”) and perhaps the best veggie sandwich I’ve ever encountered, the Hashpipe Burrito, comprising veggie burger chunks, tofu, roasted veggies, potatoes, vegan cheese, jalapenos & spicy sauce wrapped in a flour tortilla.

• The Slop Bucket was another example of Silly’s splendid, messy, out-of-the-box thinking: “BBQ smoked pork, brown rice, herbed beans, cheese & tangy coleslaw layered in a bowl with pickle chips around the rim – It’s hot & cold!!” Indeed it was.

I can sympathize with the soon-to-be-ex proprietor of Silly’s. This is a lot to leave behind.

“Please try and refrain from making this a debate about the state of affairs,” Colleen wisely counseled us via FB. “I am sharing with you my reasons and my opinion, which can be taken with a grain of salt, but after this much time in business and so much loyalty I thought everyone deserves to know what is going on with me and my business. I hope I have made the right decision by explaining myself. I am begging you to please make your comments about saying goodbye to an institution and about sharing some good times you had here — so I can look at them and smile, as this is the hardest decision I have ever had to make. So please be kind and you can trash me after I close.”

Wouldn’t dream of it.