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Angie Bryan

Angie Bryan is a former diplomat who is enjoying getting acquainted with her new home in Portland, one cocktail at a time.

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Posted: May 20, 2019

Three Dollar Deweys keeps the popcorn, adds a cocktail list in new incarnation

Written by: Angie Bryan

Tables at Three Dollar Dewey’s in Portland’s Old Portland. Photos by Angie Bryan

Relax – there’s still free popcorn at Three Dollar Deweys, the Old Port institution that reopened in March under new ownership and management and with a new chef and bar manager.

The new and improved version of Three Dollar Deweys includes some slight layout changes, nicely renovated bathrooms and a menu revamp that I’ll discuss later, but by far the most exciting development, in my opinion, is that there’s now a specialty cocktail menu featuring 10 drinks ranging from $8 to $13. I went with the $11.50 blood orange martini, one of my drinking companions ordered the $13 Commercial Street (tequila, apricot brandy liqueur, cranberry juice and fresh lime juice), and my other friend chose the $12 Paloma (tequila, grapefruit juice, agave nectar and soda water).

Good news: Three Dollar Deweys now has specialty cocktails – and the free popcorn didn’t go anywhere.

We enjoyed all three drinks, but the surprise winner was something we ordered later in our visit – the $9 Dewey’s Mixer, a repulsive-sounding concoction of lemonade, Deep Eddy lemon vodka and – wait for it – Cabernet Sauvignon. I am not making this up. Intrigued, we asked our server (who was phenomenal) about it. When she reframed it in the context of sangria, a drink that successfully melds red wine and citrus, we ordered one with three straws and steeled ourselves for the nightmarish kind of sensation I experienced when I had my first pickleback. To our surprise, the drink was thoroughly enjoyable from beginning to end – I’d actually order it again. (To be clear, that is NOT how I felt after consuming my first – and last – pickleback.)

For those of you who aren’t as focused on cocktails as I am, Three Dollar Deweys also offers two sparkling wines by the glass ($9 to $10, as well as bottles of Veuve if you’re feeling fancy), 10 white wines by the glass ($7 to $11), six red wines by the glass ($8 to $11), more than 30 beers on tap (most around $6), and an equally extensive selection of bottled and canned beer, 11 of which are local (most around $7).

Dewey’s extensive space features two big bars with wooden barstools with backs (and electrical outlets and purse hooks underneath), loads of high-top tables, booths, and a few larger communal tables. There are TVs and some merchandise for sale, and the service is friendly and accommodating. There’s live music on Fridays and Saturdays, as well during the Blues Brunch on Sundays.

Mac and cheese, a lobster grilled cheese sandwich and an avocado salad from Three Dollar Dewey’s

The new chef has significantly revamped the food menu, adding items like $16 macaroni and cheese, $12 poutine and an entire section devoted to sliders. All burgers and sandwiches are available on gluten-free bread, and the menu clearly identifies gluten-free and vegan options. There’s even a $12 vegan grilled “sausage” board featuring Beyond Sausage. Another highlight? A $5 side of sweet potato tots.

The first time I came to Portland as a tourist, before I decided to move here or write about the bar scene, I went on a walking tour of the Old Port. My tour guide told me that the building Three Dollar Deweys is in used to be a brothel, which inspired the name. I don’t know if that’s true or not, but that’s what I plan to tell future guests as I make them order a Dewey’s Mixer.


WHERE: 241 Commercial St., Portland
PHONE: 207-772-3310
HOURS: 10 a.m. to 1 a.m. Monday through Friday; 9 a.m. to 1 a.m. Saturday and Sunday
AMENITIES: TVs. Blues brunch on Sundays. And did I mention the free popcorn?
BOTTOM LINE: Still a great place to go in the Old Port, especially in a group of friends with different tastes.

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