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    Three Dollar Deweys

    3.4 (354 reviews)
    Open 11:30 am - 1:00 AM (Next day)
    Updated 3 months ago

    Three Dollar Deweys Photos

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    THREE DOLLAR DEWEYS ATMOSPHERE

    What's the vibe?
    Loud
    Casual
    Good for kids
    Good for groups

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    Recommended Reviews - Three Dollar Deweys

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    Deweys
    Suzy S.

    I live in Denver so this entire meal was an unusual treat. Maybe I am not the best judge for this type of fare, but I do know when something tastes amazing. The bun was toasted to perfection and the lobster was fresh. I absolutely love beer cheese and pretzels and - again - have a hard time finding them in Denver. These were PERFECT. Service was great, too!

    Irish Breakfast Sandwich (St. Patty's Day Special)
    James H.

    3 Dollar Deweys is a Portland staple. You have to understand what the establishment stands for in order to truly appreciate its beauty. Go in, leave your attitude at the door, and have a great time - whether you're there to meet friends, watch a game, or trying to get drinks/food before heading somewhere else in Portland!

    Matt gives his sign of approval with his ketchup salute.

    We started at CHEESE LOUISE!!!!! We wanted to continue the night unsure where to go. We plundered the seas high and low and came to find Three Dollar Deweys. Security was a G and guided us to a bar to rest our weary arms on. Libations were served with haste and the ambiance was electric!

    Vegan meatball sub, add jalapeños
    El H.

    I got the vegan meatball sub, add jalapeños, and it was good. I'm not a huge fan of the brand they use for the meatballs, the sub was a little thinner than I expected, and the host was fairly rude, but it was good.

    Lou C.

    Really nice option for a drink and some food in Old Port. And a really nice vegetarian/vegan menu, which is rare for a pub. Smallish bar, but ample seating all around. The seafood chowder was great, and did not have bacon, so the pescatarian of the group was able to get it. The clam chowder is made with bacon, and the carnivores enjoyed it! Fun story, this place when it first opened was the only place in Maine to have Guinness on tap, and people would come from as far as Bangor to take advantage of it! Service was really good, super friendly, and prices were average. Street parking only, as with most places down in the Old Port.

    12-piece wings
    Peggy X.

    Came here for the first time for a pint with some colleagues, and overall had an enjoyable experience. The pros: - $3 pint of Shipyard Brewing Discovery IPA at all hours - Free popcorn with your purchase (though we did have to ask for it) - A dedicated vegan menu, which is awesome, given how rare it is to find vegan options at a pub - Lots of seating inside The cons: - Though the ambiance is quite divey, the food prices are not - Our server checked in on us often, but in a way that consistently made us feel like we weren't ordering enough food or drink, which injected some unnecessary stress to the whole experience We ordered several beers, the fries, and the 12-piece wings. The food was decent and the beers were a steal. Note that the honey garlic habañero sauce is really, really spicy (and I can handle my spice!). I'm hoping to come back, but only during happy hour to avoid the dinner rush / ordering pressure!

    vegan nachos
    Linsey H.

    Several great vegan options! Labeled well on the menu and actual additions like vegan mayo. I got the new buffalo tofu sandwich and it was delicious. I loved their buffalo sauce. Our server was lovely and checked in on us a lot. Paid parking right in front. The set up of the restaurant is great and comfortable. I would recommend.

    Vegan nachos with vegan chili and guacamole; french fries too.
    Steff D.

    I think it had been 15+ years since I had stepped inside Three Dollar Deweys, but I had heard they now had an intentionally designated vegan menu and I was curious! So my partner and I stopped in early on a weekend day (there was already a queue forming before their 11:30am opening!). Visiting was like a blast from the past. It felt like "old Portland" (IYKYK), completely frozen in time with vintage beer signs and sports posters. Did you know this was the first-ever Portland Ale House? If you haven't been in a while, know that not much has changed atmospherically. Also, there's still all you can eat free popcorn. I will say this: you are NOT COMING to Three Dollar Deweys for a cocktail or a mixed drink. Sorry, but they're bad (both in taste and in creation - my last cocktail here was like drinking vinegar, it also separated in the glass). Stick to a pint or something canned - they're half the price of a cocktail or mixed drink, anyway. Even a glass of wine is a better option. So, why the generous review rating? Because those vegan nachos are INCREDIBLE and might just be the best in the city (... possibly the only in the city?). Rewind a bit: "Why dedicate such a large amount of our menu to vegan, vegetarian, and gluten-free items? Because we believe good food should be enjoyed by everyone, regardless of dietary restrictions or preferences - even in pubs. Grab your folks (or hands) dive right in and indulge knowing we take great care in our food preparation practices, such as regular employee training and dedicated safe spaces." That's super comforting to read, so THANKS Dewey's for this little (love) note on your website. For excellent, filling, satisfying nachos.... the price adds up: it's currently $16 and is a plate of thick, tri-colored, crunchy, salty tortillas with a gooey layer of vegan cheese, very wet pico (comes on the side), and jalapenos. Adding guacamole (an ample 1/2 cup of it, maybe?) costs an additional $4. Adding Veggie Life Jackfruit Chili (which they absolutely smother the nachos with!) costs an additional $6. So, realistically - because the nachos wouldn't be nearly as good without both of those things - it's $26 for nachos. Split between two people with a pint a piece, you're looking at $50ish. Which seems like a lot, but for dramatically less food and smaller drinks you're going to spend the same on, say, french fries and cocktails elsewhere. I've already been back a few times now for this gratifying mound of comfort food! Perfect lunch or mid-day snack!

    Live music on a Monday
    Cindy Y.

    Been going to Dewey's since the late 80's, but rarely go now that I'm older and live out on the boonies. Two things from my recent visit have me regretting that - live music and happy hour. Came here with a friend looking for an affordable place to have a drink after having an expensive fancy cocktail elsewhere. We got there just as happy hour was winding down, but I was able to get a G&T in a pint glass for $5. That's a third of what you would pay at most other restaurants in downtown Portland. Was chatting with a lovely couple "from away" who had just moved here, when live music grabbed our attention. The classic Don Campbell and a young rock and country singer/ guitarist Henry Lowery. Great duo playing an excellent assortment of songs made the time fly by. Looking at Dewey's website, they have live music Sundays from 11-2, and M, W, TH 6-9PM. Tuesday nights are trivia. Nothing going on Friday and Saturday nights because why compete with the rest of the Old Port. Next time I will go back and enjoy the full show, happy hour drinks, and friendly service. What's not to love?

    Pulled port mac and cheese
    Jess B.

    Three Dollar Deweys is always a fun local spot to go to! They have no parking lot but are situated on Commercial Street parking with tons of spots, as well as many side streets and parking garages close by. Parking is usually hectic as downtown Portland is immensely popular. Dewey's has tons of seating inside - two bars to sit at, high tops, booths, and tables. They sometimes have live music, which I lucked out and got to experience when I went. The pricing is decent and slightly lower than average for the area. They have tons of food and drink options. Food is mostly pub food but a great assortment of options from burgers to salads to mac n cheese to sandwiches. They have a rotating cocktail menu plus full bars so basically most drinks you could think of. We just got a beer and vodka with pineapple juice. Both were very good. We got the fried chicken sandwich and pulled port mac n cheese. The sandwich was delicious - chicken spiced and cooked perfectly. So juicy and delicious. The mac n cheese was a great portion, cheesy, tasty, and makes you want to go in for another bite. Our service was pretty good. Great to start off and then not so great as it got very busy very quickly. We ended up waiting 25 minutes for our check which is why I removed a star. The live music really made the atmosphere fun and care free. The building and bathrooms are handicap accessible. This is a wonderful place for a first date, getting together with friends, or just a cool spot to grab a drink. I will continue to keep coming back!

    Jessie H.

    We stopped in to watch a football game and service was ok. They had a free popcorn machine so that was awesome but did find friendlier service elsewhere.

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    2 years ago

    Bacon wrapped scallops were great and the Reuben with fries was phenomenal! Waitress was not the best but the food made up for it!

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    Page 2 of 9

    Ask the Community - Three Dollar Deweys

    Are kids allowed during lunchtime?

    Yes

    Are dogs allowed?

    It is a bar/restaurant. Why would they allow dogs? We have health ordinances.. I love dogs. But not in restaurants

    View All 3 Questions

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    Three Dollar Deweys - tradamerican - Updated June 2026

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