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Wednesday Night at Costello's, Jamaica Plain and O'Leary's, Brookline

We went over to Costello's Tavern in JP last night for dinner. The place looks like a dive from the outside, but it's not a bad place. The people were friendly and it looked like a mix of older JP locals and a younger, artsy crowd. We tried the Costello burger (blue cheese and bacon) and the steak tips, as well as the chili cheese fries. The fries were out of this world, while the tips had a nice marinade (tasted like a bit of garlic mixed into it). The char-broiled burger was good, but a bit dry. The bar area reminds me so much of the bar at the long gone Nick's Beef and Beer House's bar (in Cambridge). One plus was that the jukebox had Cheap Trick on it, so I give Costello's some bonus points for that. ;-b

We then went up to O'Leary's in Brookline for a nightcap. Maybe I'm getting old, but I really, really liked the mellow vibe of the place. Quiet Irish music was piping through the speakers, while mostly older folks were sitting at the bar, reading books and chatting with the bartender and waitress. Maybe I liked the place because it felt so much like the quiet hotel bars I like to go to when I'm in Ireland (it looked and felt very much like the old Metropolitan Hotel bar in Kilkenny). I don't know how the food is, since we just went for pints, but the older gentleman next to me (who was cracking Henny Youngman jokes to us, God bless him) ordered a chicken marsala that looked and smelled great. And the baskets of brown bread were tempting, though I resisted somehow.

I think we might go back to O'Leary's next week if we have a chance (at least for more pints). Is it worth getting the food there? Anyone been?

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  1. Costello's has pretty darn good burgers, but order them "medium rare on the rare side" or they can be overcooked.

    Never been to O'Leary's. How about a hound outing?

    2 Replies
    1. re: Bostonbob3

      Hmmm, I'm not sure how chow-ish O'Leary's is. It's dark, quiet, full of older funny Brookline guys, and is about as understated a place as you will find. If you looked up the word "Mistral" in the dictionary, you would probably find the word "O'Leary's" under antonyms,

      1. re: hiddenboston

        Yeah, but there's nothing more chowish than Henny Youngman jokes.

    2. I went to Costello's a few times a long time ago when they were just starting to offer full meals - Italian. I didn't like what I had. But maybe it's time to go back. After all, it's right in the hood. I actually like Galway House across the street. Cheap, mostly decent bar food.
      Speaking of Henny Youngman: A man goes to a psychiatrist. The doctor says “You’re crazy.” The man says, “I want a second opinion!” “Okay, you’re ugly too!”

      my blog:
      www.thegeminiweb.com

      4 Replies
      1. re: TheScribe

        I like the pub grub at Galway House ever once in a while, too. My only problem with the place is that it has an odd, flourescent glow that reminds me of Griffin's across from the Forest Hills T Station.

        And that place is just creepy.

        And yet I still go there on (drunken) occasions.

        1. re: TheScribe

          Hee hee! Last time I heard that joke, I laughed so hard I fell off my dinosaur!

          Costello's definitely isn't a destination place, but if you live near there, it's worth checking out again, if only for those chili cheese fries!

          1. re: hiddenboston

            One of my fav Henny Youngman jokes reminds me of Outback Steakhouse:

            "I know a man in Ft. Worth with 100,000 head of cattle. No bodies, just heads."

          2. re: TheScribe

            Costellos leases the kitchen. Changed a couple of years ago.

          3. O'Leary's had a solid, reliable burger that was less expensive than the Audubon's up the street, and nice, crispy fries, when I was living in the area 5-6 years ago. Friends who I ate with there who are still in the area tell me it hasn't changed a bit.

            2 Replies
            1. re: Notorious EMDB

              I think I might be heading back to O'Leary's next week sometime. Perhaps I'll give the burger a try, though the chicken marsala did look good, too!

              1. re: hiddenboston

                I used to live around the corner from O'Leary's and ate there often. Nearly everything on their menu is really good. My husband loves the fish and chips while I quite liked their small sirloin steak and their specials are pretty good. The brown bread is some of the most authentic you will find in Boston and they pull a decent pint.

            2. O'Leary's was hubby's regular lunch hangout when he was in grad school. I've been a few times, and remember the beef stew fondly. I also think we had a brunch there and there was a very good smoked salmon plate. It's a solid, nothing fancy, mellow place to eat and drink.

              1. I'm a semi-regular at the Galway. Its a great place to watch sports because they actually have the TV sound turned on, instead of music, like at Costello's. Although Costello's has better TVs. The kitchen at Costello's seems to change frequently. They used to have great pizza. The burgers are pretty good, but I like Galway's better.

                Anyway, recently the Galway has undergone some semi-renovation. In the dining room they stripped off the tacky paneling and painted the walls a weird taupe-type shade. I'm sure I'd call it an improvement. I don't know if this is the extent of the reno or if more extensive work is planned. But it seems the Galway is destined for yuppie-ization of some sort.

                I've walked by O'leary's many times after dinner at Sol Azteca or Chef Chiangs and it always seemed like a mellow attractive place for a beer or three. I'll have to check it out one of these days, for both food and beer.