Dive bars in Boston

My wife is retiring and we decided to do a Boston dive bar trip in April. I was her bartender at a dive bar when we met and that’s our comfort zone so any thoughts from any of you who have been there? We are the early crowd and sit at the bar and talk up the bartender, they usually have a pretty good lay of the land for food, etc. Hotels that would put us in walking distance as well, suggestions are appreciated.

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Only went to Boston once but there’s a western bar across from Fenway called Loretta’s last call. Really good food and moonshine specials.

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Congrats on your wife’s retirement. Not sure about dive bars, but Boston was a very enjoyable trip for me and my wife when we visited not too many years ago.

Awesome Little Italy section in the city. Very walkable as well. Enjoy your trip.

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Just got flights and hotel booked. Staying at the “Verb”, flying direct out of Des Moines. OK I know how to stretch my dough. Round trip with seat assignments and checked bags is $148 or $296 for both of us. Used Travelzoo for the hotel, got 3 nights for $415.74, got a 3 night deal but to add Sunday would cost over $500 for the one night. Going to a Holiday Inn Express for day 1 and they have a free airport shuttle, should be just under $200 for Sunday night. So yes, I have to move after day 1 but que sera sera. So for roughly $1,000 after paying for transfers, we are going to spend 4 nights in Boston for 2 with air included. That opens the wallet up big time for food and libations.

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Went to Black Rose 25 years ago

Was a dive bar but has good chow and good vibe

I am sure it is still standing

An old place

Still there but not walkable from our location, right by Fenway.

Season 5 Yes GIF by Paramount+

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The Dugout

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Also a ways but will look into both.

Took the family out for an East Coast trip about six or seven years ago. Caught the tigers at Fenway Park and we surprisingly won that game. Did not hit any local bars though. Enjoy the trip brother.

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Congrats!

Bukowski Tavern… years ago

They will be playing the Tigers there 1 day after we leave. All good though because I’m less and less enamored with crowds these days. Red Sox are out of town while we are there which means that the neighborhood will be less crowded and I can hit the Bleacher Bar at Fenway and talk up the bartenders.

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The good… Who knew that it was the 250th Anniversary of “Patriot Day”…”In Massachusetts, Patriots’ Day in 2026 falls on Monday, April 20th, as it’s always the third Monday in April, commemorating the start of the Revolutionary War and also coinciding with the famous Boston Marathon and school vacation week. “ The Boston Marathon is on the 20th and we are 3 blocks away from the route.

The Bad…So we get in on the 19th but only had a room booked for the 20th thru the 23. I have been looking but had no idea of the urgency. Prices just went thru the roof yesterday and places are selling out quickly. I got a place under $300 today that is a 19 minute Uber from The Verb where we will be staying. I looked at adding a day at the Verb, it was over $500 originally then over $700 and then sold out in a few hours.

The Good…I’m finding dive bars that I am sure will be more than what I was looking for. Day 1, “12 Ben’s Tavern” in Southie. Then Bleacher Bar in Fenway Park Day 2.

The Bad…All those people in town for the Marathon are going to mean by 5 o’clock I’m probably headed back to the hotel. Looks like I’ll be bartending in our room for part of the trip.

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The Tam is a bit popular but I’d say it’s still a dive