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Wicked Good Guides / Boston Dives / Historical dives /

Essex Street

The Playland closed a couple of years ago (sniff), but before it did it was the oldest continually operating gay (and a little bit more)bar in Boston, having opened, I belive, in 1938. The building is still there as it is a historical site. Ask anyone who has ever been there and they'll probably groan, but smile at the same time. Everyone has a playland story.(and everyone knew- arrive in a cab/leave in a cab) A true dive. X-mas lights 365; cheap drinks/smoky air; regulars, bartenders, and a waitress, who all looked ten minutes late for their dirt nap; a jukebox playing only suicidal/songs/by/dead/divas (Judy Garland, Patsy Cline...); drag queens bursting out of the bathroom screaming "That mothahfuckah stole my fuckin' cocaine"; and best of all, a sign over the bar that read: BANKS DON'T SERVE LIQUOR; WE DON'T LEND OUT MONEY -- Charlie


My God! Your description of Playland is exactly as I remember it! But....sure had some good times there!

Posted by Drex on May 21, 2004 09:27 PM

It's so easy to tell when someone tries to review a long-gone institution like Playland Cafe even though they obviously never went there. It opened in 1937 and closed in 1998. Having worked there for 10 years (the best in my 33-year career, so far), your synopsis is a load of crap. If you don't know about a place -- simply ask someone who ACTUALLY WENT THERE! The piano bar, the Thanksgiving dinners (started in 1942), the holiday raffles benefitting the hospice at Mission Hill. 8 a.m. openings for the third shift people (many were regulars), the hookers, the hustlers as well as the doctors and lawyers (yes we had quite a few professionals -- ALL professions). It was a place that will never be duplicated and will always be missed by those who actually went there regularly. Sadly, many who worked there as well as the owner (one of the finest men I've ever known -- and the most noble gentleman I've ever worked for) have passed away. BUT the joyous memories live on! God bless Playland and all who sailed through her!

Posted by Michael R. on March 29, 2005 09:33 PM

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