The Bar
From Homestar Runner Wiki
The Bar has appeared in a few different toons. It seems to always feature Cold Ones or 'old ones and a bowl of peanuts on the table. It has a dartboard and a LEMKE pennant on the wall. Stairs are visible through one door, so it might be in a basement, or it might have a second story. It serves as the meeting place for the Broternal Order of Different Helmets.
Its second Flash appearance in Summer Short Shorts was almost identical to its first in the Theme Song Video, with an updated look to the bar and the characters.
In the DVD commentaries for Summer Short Shorts and Ever and More, the Brothers Chaps suggest that the bar is in Pom Pom's basement, referring to it as his "rumpus room".