Hottest Spot on North Shore

Visit Carson City Saloon
Two Dollar Sundays
Follow us on Twitter
Hemingways Pittsburgh



photos map Darts Pool table Smoke-Free Rated 6
403 Semple Street
Pittsburgh, PA 15213
P: 412-682-3060

Sports Restaurant Local Hangout College

Games: Pool - 2 Tables, Darts, Arcade Games
Music: Metal, Alternative, Rock, 90s, 80s, 70s

Bar Hours

Mon. - Sat.10:00amtil2:00am
Dance floor
Look & Feel
Bar Size
Dance Floor Size
Dining Size
Bottled Beers
Draft Beers
Mixed Drinks
Frozen Drinks

Beverage Prices

Beer Types Domestic Import
Draft Beer Draft $1.00 N/A
Draft Beer Bottles $1.75 $2.25
Draft Beer Pitchers $5.00 N/A
Beer Notes:  Guinness on tap!
Frozen Soda Mixed Shot




Mixed Drinks




Review Staff Review: 8

Review Staff Review: 8

By: Nathaniel Beall

Bootlegger's is a new Oakland establishment that sits on the site of the old S.O.D. Bar. This one-time favorite college hangout for Pitt students has new owners and is really putting a lot into cleaning up it's image. The most amazing thing is that the prices are still pretty cheap. There wasn't too much of a crowd there when I showed up for the review but it was cold out and early on a Wednesday night. The people who were present were a really nice mix that crossed all social borders. One thing I noticed is that the new owners really care about fixing the place up and that they had even gone so far as to close off the very abused downstairs bathroom area. To some this may be considered a crime since there was graffiti on the walls ranging back to the 60's. If you find yourself in Oakland, and you are looking for a good place with cheap drinks, you can't do much better then Bootleggers.

Weekly Specials, Happy Hours & Events

Weekly Specials, Happy Hours & Events

Monday Specials & Events No Cover

Yuengling Bottles $1.50 9-11.

Tuesday Specials & Events No Cover

$2.00 Import Night, Including Guinness Draft 9-11pm.

Wednesday Specials & Events No Cover

$4 Pitchers 9-11pm.

Thursday Specials & Events No Cover

$4 Miller, Miller Lite, And Mgd Pitchers 9-11pm.

12 Wings For $3.75.

Friday Specials & Events No Cover

$1.25 Miller. Miller Lite, And Mgd Bottles 9-11pm.

Saturday Specials & Events No Cover

$1 Well Drinks 9-11pm.

User Reviews Average User Rating: 7.3

User Reviews Average User Rating: 7.3

By: TarynNicole - Mar 05 2015 @ 10:02 AM

User's Rating: 7

Bootleggers is a typical college bar in the heart of Oakland. The interior space has a relaxed and laid back vibe and is usually dimly lit but with not much d├ęcor to speak of. The only space apart from the bar area is a billiard room with three pool tables and a place to play darts. Very unique and interesting murals on the walls of the billiard room! The staff is always polite and work hard to serve everyone in a timely manner but with only bartenders no servers on a weekend it can take a hot minute to get waited on.

The drinks are between a 6-8 rating, they usually have decent pitcher specials and the mixed drinks aren't low on liquor. Six packs are available for purchase too. The atmosphere is a nice setting to catch up with friends or play a game of pool and large TV's are posted around the bar to watch whatever games are on. Overall, I've enjoyed this bar multiple times without waiting in a long line outside on the weekends and would recommend it to others. I plan on returning and give this typical college town bar a seven overall.

By: Alavella - Mar 02 2015 @ 11:31 AM

User's Rating: 9

This bar is great... if you love dive bars. As far as Oakland is concerned this bar is rarely ever crowded. This is the bar you go to if you want to be able to sit down, have a drink, and not be surrounded by drunk college kids. The drink specials are extremely cheap compared the surrounding bars. The only disadvantage is that they allow smoking in there all day long, so most of the time you leave with a particular scent. The bartenders are very nice and always up for a conversation if you are willing to talk to them. There is also a back room with a dart board and pool tables.

By: L.o.l.a. - Sep 21 2012 @ 03:52 PM

User's Rating: 7

Significant improvement made recently! Bootleggers was alright for the drinks and to hang out but now that they renovated it is significatly better. Moved up on the list of bars to hit up in Oakland.

By: Monte - Mar 28 2010 @ 04:49 PM

User's Rating: 8

Ok...First's cheap!!! Dirt, on a college budget,... cheap!!! And opposed to what the barsmart website says, their is a dance floor. I know this first hand because I dj there on Fridays. And there were 50 people doing the Cupid Shuffle in front of my stage area. Which also has a stripper pole on it. ;) only gripe was when it got busy, the bartender on break decided to hang with her friends instead of hurrying back to work. Listen, maybe they are on a schedule. But I waited 20 minutes and only got my beer when I asked for a beer and coke. So my gripe is ....Understaffed! Terribly. Jami and Lyndsi did fine bartending, and definitely, definitely are good to look at without being slutty.
There's a pool table in the back, bathroom is small, but adequate. And though the BarSmart review says it was dirty, I have to disagree. It is very clean. The crowd was great.

By: Keigu07 - Mar 15 2009 @ 03:34 PM

User's Rating: 2

A couple of friends and I went here for a couple of drinks, but the bartenders were so drunk that we could not get served. We tried many times to get their attention, but they were so focused on the people that they knew that they wouldn't even acknowledge us. I really don't recommend this bar anytime.

By: Arich9504 - Apr 01 2008 @ 12:52 AM

User's Rating: 9

Bootleggers is the BEST bar in Oakland. On top of that, it is easily the best sports bar in Oakland. During Steelers & Penguins games you will generally find a pretty good crowd there to watch the game. So throw on your Crosby or Roethlisberger jersey and come on down!

You'll get a very mixed crowd at Boots, but always a fun and friendly one. Most people i know there live within a few blocks of the bar, and seeing as how it's S.Oakland mostly everyone is early-mid 20's, except for Hippie Mike, but everybody loves him.

The drinks are priced very well, which is good, because you'll want to put the rest of your money into tipping the bartenders. They are absolutely BEAUTIFUL! Amy, Amara, Danyelle, Stephanie, Jamie(sp?) love em all...

If you play pool or darts there are generally some pretty good shooters at Boots, i just may be one of them, bring it on.

I frequent this bar more than any other in da Burgh, if i didn't like it i sure as hell wouldn't keep going back multiple times a week!

By: Sbb11578 - Apr 02 2001 @ 01:24 PM

User's Rating: 9
Hopped in there one night just for something different. Lots of stuff happening. Loved the big screen tv. Cheap beer. Excellent cross breed of folks. Everyone from Grandpa to Jill celebrating her 21st to lesbians to girls just trying to hide from frat boys. Good time by all. Good bartenders too.
Local Events
29 30 31 1 2 3 4
5 6 7 8 9 10 11
12 13 14 15 16 17 18
19 20 21 22 23 24 25
26 27 28 29 30 31 1
Visit Carson City Saloon Two Dollar Sundays Follow us on Twitter Hemingways Pittsburgh