Back in the 1990's there were three reigning kings of pit beef in Baltimore, (Chaps Pit Beef, Big Al's and Big Fat Daddy's) but now much has changed. Pit beef joints come and go, and you can find them listed at Yelp left and right.
BEST TO EAT AT
Chaps pit beef is the only one left of the original big three, their stand and eat in shack still located on the same seedy corridor of Route 40 Pulaski Highway outside the Gentlemen's Gold Club (which is a fancy way of saying boobie bar). You can go and dine and enjoy their food at 5801 Pulaski Highway and you wont walk away hungry. See more about them or their menu here. City Paper was a big fan of this place, hey, it is in the City. They've also been on Diners, Drive-in's and Dives and on the Food Network so if you are looking for a juicy pit beef for lunch, go here. When I'm hankering for a pit beef, I go there and can barely finish the large size sandwich, side of fries and drink. It's moist, meaty, and delicious. If you are having a small party or just don't feel like cooking they have party platters you can pick up too. Gift cards are a great idea for someone you know in the Baltimore area. It's worth stopping in and taking some photos just because they are still there. You can verify their hours at their website or by calling them at 410-483-2379.
BEST FOR CATERING
Now if you are looking to get pit beef for big company event, (event over 100 people) check out Big Fat Daddy's who still does catering in the Baltimore area if you can get a date booked. They were in the NY Times, Saveur Magazine, and catered for NFL Linebacker Ray Lewis twice, so you decide. I saw a blurb in the June 2010 Rachael Ray Grilling issue they were best pit beef in Baltimore (Catering) in 2010 by Rachael Ray Magazine which again is testament. They are not the cheapest but they set up a several hour all you can eat three buffet in your backyard or company parking lot and all you can eat means just that. If you want a full tummy and food that you will remember for the rest of your life this is them. Companies should know discounted rates for middle of the week events apply so do ask. They have moved operations to Pennsylvania and you can't eat there but you can find them up and down the East Coast at BBQ Events, fairs or festivals. See their website or call them at 410-908-9241
That doesn't mean you still can't look around for the best pit beef, which could now be housed outside baltimore. Small places are cropping up day and night and if they can survive, they may earn the title. Baltimore is comprised of Baltimore County and Baltimore City so leave no stone untouched.