Y'know, a while back, I had a cheesesteak sandwich from another place in Pittsfield that I thought was pretty bland because they were more focused on doing what was "proper" than what is "pleasurable". Old Man Jeff's Pittsfield Brisket Cheese Steak with Fries gets it right! Everything about this sandwich is better than the "typical" because of the amount of creativity put into it that is designed for you to enjoy eating it! The bread is a good balance of soft and crispy. The brisket is tender and well-seasoned. The sauce tastes delicious and unique, and flavors the entire sandwich. I got mine with peppers, onions, and jalapeños, and I recommend it to anyone. It's also pretty large, and comes with what I think may very well be the best fries in the city. I also ordered Brisket Egg Rolls and Pulled Pork Egg Roll, which are pretty substantial and packed with flavor, and come with creative dipping sauces. I also enjoyed the savory pickles. Absolutely the best BBQ joint in Pittsfield!
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Anthony T
Local Expert • 69 contributions
Loved
• 26/01/25
• DoorDash order
Hands down the best BBQ restaurant in Pittsfield. The Smash Burger alone is probably the best burger I've had in a long time, and I most likely will stick with this place when I need a burger from now on. I also got the BBQ Pu Pu Boat to sample the other vittles on the menu, and it did not disappoint! I lived in the south for 20 years... Pittsfield more than gives anything I had there a run for its money with Old Man Jeff around! 5/5
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Gina C
5 contributions
Loved
• 12/06/25
• DoorDash order
Everything was delicious. My pancakes were a little on the darker side but the blueberries are fresh and massive so i assume it's because it had to be cooked all the way through, the Mac & Cheese was better than I expected and the cornbread alone is good and filling!! I would eat this everyday if I could.
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Young P
10 contributions
Loved
• 27/02/25
• DoorDash order
everything was on point the Brisket Egg Rolls surprised me was delicious tho and the Burnt Ends Super Spud forget about it innmy Italian voice lol top notch only thing i would say is they need to expand the doordash menu thats all my only gripe i would say besides that the food is on point !!!
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Carol N
Emerging Expert • 36 contributions
Liked
• 01/07/25
• DoorDash order
I had to try the brisket Pittsfield Brisket Cheese Steak with Fries. Unfortunately the bread was so wet it fell apart. Maybe heartier bread that's toasted. I had to remove the brisket & couldn't eat as sandwich. The brisket was very tasty. I found no evidence of any cheese. Still, great food here.
