Editor’s Note: I really have to thank the guys at REI in Redwood City for recommending this fantastic establishment to Alex and I. Without them, we would never have known to venture into downtown San Mateo for a good burger.
Jeffrey’s Hamburgers has that all-too-predictable 50′s diner theme that you find with many mediocre restaurants (like Mel’s and Lori’s), but don’t write them off just yet. Yes, there are silly red vinyl chairs and silver tables, with a limited burgers/fries/milkshakes menu, but Jeffrey’s offers much more than your average burger joint.
It was your average Sunday night, after a long hike at Half Moon Bay and a quick stop at REI when Alex and I decided to check out Jeffrey’s Hamburgers. We were exhausted, famished, and on a frantic hunt for some heavy food, so when we were recommended to a place where there were “killer burgers and shakes”, we were in.
Alex didn’t even take a minute to look at the menu when he quickly decided on a bacon cheeseburger and eagerly waited while I debated on fries vs. onion rings and burger vs. grilled cheese. I eventually settled on a grilled cheese after I spotted one on the grill and saw how melty and oozey it was when it was sliced in half. As far as the sides went, Alex and I decided to share chili cheese fries and a mint chocolate milkshake.

Clockwise from top left: Bacon cheeseburger, Kid's mint chocolate shake, chili cheese fries, grilled cheese
What began as a starved race to get food in our systems, quickly became a slow-paced tasting you’d expect from a fine restaurant. The burger was crisp and charred to perfection while the in-house ground beef remained juicy and perfectly pink. All of the burgers are served plain and dry, inviting you to visit the condiment bar to load up on any toppings and sauce you prefer. The grilled cheese instantly took me back to my childhood and they surprisingly had the perfect touch (not too much) of butter and simple American cheese.
And then there were the sides. We almost threw our arms up in surrender when we tasted their hearty chili that was made creamy with the melted shredded cheese. It was a pretty simple chili (tomato paste, pinto beans, ground beef, green peppers, onions) but the natural depth of all the flavors cooking together (probably all day) were such a tasty match with the crisp medium-thick french fries. The milkshake was the perfect classic finish to our meal. We basically fought over who got to hold it in the car as we both wanted to have as much as possible.
We have since been to Jeffrey’s quite a few times and are now well aware that 2 shakes are necessary for an agreeable ride home.
