After a long week Jack and I were driving through Western Massachusetts when we got a hankering for some diner food.  We asked our navigation computer where the nearest diner was, and it sent us to the Yankee Diner in Charlton, MA.  As you can see from Jack’s face, we were so excited to eat there.  Jack’s Nana had eaten there years ago and she thought it was really good.  But as the car pulled into what had once been the Yankee’s parking lot we discovered the sad truth: that even the best diners sometimes die.  This is why I’ve been trying so hard to make sure that Jack visits as many classic diners as possible.  Some day they may all be gone, and I’ll be forced to find some other obsession to drag my children to see.

We knew that Charlie’s was just down the road (having been there the previous Sunday), but it closes early these days.  We asked the computer to find us another diner in the area but there just weren’t any to be found.  By this point Jack was getting antsy, and Deena (did I mention that Deena was with us?) just wanted to find someplace to eat.  So with total sadness we drove to the nearest shopping mall and ate at an Applebees.

Can you imagine the let down Jack and I felt?  It was like heading to Fenway Park, only to end up at Tropicana Stadium.  I’d like to say that I enjoyed my meal but it tasted like ashes in my mouth.  I had wanted to give my boy a new diner experience, and I had failed him.  Thankfully, as always, he was a good sport about the whole thing. We eventually reached Deena’s folks’ house and went to bed.  Early the next morning I said goodbye to Jack, Winston the Dog, and the Maletz clan, and headed out for my short business trip.  As I wound through the back roads of Duchess and Putnam Counties it occurred to me that before the trip was over I might be able to take Jack to great diner that neither of us had ever eaten at.

A short story: back in September, on the day Carly Roz Robinson was born, my buddies Dane and Pete and I were heading for a meeting in NJ.  We were set to meet up with two other friends on the highway.  Thinking we had some free time, we decided to stop for breakfast.  Getting off of I-84 we stumbled upon this unusual looking diner called Bob’s in Brewster, NY.  We sat down, placed our order, and then suddenly got the call.  Our friends had arrived at our meeting spot, and we had to bolt.  We sadly explained to our waitress that we had to cancel the order and ran out the door.  I swore that I would get back to Bob’s, and take Jack with me.

Well, on this freezing cold Saturday morning Jack was running around his grandparents’ house torturing his dog, but I wanted to eat at Bob’s.  I punched up the request in my GPS and discovered that it was just 4 miles away.  With the excitement I used to reserve for Phish concerts and dates with Deena I drove to Brewster.  And there it was.  It’s really not much to look at from the outside.  No fancy architecture.  No chrome or neon.  Not even fancy sign.  But like so many things in life, it’s what’s on the inside that makes Bob’s special. 

I came in during the end of the morning rush and sat down at the counter.  Ten seats long, with a view of the grill.  I recognized my waitress from my last trip, and said hello.  She brought me steaming hot coffee and a glass of water.  I ordered an omelet filled with veggies, home fries, a stack of white toast, and a side of bacon.

You’d think that from diner to diner there wouldn’t be much of a difference between omelets.  Or hash browns.  Or coffee, for that matter.  And you’d be wrong.  Watching him work, I saw first-hand how much care and attention Tom, the owner and grill master, seems to put in his food.  Most cooks throw their potatoes and onions on the grill and leave them until the rest of the order it finished.  From my seat I watched over and over again as he carefully stirred the hashbrowns, insuring that each batch was cooked evenly. The ingredients were all fresh, too: you could see in my omelet that the mushrooms were hand cut, and not from a can.  So were the other vegetables. You could taste each element in each bite, whereas a lesser omelet leaves the overcooked innards in an almost tasteless paste. Another diner trick is to cook all of the bacon ahead of time, and then warm up a couple of pieces when they are ordered.  As I saw him lay down the raw strips on the grittle I knew that mine would be fresh and tasty.  And they were, with just the right blend of saltiness.  My meal was absolutely delicious. 

But the food is only part of the reason I now call Tom’s my favorite diner in New York State.  The atmosphere of this place is FANTASTIC.  Never before have I met such friendly, welcoming – and pretty – waitresses in a diner.  I highly recommend sitting at the counter, if only to watch the show that they put on for the customers.  Nicole and Emma, who have been working there for 5 and 3 years, respectively, act like sisters.  They argue, they call each other names, and they purposely get in each other’s way.  They eat each other’s food during break time.  Sometimes they actually get physical with each other, as you can see in this photo.  It’s all in fun, and they clearly do love each other.  But it’s also part of the charm of Bob’s.  It feels like one big, somewhat dysfunctional, family. 

While I was there I met a bunch of the regulars.  They all seemed genuinely interested in this quest that Jack and I are on, and even mentioned some other local diners that we should try (more on that in the future).  Everyone seemed to know each other’s names.  I bought myself a t-shirt, paid my bill, and thanked everyone for a wonderful time.  I announced that I’d be back the next day with Jack.

And 24 hours later the Tootieman and I were back, with Deena and her parents as well.  We took a booth in the back, since Jack isn’t old enough to sit on a stool without falling over (I cannot tell you how much I look forward to him being ready for that!).  The day before Nicole had told me to try the corned beef hash, which was made fresh by Tom each day.  So I ordered that and some toast.  Jack got his standard scrambled eggs.  Deena and Gail got French toast, and Steve got fried eggs and potatoes, along with wheat toast. 

Now I have to be honest that both Gail and Deena felt that their French toast wasn’t hot enough.  And Gail had been hoping for some type of homemade hot cereal.  Maybe the next time we’re there these things will be different.  But we still loved our trip, and the food was just as good as the day before.  Tom’s hash is simply the best that I’ve ever tasted (even better than the 4 Sisters Owl in Lowell, MA).  Jack loved his eggs, and enjoyed showing off his new trick of drinking milk through a straw.  Cressie, our waitress, took great care of us. 

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I just love this place.  It’s open until 10pm weeknights, and 24 hours on the weekends.  I look forward to trying Tom’s other culinary delights, and taking Jack to see our friends at Bob’s.  It truly is a special diner. 

Bob's Diner
27 Main St
Brewster, NY