We’re in OB wrapping up the 2019 Vigilant Island Tour with our dear friends Kay and Steve. The first night was in Menemsha, so we ate at The Homeport. Saturday night we did Lobsters in Cuttyhunk and then we decided to hit the most touristy spot on Martha’s Vineyard for our third stop – Oak Bluffs.

I love Oak Bluffs in the spring and the fall, but haven’t been here in the summer due to the crowds. I added it to the end of this trip because the Harbormaster let me confirm a slip with a finger pier when I booked it last May. I also wanted to see how crazy it was in July.

When we first stayed here in 2017, we discovered The Red Cat Kitchen. Then in 2018, The Cardboard Box. Both are owned by Ben Deforest who recently opened a third – The Oyster Bar 02557.

When we visited in May, the site just had a “Coming Soon” sign out front, but now it’s opened, so I wanted to get inside and tell you all about it.

Unlike the Red Cat Kitchen, which feels like you’re dining in somebody’s cottage, or The Cardboard Box, which has a bit of an LA/South Beach feel, The Oyster Bar 02557 feels like a hip New England restaurant, definitely my pick of the three.

We arrived just before 6:00 on Sunday night and the place was fairly empty. That was okay with me since they don’t take reservations and everyone was pretty hungry.

Meanwhile people were lined up outside in front of the Fried Clam joint down the street. As we say in Mattapoisett “Summa People Summa not.”

I’m Finally A Pinot Guy!

Steve and I debated ordering single glasses of wine. I was going to go with the Annabella Cab and Steve was thinking Pinot. After a few seconds, I said “If you want to order a bottle of Pinot, I’ll have some.”

And with that I became a Pinot guy…

Steve ordered Four Graces and told me “I like the Oregon Pinots because they’re less sweet than the California varieties.” So now I have a place to start when I buy Pinots, I’ll start with Pinots from Oregon.

It’s All About The Oysters

As one might expect, Oysters are King here!

The Oyster Bar featured four local varieties. I spoke to shuckmaster (is that even a word), and he very accurately explained the characteristic of each. I’m a sucker for the large plump bad boys so he recommended Indian Cove from Onset.

Not only were they one of the best oysters I’ve ever tasted, they were perfectly accompanied by their house mingonette, which was so good that I almost drank what was left at the end.

The Food

Let me say at the outset that the quality of ingredients and preparation is totally consistent across all three of Ben’s restaurants. The reason to pick one over the other comes down to the menu and the atmosphere.

Of course, picking one by it’s menu is tough since they all change their menus on an almost daily basis. That said, of the three I felt like The Oyster Bar had more tempting offerings.

We began with the Onset Oysters and then ordered 4 rather different dishes with an eye towards sharing.

I continued my oyster theme with the Fried Oyster Appetizer ($19)…

This could have easily been an entree with a side of fries. Of course, the Oysters were plump and perfectly fried.

Steve ordered the Swordfish Special ($38).

It was perfectly composed and very fresh.

Mrs. Horne ordered the Lobster Orecchiette ($39). Both Kay and I had thought about ordering the same dish, but Mrs. Horne remembered how large the pasta portions were at The Cardboard Box and asked our server how big the Orecchiette was.

“It’s huge” she said and that’s when we decided to share!

It probably had a half a lobster in it. Mrs. Horne thought the sauce was a bit thin and Kay suggested adding more Parmesan. Our server brought a ramekin full of Reggiano and that did the trick – the dish was perfect.

Kay went with the Fish and Chips ($25)…

Kay freely shared the wonderful little shoestring fries, but no one else got a taste of the fish – as I said, everyone was hungry!

Our Server Taylor

Not only does Ben run great restaurants with dynamic menus, but he also seems to have a knack for hiring great people.


Taylor not only knew the menu inside and out, but was also very prompt, very helpful, and quite friendly!

As of today, The Oyster Bay 02557 stands as my favorite restaurant in Oak Bluffs…