Winfield Street Coffee

Hello everybody!

I am still experiencing some writers block, so I took some inspiration on what to write about from my dad, who suggested that I write about a place I have already been to a few times this year: Winfield Street Coffee! 

As its name suggests, it’s a chain of coffee shops in Connecticut, New York, and Florida. Okay, that’s not what its name suggests at all. In fact, some of you who are reading this probably thought it was a coffee shop that is located on Winfield Street in some town or city. But no, it’s a chain that has six locations. Two in New York City, two in Naples, Florida, and the two locations that I have been to, Rye, New York and Stamford, Connecticut.

The story of this place actually goes all the way back to 1925, when Winfield Delicatessen first opened in Norwalk, Connecticut, and quickly became a beloved neighborhood staple. 

In 2015, a man named Breno Donatti, who came from Brazil to America at the age of 18 years old and had worked his way up in the world of jobs in food service, found himself taking over that struggling location in East Norwalk. 

From 2016 to 2019, the brand ended up expanding its reach, opening locations in both Westport, Connecticut and Stamford, Connecticut. The former is no longer open, while as I have already said, the latter is still open. Its plans to expand their reach were put on hold in 2020 due to the pandemic, but they got back into it from 2021 to 2023, as it is when they expanded beyond Connecticut and opened kiosks at subway platforms on the Upper East Side of Manhattan, and two other locations in Naples, Florida. 

In 2025, they had a very big year, as after seven years of negotiations with the MTA, including running a successful three-month pop-up shop in Spring 2023 to test the local market, they opened their biggest location inside the historic Rye Metro-North Station House, which is not only a coffee shop, it also serves craft cocktails and has outdoor seating, as well as a ton of tables and TVs on the wall.

There is also a surprisingly extensive menu there, as not only do they have many different options for Coffee, they actually have full menus for Breakfast and Lunch, which I didn’t even notice during any of the four times I went there. I only just found out about it as I have been writing about it, and I first saw it on the website, and I had to do additional research to see if the menu was exclusive to certain locations, and once I found that it was also the menu at the Stamford and Rye locations, I felt that I had to include it. 

The first interesting dish they have is a Toasted Ham & Cheese Croissant Sandwich.

The next dish they have is a Chicken Parmesan Sandwich with Chicken Cutlet, Provolone, Parmesan, Marinara, and Hoagie Roll.

The next dish they have is a Melt with Cheddar, Provolone, American Sourdough, and it can also come with Tomato Soup.

The next dish they have is a Sandwich with Fried Chicken Cutlet, Bacon, Hot Peppers, Swiss Cheese, Honey Mustard, and New York Roll. 

The next dish they have is a Cuban Sandwich with Roasted Pork, Ham, Swiss Cheese, Pickles, Dijon Mustard, and Hoagie Roll.

The last interesting dish they have is a Pecan Fried Chicken Wrap with Pecan Crusted Chicken, Oranges, Avocado, Toasted Almonds, Romaine, and Honey Mustard Vinaigrette.

There actually are more foods on their menu, but none of them seem interesting to me, so I am not going to mention any of them. 

Now, as someone who has been to both the Stamford and Rye locations twice this year, you would probably think that I have a favorite location of the two. And I actually do in fact, and the answer might surprise you. It’s the Rye location, and it’s simply because it is bigger and less crowded. Yes, as much as I love Stamford, the location there is just tucked off to the side of The Ferguson Library, making it get very crowded at times. 

So, now that I have talked about this place as much as I can, I know what you’re all thinking: Why have I been here more than once this year? Those two locations are not in my town, or the next town over. And I don’t even drink coffee. And I only just learned about their menu while I was writing this blog post. So, why would I go to a coffee shop that has two locations near me that are both 30 minutes from where I live, when I don’t drink Coffee and only just learned about their menu? Well, I’ll tell you why. 

My close friend Emily has been holding worship and prayer events at both the Stamford and Rye locations, and as I’m sure you all know, it means a lot to me to get to see my friends. Yes, the reason why I have even been here in the first place, and why I am writing about it now, is because my friend held her events here. And I am truly grateful for it, not just because I got to see my friend and got introduced to her friends, but because in just this one blog post, I learned way more about the fascinating history of Winfield Street Coffee than I ever thought I would. I had no idea it goes all the way back to the 1920s, and that it was a long process to open its location in Rye.

Overall, this is a way more fascinating place than I thought it was. If you ever want to check it out, head over to Rye or Stamford! And thank you, again, to my amazing friend Emily, for introducing me to this place, and for being part of the reason why this blog post exists!