The Hester Street Fair: NYC’s Cultural Market You Didn’t Know About

Matthew Loyd

September 23, 2019

Last weekend, a couple of friends and I headed into Manhattan for the Hester Street Fair’s Vintage day, which turned out to be full of nice people, nice clothing pieces, and a really laid back atmosphere. Not many New Yorkers are familiar with the Hester Street Fair events; you could even walk by on the street and miss it if you’re not paying attention.

What is the Hester Street Fair?

“Founded in 2010 by three Lower East Side locals, the Hester Street Fair has set the standard for what a market is, while transcending the notion and meaning of a typical “food court” or “flea” to become a one-of-a-kind curious, cultural and community gathering, drawing from the diversity of the neighborhood and New York City at large.”

This is the description provided on the Hester Street Fair website, and it describes the event very well. The Hester Street Fair resides down on the Lower East Side of Manhattan, on the crossroad of Hester and Essex street in Seward Park. Every weekend during the summer and fall they have events ranging from New York City style OktoberFest celebrations, to private fashion shows, and ,more famously, flea markets. The Hester Street Fair has done much in the way of giving local small businesses a platform to engage the community by hosting them as special guests or vendors at their stellar events. Tons of local visual artists, musicians, streetwear brands, and food vendors, have had the opportunity to promote their brand on a more public level. The Saturday before last, I grabbed a camera and headed down to the street fair for their Vintage Day. As a first timer to this wonderful event, I wanted to document my experience.

Now, this is much more than just your typical flea market, and this has helped the Hester Street Fair solidify its spot in the Lower East Side for almost a decade. Each event has a theme, and the activities, vendors, and businesses that occupy Seward Park revolve around that in some fashion. As aforementioned, I went on their Vintage Day event, and the park was turned into an active clothing market. The park was filled with vendors selling vintage streetwear and fashion pieces, as well as jewelry and other odds and ends like VHS tapes and even CBD capsules.

The outfits were on point too, everything from people rocking the newest Sacai x Nike collab to stylish business casual plaid blazers and the like. There was music by DJ Ella Hussle and Lala & Radiohead, and that coupled with the smell of fresh cooked food gave the nice chill vibe of an outdoor summer barbecue.

After walking around and taking in the bustling atmosphere, and seeing the various vendors’ wares, I thought it was high time I made a purchase myself. I sifted through the racks of vintage tees and jackets, and boxes and bins of old hats, referencing things like 90s TV shows and movies, sports teams, and music groups. The one thing I must say about “vintage” clothing is that it is usually pretty overpriced, and unfortunately that is largely in part due to the “vintage” tagline. A trend about half a decade in the making, popularized by celebrities like Kanye West and Shia LeBouf (who popularly stylized vintage rock imagery and fashion), the whole idea of “vintage” and the vintage aesthetic has become extremely popular and has grown beyond the typical “rock band tour t-shirt” bubble from which it started. A friend of mine saw a dope Final Fantasy shirt that he liked, and ended up not buying it because a vendor was charging over $100 for it. Asking prices for old caps ended up being around $20, which is much more modest. However, a new one of better quality and material could easily be purchased today for the same price or $5-$10 more. However, I have to applaud these vendors though, people will buy into the “vintage” trend, so a lot of times, you can ask what you want. And I don’t mention all this to say that the prices for things were totally unfair, as there were a decent amount of steals and fairly priced items, but you have to make sure to really look and not only grab the flashiest item at a tent.

I ended up buying two items that afternoon. I bought a ring from a jewelry vendor for $25. It’s a plain, metal ring with a large flat bar over the finger, and I will admit, I kind of regretted paying $25 for it. To me, it wasn’t worth $25 as the metal wasn’t anything super extravagant. But I redeemed myself and got a GREAT price on a pair of Nautica nylon track pants from another vendor. They were going for $40 (which is a great price for any pair of pants) and they had this really nice burnt orange color to them. I really like nylon track pants because they give an awesome 90s look, and they’re especially comfortable. They’re a bit big (size XL, a medium to large would’ve fit me well), but they have drawstring fasteners to be tightened around the waist, and I like my clothes a bit over-sized anyway. I haven’t worn them yet but I’m excited to see what outfits I can pull off with them.

Overall, the Hester Street Fair was an awesome experience, and I definitely plan on going back again. This past weekend they had their regular Saturday market, with a focus on vegan food and highlighting smaller vegan food businesses. If you check out their site,, you can see the upcoming events they have for the following weekends, one of which is an upcoming Octoberfest on the 5th of October. Maybe we’ll run into each other there, but even if we don’t, you should definitely stroll on by one weekend and check it out before it’s done for the season. It’s a free and fun thing to check out in NYC, and I am positive you’ll be glad you did!