The Jazz Age Lawn Festival is one of my favorite New York City Events.

First, there’s the obvious reason. When you’re obsessed with the 1920’s, it’s fun to be on an island surrounded by people who are, well, also obsessed with the 1920’s. You don’t have to feel weird or embarrassed about wanting to dress like a flapper or bootlegger, it’s encouraged!

But second, for all of the booze and crowds, people are genuinely really happy and friendly. I don’t know. Typically people get drunk at events like this and there’s fights, or everything becomes about getting a good shot for the ‘gram (guilty.) But something I definitely noticed at this event was how laid back it was and just how joyful everyone seemed.

Strangers were happy to make small talk. People were mindful of space and their manners. All sorts of people from all walks of life were welcomed without any weirdness. If Rick Steves were narrating this blog post, he’d say it was convivial.

If you normally skip events because of the drama and hassle that come with crowds, I get it. But I think you’ll find that the Jazz Age Lawn party has a different vibe entirely. HOWEVER, there’s a few caveats. There’s some things I definitely wish I knew before going, and so I’ll pass that knowledge onto you so that you can have a great time!

1.) Bring a Picnic

Does the event have food trucks? Sure. But do you want to spend most of your day standing around? No.

Eight percent of our day at the Jazz Age Lawn Festival was waiting in line for chicken tenders. We figured we’d start the day by treating ourselves to a bottle of wine, nothing wrong with that! But nobody had eaten breakfast, and wine…it kind of sneaks up on you. Food? Someone asked. Yeah…definitely food. Well, every food truck had an hours long wait. Ours personally kept us in line for three hours. There was even a fist fight ahead of us! We killed the time with a second bottle of wine…and then a third. There might have even been a fourth.

I looked around at the sea of people who planned well and was not only jealous, but impressed. I don’t know where the store is that apparently specializes in vintage picnic baskets, but everyone had one. Well, everyone except the five hundred people ahead of us on line for chicken and fries.

Those on their picnic blankets had bushels of grapes, gourmet cheese, whole rotisserie chicken, champagne, wine in fancy glasses, watermelon by the slice. Yeah, I couldn’t believe it either when people were pulling this shit out of their wicker baskets. My top tip would be to treat yo’ self and pack food.

2.) Bring Cash

It’s 2023 as I write this and I just want to know…WHY ARE WE STILL PAYING FOR THINGS IN CASH! I think we all know what it’s like to be caught off guard when we’re told that a business or restaurant only takes cash. Now imagine this nightmare scenario: Any line that you join for food or booze takes upwards of an hour. After waiting in the blistering sun or cold rain, you get to the front of the line only to be told they only take cash. How can things get worse? Oh, allow me! The only working ATM on the island doesn’t actually work because of random power outages!

Moral of the story? Bring cash. There’s a very real chance that you’re going to have a miserable time if you don’t. This isn’t like the rest of the city where you can just pop into a bodega and your biggest inconvenience is an ATM fee. You’re on an island and unless you have responsible friends with you who happen to have cash…you’re likely screwed.

The only upside is that if you ever wondered what the stock market crash felt like at the end of the Roaring Twenties, you’ll get a good sense if you show up sans wallet with cash.

3.) Get There Very Early

So I have social anxiety. Well, like, to be fair, I have all types of anxiety. All the anxieties possible, probably. The point is, I’m never someone who attends an event and says, “we’re leaving to go home already!?”

But the Jazz Age Lawn Party is one place where I definitely was upset when it was time to head back to the ferry.

There’s a lot of events that help you get immersed in the 1920’s theme. This is really what kind of makes the whole thing special. And these aren’t events that you can just do next weekend if you miss them. There’s Charleston lessons, croquet games, photos in the paper moon. You know, stuff that’s not typically offered out there in the real world. If you don’t give yourself enough time — you’ll miss these rarities. Get there early and give yourself plenty of time for it all!

4.) Prepare for all types of weather

It was hot. I was drunk. I was given a break from my child. I definitely made jokes that I shouldn’t have. Do yourself a favor and pack water. For most of the event, it was a scorcher. I don’t need to preach to grown people about the ways that water can help on a hot day.

Not to mention, if you faint from the heat on the mainland, someone calls an ambulance and you get some fluids and a high hospital bill. If you faint on Governor’s Island in front of hundreds of people…you can only imagine that chaos and shitty logistics of trying to get to a hospital. It’s embarrassing and inconvenient. Just bring a damn water bottle.

On the flip side, when it was time to go home it started raining and the air turned super cold. The ferry ride home was freezing (even though it’s a short trip.) A little jacket or fleece has never brought harm to anyone. I say bring one.

5.) People Go All Out

I get it, themed and costumed events as an adult are tricky, especially when it’s not Halloween. There’s always a very real chance that you’re going to go all out and people will say….what the hell is wrong with you? Can you relax?

But that’s not a reasonable fear here. People really love the 1920’s and with the event being on an island, people seem overjoyed to get lost in pretending that we’ve all time traveled back a few decades. As someone who gets a little self conscious to get into costume, I can confidently say that you’re going to feel more self conscious by not dressing up.

Both Amazon bought and homemade attempts at fitting the theme are welcomed, and you’ll notice that people really like seeing others dressed up. You’re sure to get smiles, compliments, and just good vibes for making the effort. This is one place in New York City where everyone isn’t competitive and scowling at each other. There’s a light-hearted sense of, dare I say, delight in the air. Unless you’re the guy from paragraph one who got into a fist fight over chicken tenders.

But I will say, bring comfortable shoes! There’s a lot of walking to get to and from where the actual party is happening. I wore a new pair of flats thinking, well they’re not heels, so I’ll be fine. Wrong. New flats + long walks = blisters. Break your shoes in before the event!

Another tip regarding this point, is please don’t be self conscious. Nobody is actively saying it, but it’s so obvious that every single person on that island is thoroughly enjoying pretending that they live in the Roaring Twenties. It doesn’t matter if you can’t Charleston — swing your hands around and move how you feel like moving. You’ll notice that everyone is doing the same — just moving in whatever way brings them happiness.