Hay Bales, Bay Houses & Brass Bands: Here’s What’s Happening on Long Island This Weekend (Sept 27–29, 2025)

Hey there, Long Island neighbor —

You can feel it, right? The air is crisping up, your group chat is full of apple-picking memes, and suddenly every grocery store smells like cinnamon and pumpkins.

It’s fall. And Long Island is absolutely owning it this weekend with a full lineup of fairs, art, live music, and even a behind-the-scenes look at life on the bay. Whether you’ve got toddlers, teens, or you’re just a full-grown adult looking for something more fun than reorganizing your garage — this weekend’s got your name on it.

Let’s start with something totally unique: The Bay House Tours are back this Saturday and Sunday. This isn’t your typical house tour with granite countertops and walk-in closets. Nope — these are the historic, rustic bay houses off the shores of Freeport and Island Park. Built by fishermen and baymen generations ago, these homes are full of stories (and sea spray). It’s a chance to step off land and into the culture that shaped the South Shore. Plus, it’s probably the only time you’ll willingly put your phone away for hours and just listen to the water.

Now if you're more into land-based charm (and fewer boat shoes), head out east to Riverhead for the Hallockville Country Fair. We’re talking tractor parades, old-school butter churning, live folk music, and pies that might just change your life. This event is like stepping into a Norman Rockwell painting — minus the uncomfortable wooden shoes.

Or maybe you’re craving some art with a side of the sea breeze? Arts in the Plaza is taking over Kennedy Plaza in Long Beach this Saturday. It’s local artists, live acoustic music, and that unbeatable backdrop of the boardwalk just steps away. Bring a coffee, wear your comfy sneakers, and consider picking up a piece for your hallway wall — even if it’s just so your guests stop commenting on how “bare” it feels.

Speaking of art and antiques — the Southold Historical Museum is hosting their Autumn Antiques, Fine Art, and Crafts Fair all weekend long. It’s perfect for those who appreciate hand-carved furniture, vintage finds, and the kind of pottery you pretend you’ll use but will 100% end up displaying on a shelf like museum treasure. It's peaceful, it's charming, and it's way more satisfying than scrolling Amazon at midnight.

And for those of you who want a bit of everything — food, culture, music, and a good reason to not do yardwork — the Outdoor Art Show & Music Festival in Setauket is calling your name. Local musicians will set the soundtrack while artists and vendors line the Village Green with color and creativity. It’s family-friendly, low pressure, and just the kind of outing where you accidentally spend three hours and don’t regret a second.

Does Your Home Fit Your Life Right Now?

Whether you're in the middle of soccer season chaos, dreaming of a quieter place with more trees and fewer taxes, or just realized your home doesn’t work for the way you actually live — maybe this is the season to talk about change.

I’m not just here for fall events and local tips. I’m here to help you make sense of the market, get smart about your next move, and finally find the home that works for you — not the other way around.