What’s Going On Across Long Island this Weekend? (Oct 4–6, 2025)

Ah, October. The weather’s cooling down, pumpkin spice is everywhere (whether you like it or not), and Long Island is buzzing with weekend plans that don’t involve sitting in traffic in the Southern State. If you’re wondering what’s worth checking out next weekend, I’ve got your back — and no, it’s not just another open house list (although hey, if you’re in the market, I do know a guy…).

Let’s kick things off in Wantagh, where the one and only Mike DelGuidice is taking over Mulcahy’s Pub & Concert Hall on Saturday night. If the name rings a bell, it’s probably because he tours with Billy Joel and sounds more like Billy Joel than Billy Joel does. He hits the stage at 9PM, and trust me — this one sells out fast. Great music, great drinks, and probably someone in the crowd who went to high school with your cousin.

Looking for something a little more wholesome before the sun goes down? Head over to Miller Place for the annual Country Fair hosted by the Mount Sinai Historical Society. Think: handmade crafts, homemade jams, history buffs in colonial outfits (bless them), and your kids petting every goat they can get their hands on. It’s small-town nostalgia at its finest — and an excuse to eat funnel cake in the name of "supporting locals."

If you’re in a fall mood but also secretly love a good haunted vibe, you’ll want to swing by the Moonlight Market at the Suffolk County Farm in Yaphank. It kicks off at 4PM and runs till midnight, and it’s basically a night market with food trucks, vendors, live music, and just enough spooky energy to remind you that Halloween is creeping up. Bonus: you can shop under the stars while dodging corn maze jump scares.

Now, if you’ve got younger kids, the Touch-a-Truck Charity Toy Drive in Centereach is a home run. It's exactly what it sounds like — kids climbing in fire trucks, dump trucks, tractors — all while you sneak in coffee and people-watching. Bring a toy to donate, take some pictures, and enjoy the rare moment when your toddler is thrilled just to sit in the driver's seat of a garbage truck.

Sunday, don’t sleep on the Massapequa Park Street Fair. It’s packed with food, live music, and enough local vendors to keep your wallet busy. And if you’ve lived here long enough, there’s a good chance you’ll run into at least three people you know from high school or that one soccer team your kid was on in 2018.

So, whether you're in the mood to rock out, explore your inner colonial, chase fall vibes, or just walk the fair with a sausage-and-pepper hero in hand, Long Island’s got you covered next weekend.

Let Me Leave You With This:

Events like these? They’re part of what makes this place so special. It’s not just about square footage and kitchen islands — it’s about living somewhere that gives your family a reason to get out and make memories.

And hey, if you’re starting to wonder whether your current house is still the right fit… let’s talk. Whether you’re upsizing, downsizing, or downsouth-ing — I’m here to help you navigate it all (pumpkin spice latte optional, sarcasm guaranteed).