🗓️ What’s Happening on Long Island This Weekend?

Nov 1–2, 2025 | By Dean Miller, Real Estate Guy Who Knows Where the Fun Is

Let’s be honest — Halloween is over, but your kids are still sneaking candy like they’re in a sugar heist movie. You’re one “fun-size” Snickers away from hiding the bowl in the attic. So what do you do to balance out the candy chaos?

You go out. You explore Long Island. You live a little before the turkey shows up and eats the rest of November.

Here’s what’s worth your time this weekend — and no, it’s not just craft fairs (although... there are a few).


Let’s kick things off with something smooth — and no, not your leftover pumpkin-spice creamer. I’m talking about Gail Storm Live at the Jamesport Meeting House on Saturday night. This local legend brings jazz and blues vibes to one of the oldest, most charming venues on the North Fork. It’s intimate, relaxed, and the kind of night where you leave saying, “Why don’t we do stuff like this more often?” If you’ve got a sitter and a taste for live music, this is a no-brainer.

Now if live music isn’t your scene and your weekend motto is “shop, sip, repeat,” then you need to head to the Free Craft Fair Weekend at The Shoppes at East Wind in Wading River. It’s going on both Saturday and Sunday and it’s exactly what you need to pretend you’ve started holiday shopping (even if you leave with nothing but candles and kettle corn). There are local vendors, seasonal goodies, and let’s be honest — it’s also just a nice excuse to browse while sipping cider and people-watching.

But maybe you're in the mood for something a bit more… dazzling. Cue the 2025 Winter Gala at the Long Island Museum in Stony Brook on Saturday night. It’s a full-on, grown-up event — dinner, dancing, dressed-up people who definitely ironed their clothes. If your idea of a wild night includes hors d'oeuvres and supporting the arts, this is your chance to break out the good 

And if you’re more of a foodie, Sunday also marks the start of Fall Long Island Restaurant Week. It runs all week, and it’s basically a cheat code for dining out. Prix-fixe menus at some of the Island’s top spots, so you can have that three-course meal without hearing your wallet cry. Pro tip: make a reservation. These tables go fast — especially when dessert’s involved.

Last but not least, for all my early bird holiday shoppers out there, the Southold American Legion Craft Fair on Sunday offers everything from handmade gifts to knitted things you didn’t know you needed until now. Plus, it’s Southold — beautiful drive, good food nearby, and small-town charm that’ll make you feel like you're in a Hallmark movie… with better coffee.


🏡 P.S. — If These Events Make You Crave a New Kind of Weekend Life…

If you’re reading this and thinking, “We really should be living closer to this stuff,” you’re not alone.

These are the weekends that remind you what Long Island life can look like — community, fun, walkable towns, and homes where hosting a dinner party doesn’t require folding chairs from your garage.

Whether you’re looking to upsize, downsize, or just make a smart move before year-end, I’ve got the inside scoop on where the market’s headed — and where your next chapter could begin.

📲 Let’s connect: 516-984-3286
🌐 Or browse a few homes in between events: www.TheBeaconTeam.com

Enjoy the weekend — and if you buy a candle you don’t need, just know I did too.