🍇 Stomps, Sips, and Street Fests: Why Next Weekend on Long Island Might Be Better Than Your Vacation

September 5–7, 2025 | With Dean Miller, Your Neighborhood Insider

Look, I get it — Labor Day has come and gone, the pool floaties are deflated, and your inbox is full of emails with “Q4 goals” in the subject line. But if you think the fun’s over just because September showed up, let me stop you right there.

Next weekend, Long Island is still running during summer time — barefoot, wine-glass-in-hand, music-pumping, funnel-cake-eating summer time. So if you’re wondering how to spend your weekend, let’s walk through it like a true local (preferably with comfy shoes and stretchy pants).

Let’s kick things off Friday night, where North Fork vineyards are rolling out the barrels (literally) for Sunset Fridays. Starting around 5:30 PM, you’ll find live music, lawn seating, and wood-fired pizza trucks parked between rows of vines. If sipping Chardonnay while watching the sun dip behind the vines sounds too “bougie” — you’ve clearly never had that Chardonnay with garlic knots. It’s family-friendly, date-night-approved, and the golden hour selfies? Chef’s kiss.

Then Saturday rolls in, and things start to sparkle — literally. Sparkling Pointe is hosting its Chronicle Wine Cruise, which is basically a wine tasting, but on a boat. It sets sail from Greenport at 3:00 PM, and for two hours you’ll be gently rocking on the bay with bubbles in one hand and a cheese skewer in the other. If you’ve been dreaming of a moment that makes you say, “I needed this,” this is it. Just try not to post too many stories — you don’t want your friends texting, “Wow, must be nice.”

Now if boats aren’t your thing (maybe you’re still haunted by that fishing trip in ‘08), don’t worry — Saturday’s also bringing the party to Nassau County. The folks at The Langdon Social in Lynbrook are throwing a street festival from 12:00 to 5:00 PM, and it’s got all the essentials: local vendors, live music, great food, and people who say, “I’m just looking” while holding four tote bags. You might show up for a sandwich and leave with a handmade cutting board, a beaded bracelet, and a sudden urge to start your holiday shopping early.

Start your weekend off the right way (aka: tire the kids out early) at the No Matter What Foundation’s 5K Run/Walk over at Heckscher State Park on Saturday morning. It's a feel-good, do-good kind of event that supports mental health awareness — and yes, walkers are welcome. If your kid’s idea of cardio is running through Target’s toy aisle, this is a great way to sneak in some steps for a cause.

But let’s talk Sunday — and this one’s a biggie. Sparkling Pointe’s Stomp Party kicks off at noon, where you can actually stomp grapes with your bare feet like you’re auditioning for an old-school I Love Lucy episode. There’s live salsa music from Mambo Loco at 1:00 PM, and if you’ve never sipped rosé while dancing in a vineyard with grape juice between your toes… let’s just say you haven’t truly lived.

And just when you think the day’s peaked — surprise! — the Fizz & Fry pop-up starts at 3:00 PM. We’re talking sparkling wines paired with fried comfort food so good, you’ll wonder why anyone ever invented salad. Fried chicken with Brut? Fries with bubbly rosé? Yes, yes, and please stop asking — the answer is always yes.

So whether your vibe is sipping at sunset, stomping grapes with strangers, or jamming out at a street fair while eating a mozzarella stick the size of your arm, Long Island’s got you next weekend.

And hey, if weekends like this are making you think, “Why don’t we live closer to all this?”, you know where to find me. Whether it’s a move to the North Fork, downsizing in Nassau, or finally finding a backyard big enough for a grape stomp of your own — I’ll help you get there.

📲 Text me, call me, or wave me down at the next wine cruise. Just don’t spill your Prosecco.