🎷🎨 Sip, Stroll, Repeat: Your Long Island Weekend Starts Here

August 15–17, 2025

You know those weekends where everything just lines up? The weather’s great, the events are actually worth putting pants on for, and the kids are (relatively) cooperative? This might be one of those weekends — but only if you plan it right.

Luckily for you, I already did the heavy lifting.

Here’s what’s worth leaving the house for this weekend across Long Island — whether you’re craving live jazz, a glass of local wine, a little vintage fashion history, or a good old-fashioned punk rock show.


Let’s start class. Friday night, you can head out to Wainscott for an evening that sounds like it came out of a romance novel: the Camille Thurman Quintet is performing live at LTV Studios as part of Hamptons JazzFest. Imagine this — warm summer air, the smooth hum of a saxophone, and just enough rhythm to justify that sway you break out when no one's looking. The show runs from 7:30 to 8:30 PM, so you've got time for dinner before or drinks after. If you’ve never done a jazz night out east, this is your moment.

Not your tempo? No problem.

Over in St. James, the Atelier at Flowerfield is hosting a stunning Long Island Landscapes art exhibit, showcasing the work of two incredibly talented local artists — Patricia Yantz and Jonathan Van Brunt. It’s open all weekend, 10:00 AM to 4:00 PM, and it's the kind of peaceful cultural reset we could all use before diving back into emails and baseball practice. Plus, let’s be real: it gives off serious “I do cultured things” energy without needing to fake your way through a modern art explanation.

Now, if you’re the type who hears “drive-in movie” and instantly smells popcorn, you’re going to love this. On Friday night at 8:00 PM, Harmony Vineyards is hosting its “Drink in Theater” series — a cozy outdoor movie night where the wine is poured, the stars are out, and the vibe is pure laid-back luxury. I don’t know what they’re screening yet, but let’s be honest… even if it’s an ad for dryer lint, the view, the wine, and the people-watching would still make it worth the trip.

On the historic side of things, swing over to Sag Harbor to catch the wildly underrated exhibit “When Women Wore Whales” at the Whaling Museum. Open all weekend from 10:00 AM to 4:00 PM, this one dives into the bizarre-but-true world of 1800s fashion — where, yes, actual whale bones were used to shape corsets. I don’t recommend trying that at home, but I do recommend bringing the kids. It’s weird enough to keep them interested and educational enough to feel like a parenting win.

Speaking of weird, wonderful, and absolutely worth it — on Saturday, August 16, the Long Island Pride Pop-Up Festival takes over Kennedy Plaza in Long Beach from 12:00 PM to 6:00 PM. Expect rainbow everything, drag performances, music, food trucks, local vendors, and the kind of joyful, welcoming atmosphere that makes you wish every day was Pride. It’s family-friendly, high-energy, and honestly just a blast — even if you’re not usually a festival person.

Oh, and if you’re more into power chords than pride flags, you’re not forgotten. The local punk and hardcore scene is still very much alive and shredding at places like Amityville Music Hall, with shows running all weekend. You’ll hear it before you see it. If you need to release some stress, lose your voice for a good reason, or just miss the feeling of being 19 in a mosh pit — go. Just maybe don’t wear white shoes.


🎯 Dean’s Quick Weekend Strategy:

  • Friday Night: Art exhibit stroll or vineyard movie date — your call.

  • Saturday: Hit Long Beach for Pride, then dinner by the boardwalk.

  • Sunday: Chill out with jazz replays on Spotify, or relive the 19th century with whale-boned corsets and homemade root beer in Sag Harbor.


🏡 And one last thought...

If your current home doesn’t feel like it fits weekends like this — whether you’re dreaming of a bigger backyard, more space for entertaining, or easier access to vineyards and beach towns — let’s talk. I help people not just buy homes, but build lives they actually want to live in.

📲 DM me, text me, email me — whatever works. I’m here to help you enjoy this weekend and the 52 others every year.