Long Island’s Not Boring This Weekend. You Might Just Be Tired.

August 8–10, 2025 | The Official Weekend Game Plan (No Babysitter Required)

Look, I get it. It’s August. You’ve done the BBQ circuit. The beach towels are still sandy from two weekends ago. And your kids are bouncing off the walls like they’re rehearsing for American Ninja Warrior: Home Edition.

But before you default to another weekend of “let’s just stay in,” hear me out — Long Island is absolutely stacked this weekend. We’re talking nostalgia, sea creatures, local wine, and life history with people dressed like it's 1842 (and somehow pulling it off). Here's how to max out your weekend without maxing out your patience.

🎮 First up: The LI Retro Gaming Expo.

At the Cradle of Aviation Museum in Garden City, the Expo kicks off Friday afternoon and runs through Sunday. If you ever yelled at your sibling over Mario Kart or swore that Duck Hunt “cheated,” this is your jam. Classic arcade machines, rare collectibles, cosplay contests, and enough button-mashing to wear out your thumbs — this is not just for the kids.

Pro tip: go early, bring snacks, and pretend you're “just there for the kids” while secretly trying to beat your personal best on Street Fighter II.

🎬 Then slide over to the Long Island Music & Entertainment Hall of Fame in Stony Brook.

They’re hosting a weekend-long film festival with music documentaries, Q&As, and a whole lot of “Hey, I didn’t know that person was from Long Island!” moments. It’s air-conditioned, culturally enriching, and located in one of the most charming villages on the island — which means coffee, boutiques, and a solid excuse to sneak in a pastry from Crazy Beans.

🐠 Want something more kid-centric? Hit the Long Island Aquarium in Riverhead.

From shark feedings to jellyfish tunnels and penguin meet-and-greets, this place is a surefire way to make the kids happy and convince yourself you're winning at parenting. Plus, you’re five minutes from the Riverhead Ciderhouse — where adults can unwind with a hard cider flight while the kids devour cider doughnuts like they’re going out of style.

👒 Feeling fancy (but not Hamptons fancy)?

Spend your Sunday out East at one of the North Fork’s stunning wineries. Macari, Wölffer, Raphael — they’re all pouring, all picturesque, and some are even kid-friendly. That’s right: you can sip cab franc while your kids chase butterflies and eat Goldfish crackers in the grass. It’s called balance.

Just make a reservation, and please — don’t be the people who bring a speaker and blast music at 1 PM. We’re trying to keep it classy, not crashy.

🏡 And for the slower-paced, screen-free crew?

Old Bethpage Village Restoration is where it’s at. It's like stepping into a time machine that smells faintly of fresh bread and chimney smoke. With costumed reenactors, horse-drawn wagons, and old-school candy at the general store, it’s the closest you’ll get to the 1800s without giving up your air conditioning. Great for kids, oddly relaxing for adults, and a total curveball from your usual “park and playground” routine.

Dean’s Final Thoughts:

This isn’t the weekend to stay home and wonder why your kids are bored or why your spouse keeps Googling “getaways near NYC.” Everything you’re craving — connection, fun, peace, and a little novelty — it’s already here. On Long Island. In your backyard.

And if reading this made you realize your current backyard isn’t quite cutting it anymore — let’s talk. I’ll help you find a home where weekends like this feel just right.