🎯 Long Island Weekend Survival Guide: May 31 – June 1, 2025

Expert-backed, sarcasm-laced, crowd-pleasing edition

Ah yes—another glorious Long Island weekend approaches. The forecast? 50% chance of sunshine, 50% chance of beach traffic, and a 100% chance you’ll say “we should do this more often” at least twice.

You’ve got options—more than your cousin’s excuses for missing your birthday BBQ. From pickle-powered pet festivals to flower shows fancier than your niece's Sweet 16, we scoured the Island so you don’t have to. You’re welcome.


🐾 Pickles & Paws

📍 Southaven County Park, Yaphank
🕒 Saturday, May 31 · 11:00 AM – 5:00 PM

This pet-friendly festival is a paw-some event for animal lovers! Bring your furry friends and enjoy artisan vendors, tasty food, and family-friendly activities, all in the lush surroundings of Southaven County Park.

Expert Tip: Arrive early for shaded parking—and if your dog wears booties, prepare for side-eyes and photo ops.


🌸 Long Island Orchid Festival

📍 Planting Fields Arboretum, Oyster Bay
🕒 May 30 – June 1 · 9:00 AM – 5:00 PM

Take in the beauty of exotic orchid displays and learn from gardening experts during this three-day floral celebration set in one of Long Island’s most picturesque gardens. 

Expert Tip: Bring your DSLR or at least clean your phone camera. Flower pics only hit if they’re high-def.


🎨 LIC Springs! 2025

📍 Vernon Blvd, Long Island City
🕒 Saturday, May 31 · 12:00 PM – 5:00 PM

This community street fair brings together local performers, artists, and small businesses for an afternoon of family-friendly fun, fitness demos, and cultural showcases. 

Expert Tip: Wear walking shoes. “Cute but comfy” is your mantra. You’ll thank us when you’re 12 blocks in.


⚓ HarborFest Dock Day & Craft Fair

📍 Port Washington Town Dock
🕒 Sunday, June 1 · 10:00 AM – 5:00 PM

Celebrate Port Washington’s maritime heritage with boat rides, handmade crafts, live music, and fun activities for the kids—all set against scenic harbor views.

Expert Tip: Bring cash. Craft vendors and Square readers don’t always get along.


🎭 Mosaic Festival

📍 East End Arts, Riverhead
🕒 Sunday, June 1 · 12:00 PM – 5:00 PM

This colorful cultural festival showcases diverse traditions through music, dance, visual arts, and cuisine. A must-attend for anyone who values community and creativity! 

Expert Tip: Sample the food early before the lines form—this isn’t your average street fair pretzel scene.


🎶 Luke Bryan Concert

📍 Jones Beach Theater
🕒 Saturday, May 31 (Evening)

Country fans, rejoice! Luke Bryan is taking the stage at the legendary Jones Beach Theater. Expect high-energy performances and plenty of summer anthems under the stars. 

Expert Tip: Pre-game responsibly in the parking lot, then walk in like the country royalty you pretend to be.


🎤 Comedy Karaoke Night

📍 First Presbyterian Church, Greenlawn
🕒 Saturday, May 31 · 5:00 PM – 8:00 PM

Looking for a good laugh? Enjoy stand-up comedy followed by an open karaoke session—great for a casual night out with friends. 

Expert Tip: Go early, sign up fast, and remember: no one’s ever nailed Celine Dion. Don’t try.


🛍️ Westbury Street Fair

📍 Downtown Westbury
🕒 Saturday, May 31 · 10:00 AM – 4:00 PM

Explore a lively mix of local artisans, food vendors, and community exhibits at this all-day street fair. A perfect way to support the locals while enjoying great eats and entertainment.

Expert Tip: Hit the booths in reverse. Everyone starts at the front.


🍎 Long Beach Farmers Market

📍 Kennedy Plaza, Long Beach
🕒 Saturday, May 31 · 9:00 AM – 2:00 PM

Pick up fresh produce, baked goods, and crafts by the beach. This market blends the charm of small-town shopping with oceanfront relaxation.

Expert Tip: Get there before 11 AM for the best produce and least judgment from kombucha vendors.


🏃‍♀️ Great South Bay YMCA 5K Run/Walk

📍 Bay Shore
🕒 Saturday, May 31 · 8:30 AM

Start your weekend with a heart-healthy run or walk in support of community fitness programs. All ages and experience levels are welcome. 

Expert Tip: Skip the cotton tee. Go moisture-wicking or go home (sweaty).


🧘 Wellness Day at Village Square

📍 Glen Cove
🕒 Saturday, May 31 · 9:00 AM – 12:00 PM

Join local health and wellness vendors for a rejuvenating morning of yoga, fitness demos, and holistic health resources. 

Expert Tip: Don’t skip the vendors. You might discover your new favorite crystal or CBD balm.


🏛️ Joseph Lloyd Manor Tours

📍 Huntington
🕒 Saturday, May 31 · 11:00 AM – 3:00 PM
History buffs will love this guided tour through one of Long Island’s oldest manors. Discover its role in American history and admire the preserved architecture and gardens.

Expert Tip: Ask the guide about Jupiter Hammon—the first published African-American poet. Impress your friends later.


🚨 Weekend Market Pulse (Because We’re Fancy Like That)

  • Local tourism is up 12% YOY. You staying in town is actually trendy.

  • Farmers markets are booming—hyperlocal is the new Whole Foods.

  • Live music & festivals are outperforming traditional events. Translation? Your social calendar > Netflix.


🎤 Final Rant—I Mean, Thoughts

So if you’re still saying, “There’s nothing to do on Long Island,” maybe check your Wi-Fi. This weekend’s lineup is stacked. From quirky festivals to historic deep dives, it’s time to stop doomscrolling and start living.

🗣️ CALLING ALL ISLANDERS:

📸 Post it.
🚗 Drive there.
🍻 Meet someone new.
🎟️ Pick one thing, show up, and stop ghosting your social life.

And hey—when you’re Instagramming your weekend with a Montauk brew in one hand and your dog in the other, don’t forget to tag us.

#WeekendWarriorLI #LongIslandLife #SeeYouOutThere