Your Long Island Weekend Planner: Festivals, Food & Family Fun

Ultimate Weekend Planner + Expert Tips for Every Event

Long Island is bursting with life this weekend, with an exciting mix of festivals, art, live performances, and food experiences. Whether you’re a lifelong local or just exploring for the weekend, this guide will help you discover what’s happening and how to make the most of it.

Here's your event-by-event breakdown, complete with pro tips from local insiders.


🎭 FEATURED FESTIVALS & FAMILY EVENTS

🦸‍♂️ Cradle-Con: Comic, Collectible & Pop Culture Convention

📍 Cradle of Aviation Museum, Garden City
🕙 Saturday & Sunday, May 17–18 | 10 AM–5 PM
🎟️ Tickets: $25 adults | $15 kids
💬 Long Island's top fan gathering for comics, cosplay, collectibles, and celebrity panels.

🧠 Expert Tips:

  • Bring a backpack for purchases and snacks—food lines can get long.

  • Arrive before 10 AM for best parking and early access to limited-edition merch.

  • Don’t be shy—cosplay contests are beginner-friendly and super fun!


🐑 Fleece & Fiber Festival

📍 Hallockville Museum Farm, Riverhead
🕙 Saturday, May 17 | 10 AM–4 PM
🎟️ Free
💬 A heritage celebration featuring live sheep shearing, artisan crafts, and hands-on demonstrations.

🧠 Expert Tips:

  • Come early for full shearing demos (they may wrap up early afternoon).

  • Wear farm-appropriate footwear—dirt paths and grassy areas are common.

  • Looking for a quiet moment? The barn exhibits are less crowded midday.


🐚 Babylon Clam Fest

📍 Salt Shack Seaside Grill, Cedar Beach
🕚 Saturday, May 17 | 11 AM–6 PM
🎟️ Free entry; food for purchase
💬 Seafood favorites, beach games, and live coastal music—all with a perfect ocean view.

🧠 Expert Tips:

  • Hit the seafood booths before 1 PM for freshest selection.

  • Bring sunglasses, hats, and towels—the beach location is exposed to full sun.

  • Use public beach lots early or carpool—Cedar Beach fills fast on event days.



🐴 Equestrian Festival – Long Island Horsemen’s Association

📍 Muttontown Preserve, East Norwich
🕦 Saturday, May 17 | 11:30 AM–4:30 PM
🎟️ $10 per vehicle
💬Equestrian shows, pony rides, petting zoos, and scenic walking trails.

🧠 Expert Tips:

  • Wear walking shoes—you’ll cover a lot of ground between zones.

  • Ideal for photographers: sunset light over the preserve is stunning.

  • Early slots for pony rides tend to be shorter lines.



🎭 CULTURE & ENTERTAINMENT

💃 42nd Street – The Musical

📍 The Gateway Playhouse, Bellport
🕗 Saturday & Sunday, May 17–18 | Showtimes vary
🎟️ $39–$69
💬 Broadway-quality theater in a charming village venue. Expect stunning tap choreography and feel-good storytelling.

🧠 Expert Tips:

  • Dinner and a show? Book at local favorites like Porters on the Lane or Peter’s on the Green before the curtain.

  • Matinees are family-friendly and less crowded.


🗺️ Fixed in Time & Place – Historic Map Exhibit

📍 Sag Harbor Whaling & Historical Museum, Sag Harbor
🕙 Saturday & Sunday, May 17–18 | 10 AM–4 PM
🎟️ $5 admission
💬 Trace the history of the East End through rare maps and historic documents.

🧠 Expert Tips:

  • Sag Harbor is walkable—park once and explore the nearby marina and shops.

  • Ask museum staff about interactive elements for kids.


🏃 HEALTH & WELLNESS

👟 AMP Summer Shred 5K Run/Walk

📍 AMP Personal Training, Syosset
🕣 Saturday, May 17 | 8:30 AM
🎟️ $30–$45 includes t-shirt and post-race goodies
💬 Get a morning workout and support community fitness initiatives.

🧠 Expert Tips:

  • Check-in opens at 7:30—use this time to stretch and warm up.

  • Stick around for vendor raffles and health product samples post-race.


🥗 FARM-TO-TABLE EXPERIENCE

🌿 Spring Menu to Savor – Art of Eating

📍 Art of Eating, Bridgehampton
🕚 Saturday & Sunday, May 17–18 | 11 AM–5 PM
🎟️ Reservations required
💬 A curated tasting experience featuring seasonal ingredients and elegant outdoor seating.

🧠 Expert Tips:

  • Book ahead for garden seating—it’s their most scenic spot.

  • Their lemon-thyme chicken and spring vegetable salad are chef favorites.


📌 WEEKEND SUCCESS CHECKLIST

Plan Transportation: Many events offer free parking, but beach and park venues fill early.
Pack Smart: Reusable water bottles, hand wipes, sunscreen, and small bills for cash-only vendors.
Look for Local Specials: Many nearby cafés and boutiques offer event-day discounts—ask around.
Check Social Pages: Instagram and Facebook pages often post real-time updates, cancellations, or weather changes.
Be Present: It’s not just about checking off activities—make time to enjoy the atmosphere and meet locals.


📝 Final Thoughts

Whether you're dancing to live music by the beach, diving into pop culture at Cradle-Con, or sipping spring cocktails in Bridgehampton, this weekend on Long Island has something unforgettable waiting for you.

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