Long Island's Greatest Summer Festivals and Events You Won't Miss

Summer on Long Island isn't all about dodging the LIE or competing for Robert Moses parking space—summer is the season the island flaunts its stuff. From classic music festivals, to offbeat boat races, to strawberry shortcake aplenty to consume as much as you're presumably allowed by law, 2025's festival season is going to be hot, loud, and packed—and well-worth it.

Your slightly snarky, hyper-local, fact-checked guide to the summer activities you *really* need to attend

Alive After Five – Patchogue Village

The reigning champion of Main Street takeovers, Alive After Five in Patchogue is still the summer block party you've always dreamed about. Live music? Check. Food vendors? Naturally. Beer? Certainly. But the 2025 spin? Even more sustainability vendors, higher-end food truck fare, and yes, the return of the iconically abrasive grilled corn vendor. Arrive early to park in the vicinity of your ZIP code.

The Great South Bay Music Festival – Shorefront Park, Patchogue

Returning for its 17th iteration, the four-day genre-hopping music festival features more than 60 acts on the Shorefront during July. There’s indie favas playing along with reggae legends. For 2025: A wellness tent, because why not?, and VIP packages that may actually be worth the money. It’s crazy, incredible, and thoroughly Long Island. Just stay hydrated—you’re no longer 22.

Port Jefferson Dragon Boat Race Festival – Harbor front Park

Underrated and well worth the time. Expect fast boats, team camaraderie, cultural performances, and an A-plus food court. Racing or just basking in the energy of the waterfront, the September event is low-cost and high-reward—and unexpectedly photogenic. So pack the camera and the competitive spirit.

Mattituck Strawberry Festival – North Fork

It's sweet. It's sticky. It's complete nostalgia. The June Strawberry Festival offers sugar spikes and small-town charm. 2025 features extended hours, increased live music, and (at long last) an actual kids' area that doesn't feel like a temporary installation. Insider tip: Friday night is residents' night—head out then, avoid the Saturday bedlam.

Long Island Summer Festival – Stony Brook

This July institution gets that all elusive family/kind-sorta-leaving-the-guys-behind-in-the-beer-garden balance just right. You'll find well over 100 local vendors, several food truck lanes, and an adoption booth for pets that will put your emotional fortitude to the test. And: shade. Well, thank the heavens for shade.

Riverhead Cardboard Boat Race – Peconic Riverfront

Who knew seeing cardboard boats go belly-up could be so rewarding? Every summer, residents construct homemade floatation fiascoes and race to win glory, pride, and the unofficial award for “Most Dramatic Capsize.” It's strange. It's ridiculous. It's the pinnacle of Long Island, and you should definitely go.

Oyster Festival – Theodore Roosevelt Park, Oyster Bay

Okay, technically in October, but stretching “summer” because that’s how good this event is. The Oyster Festival is a gastronomic blowout with bivalves aplenty, along with rides, vendors, and live music. 2025’s feature? A new oyster-shucking speed competition. Yes, as intense (and sloppy) as it sounds.

Blue Point Brewery Summer Concert Series – Patchogue

Craft brew and live music? Don't be surprised. Blue Point Brewery brings weekend concerts all summer with a changing schedule of local musicians, summer seasonal, and grub vendors who are pros at the grill. Tip: Get there early—there are only so many seats and spots of shade.

East End Seaport Maritime Festival – Greenport

If you've ever dreamed of watching an actual whaleboat race and munching on lobster rolls and browsing nautical antiques, consider yourself lucky—this is the day. Over the middle of September, the Maritime Festival serves up history, harbor scenery, and an air of preppy appeal that's tough to top.

Levittown Fire Department Festival – Levittown

Occasionally all you need is carnival rides, cotton candy, and that one thrill ride that certainly shouldn't be allowed in three states. The Levittown FD festival has just that—and fireworks, live music, and an unbeatable retro atmosphere. Come for the nostalgia, and you'll stay for the funnel cake food coma.

Want to Experience the Real Long Island This Summer—Without Missing a Beat (or a Boat Race)? 

Whether you're a lifelong local or fresh to the scene, Long Island’s summer events are calling—and you’ll need more than just SPF and Instagram to keep up.

DM me or drop a comment for your exclusive 2025 Festival Survival Guide—including where to park, what to eat, and how to avoid standing in the wrong line for 45 minutes. Let’s make this your best Long Island summer yet. 🌊🍓🎶

See you at the corn stand—I'll be holding iced coffee and high expectations.