Your Long Island Weekender: Top Events, Festivals & Family Fun, Friday, Sept. 19 – Sunday, Sept. 21, 2025
LONG ISLAND, NY – As summer begins to fade and the first hints of fall creep onto Long Island, the weekend ahead is packed with festivals, live music, and outdoor fun. Whether you’re looking to enjoy a community celebration, catch a big concert, or cheer on athletes at Jones Beach, there’s something happening in nearly every corner of the Island.
From Greenlawn’s beloved Pickle Festival to high-energy tribute bands at Westbury, plus a major IRONMAN competition on the South Shore, this weekend is full of opportunities to get out and experience the best Long Island has to offer. Here’s your guide to what’s happening Friday through Sunday.
Festivals & Community Celebrations
- 45th Annual Pickle Festival
Saturday, Sept. 20 • 10:00 AM – 4:00 PM • John Gardiner Farm, Greenlawn – A Long Island classic, the Pickle Festival offers pickles of every variety, hayrides, crafts, and live entertainment. Fun for families and foodies alike. - Unity Fest (New Location!)
Saturday, Sept. 20 • 2:00 PM – 9:00 PM • 21+ – Celebrate with live music, vendors, food, and more in a festive atmosphere. Great for adults looking for a Saturday out with friends.
Music & Nightlife
- PBR: Camping World Team Series
Friday, Sept. 19 • 7:45 PM • UBS Arena, Elmont – Professional bull riding comes to Long Island with all the energy and spectacle of a rodeo, plus live entertainment. - 80s vs. 90s Night featuring Decadia & DJ Savage
Saturday, Sept. 20 • Evening • Mulcahy’s, Wantagh – Throw on your neon and denim for a dance-worthy clash of decades at one of Long Island’s most popular nightlife spots. - The Ultimate Doors: Tribute to The Doors
Saturday, Sept. 20 • 8:00 PM • Flagstar at Westbury Music Fair – Relive the spirit of Jim Morrison and The Doors with this authentic tribute performance. - Killer Queen — A Tribute to Queen (ft. Patrick Myers as Freddie Mercury)
Sunday, Sept. 21 • 7:30 PM • Flagstar at Westbury Music Fair – End the weekend with a powerhouse Queen tribute, complete with all the big anthems.
Outdoors & Family Fun
- Northwell IRONMAN 70.3 New York
Saturday, Sept. 20 • Jones Beach – Thousands of athletes converge on Long Island’s iconic shoreline for the IRONMAN 70.3 triathlon, a grueling test of swimming, biking, and running. Spectators welcome! - Hoedown Throwdown at 89 North
Friday, Sept. 19 • Patchogue – Country vibes hit Patchogue with live music, dancing, and plenty of fun to kick off the weekend.
Quick Snapshot
| Day | Notable Event(s) |
|---|---|
| Fri, Sept 19 | PBR Team Series at UBS Arena; Hoedown Throwdown in Patchogue |
| Sat, Sept 20 | Pickle Festival; Unity Fest; 80s vs. 90s Night; Doors Tribute; IRONMAN 70.3 |
| Sun, Sept 21 | Killer Queen Tribute at Westbury |
Hidden Gems
Nature Trails – With cooler weather arriving, it’s an ideal weekend to hike Caleb Smith State Park in Smithtown or Sands Point Preserve on the North Shore.
Local Breweries & Tasting Rooms – If you’re near Riverhead or Patchogue, many breweries host special weekend tastings and small live acts.
Farmers’ Markets – September brings some of the best produce of the season. Look for farmers’ markets in Huntington, Northport, and Port Jefferson on Saturday mornings.
