1. Eastport Summer Festival
When: Saturday, June 21st at 4 PM
Where: Main Street, Montauk Street, Eastport, NY
Welcome the start of the season with the Eastport Chamber of Commerce's annual Summer Festival on Main Street! Join us for a vibrant, family-friendly celebration that showcases artisan vendors offering unique crafts, delectable local food and beverages, and live music to set the festive mood. Held in the heart of our historic hamlet, this event promises a day filled with community spirit, entertainment, and plenty of opportunities to enjoy the summer sunshine. Don't miss out on this exciting kickoff to the season in Eastport!
2. 2025 Islip Chamber of Commerce Street Fair
When: Sunday, June 22nd at 11 AM
Where: Main Street, 517 Main Street from South Bay Ave to Smith Ave., Islip, NY 11751
Get ready to kick off summer in style at The Islip Summer Kickoff on Main Street! Happening Sunday, June 22 from 11 AM to 6 PM, this beloved annual tradition is once again taking over Main Street—from South Bay Avenue to Smith Avenue—for a day packed with fun, food, and festivities. Hosted by the Islip Chamber of Commerce, the fair features a GIANT Craft & Vendor Bazaar with unique creations and must-have finds, a MAGNIFICENT Kids FunZone with inflatables and obstacle courses courtesy of NY Party Works, and the mouthwatering LI Bites Food Truck Rumble with 12 of Long Island’s best trucks serving everything from BBQ to tropical drinks. Don’t miss live music by Souls on Board and the perfect excuse to stroll, shop, and savor all that downtown Islip has to offer!
3. Midsummer Nights
When: Jun 20, 2025 through Jun 22, 2025 (daily)
Where: Old Westbury Gardens, 71 Old Westbury Road, Old Westbury, NY
Celebrate the longest nights of the year with an enchanting evening at the Gardens, where guests of all ages are invited to picnic, stroll, and unwind in a beautifully illuminated setting. Lanterns will light the pathways, while wreaths and floral arrangements add a festive touch to the serene landscape. Bring your own picnic or enjoy delicious offerings from Cafe in the Woods, operated by Polka Dot Poundcake of Rockville Centre. All ticket sales are final. In the event of inclement weather, guests are welcome to attend on Friday, Saturday, or Sunday, and will also receive complimentary general admission tickets.
4. Long Island FunFest
When: Jun 20, 2025 through Jun 22, 2025 (daily)
Where: Suffolk County Community College, 485 Wicks Road, Brentwood, NY
Long Island's largest fair is back and better than ever, bringing unforgettable fun for the whole family! Enjoy first-class entertainment, thrilling midway rides and games for all ages, mouthwatering fair food, and a spectacular Saturday night Fireworks show by Grucci. Your admission includes free access to incredible attractions like the heart-pounding Globe of Death and aerial feats from Circus Murcia, the Big Bee Transforming Robot Car, a jaw-dropping BMX Freestyle Stunt Show, the thrilling Dinosaur Experience, and an educational petting zoo that's perfect for kids. Don't miss this action-packed celebration!
5. Hope Is Here 5K Run
When: Saturday, June 21st at 9 AM
Where: First Responders Memorial Park and Ball Field, 1121 Old Nichols Road, Islandia, NY
Join us for the Hope Is Here 5K Run/Walk/Stroller-Walk with Kid's Fun Run, a meaningful event dedicated to raising awareness of parental mental health. Presented by the Postpartum Resource Center of New York and the Village of Islandia, this family-friendly day supports New York State moms, dads, and families at risk for or experiencing perinatal mood and anxiety disorders, including postpartum depression. Together, we aim to increase education, screening, and access to treatment, while offering support programs and training for healthcare providers and community members. Be a part of this important mission to empower parents and build stronger, healthier communities through compassion, connection, and care.
6. Sunset Yoga (All Levels)
When: Sunday, June 22nd at 6 PM
Where: Sunken Meadow State Park, 1 Sunken Meadow Parkway, Kings Park, NY
Join us for a peaceful evening of yoga and connection as we find balance together while watching the beautiful sunset. This all-levels session welcomes everyone in a supportive, non-judgmental environment. We'll meet by the catering hall on the left-hand side of the beach. Please bring a yoga mat or towel, some positive energy, and a $10 exchange fee. See you there!
7. Family Fun Weekend at The Shoppes
When: Jun 21, 2025 through Jun 22, 2025 (daily)
Where: The Shoppes at East Wind, 5720 Route 25A, Wading River, NY
Join us for FAMILY FUN WEEKEND at The Shoppes at East Wind on Saturday and Sunday, June 21 & 22, 2025, from 11 AM to 5 PM, as we kick off summer with two exciting days of family-friendly activities and entertainment! Sponsored in part by Renewal by Andersen and NY Life Long Island, this festive event features live music from local favorites including the Newfield High School Drum Ensemble, Sweet Ride, and Emy McB. Kids will love our free face painting, bounce house, and special meet & greets with beloved children’s characters—including a certain favorite blue pup! Explore a real fire truck and learn about fire safety with the Wading River Fire Department at our Touch-a-Truck experience. Enjoy tasty treats, shop family-focused vendors, and don’t miss Paddock Simworks racing simulators—Sunday only in the parking lot. And of course, take a spin on our iconic Grand Carousel. It’s the perfect way to celebrate the season together!