1. Mother's Day Brunch at Windows on the Lake
When: Sunday, May 10th
Where: Windows on the Lake, 235 Lake Shore Road, Lake Ronkonkoma, NY
Celebrate Mom with a beautiful Mother’s Day Brunch at Windows On The Lake on May 10, 2026! Gather your family and friends for a delicious brunch featuring an array of desserts, unlimited mimosas, a sundae bar, and stunning waterfront views. Capture special memories with family photos available on-site and enjoy a relaxing afternoon dedicated to Mom’s special day. Reserve your table today — parties of 8 or more will receive a complimentary bottle of wine. Maximum seating time is 2 hours per table.
2. Bald Hill Fair
When: May 9 - 10
Where: Catholic Health Amphitheater at Bald Hill, 1 Ski Run Lane, Farmingville, NY
Kick off fair season on Long Island with an unforgettable weekend of family fun, thrilling entertainment, and spectacular fireworks by Fireworks by Grucci lighting up the sky both Saturday nights! Enjoy exciting rides for all ages, including a towering 110-foot Ferris wheel, delicious fair food favorites, and incredible shows included free with admission. Experience the dazzling Aqua Live Spectacular featuring aerialist mermaids, The Magic of America illusion show celebrating inspiring moments from American history, and the adrenaline-pumping acts of Victoria Circus with high-wire, aerial, and motorcycle stunts. It’s the perfect event for families and friends to celebrate the start of fair season together!
3. 18th Annual Family Festival
When: Sunday, May 10th
Where: Southampton Elks Lodge #1574, 605 County Road 39, Southampton, NY
Get ready for fun for the whole family at this beloved community carnival at Southampton Elks Lodge #1574! The festival will feature delicious food, exciting games, and thrilling rides for all ages, from high-speed favorites like the Super Slide, Zipper, and Tornado to bumper cars and kiddie attractions. More than just a weekend of entertainment, the event also supports important local initiatives, including children’s health programs, veterans’ assistance, and other community causes led by the Elks.
4. Mamma Mia! Sing-a-Long
When: Saturday, May 9th at 8 PM
Where: The Suffolk, 118 E MAIN ST, Riverhead, NY
Get ready for a night of music, laughter, and nonstop fun at the ultimate feel-good movie event! Join fellow fans for a high-energy sing-along screening of Mamma Mia!, where the lyrics light up the screen and everyone is encouraged to sing, dance, and shout along to all your favorite ABBA hits. With unforgettable songs, disco vibes, and an electric atmosphere, this interactive movie night is the perfect outing for friends, families, and anyone ready to have a fabulous time.
5. Mama Bear Run 5K
When: Saturday, May 9th at 8:30 AM
Where: The Bridges Academy, 339 Snedecor Avenue, West Islip, NY
Lace up your sneakers and join the Mama Bear Run on May 9, 2026, in beautiful West Islip for a fun-filled morning of fitness and community spirit! The Fun Run kicks off at 8:30 AM, followed by the 5K start at 9:00 AM, rain or shine. Participants will enjoy a scenic course through the charming residential streets of West Islip and alongside the picturesque Keith Canal. Be sure to register by April 19th to guarantee your event shirt and get ready for an energizing day for runners of all ages
6. Mother’s Day at Old Westbury Gardens
When: Sunday, May 10th at 10 AM
Where: Old Westbury Gardens, 71 Old Westbury Road, Old Westbury, NY
Celebrate Mother’s Day surrounded by the breathtaking beauty of Old Westbury Gardens. Spend the day strolling through vibrant spring blooms, enjoying the fresh air, and taking in the timeless elegance of the estate dressed in full seasonal color. Relax on the expansive lawns, explore the picturesque gardens, and create special memories with loved ones in a peaceful spring setting designed for slowing down and savoring time together. As a special touch, complimentary lavender plants will be offered to women ages 18 and older while supplies last—providing a fragrant keepsake to bring a little piece of the Gardens home.
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