1. Donald Harrison's Quantum Leap Music Festival
When: Aug 14, 2025 through Aug 17, 2025 (daily)
Where: Borghese Vineyard, 17150 Middle Road (Route 48), Cutchogue, NY
2022 NEA Jazz Master Donald Harrison joins forces with local production group NOLA 2 NOFO to present an unforgettable Quantum Leap Music Festival 2025. Featuring a curated line-up of more than two dozen Grammy-winning artists, from legendary New Orleans icons to rising stars from New York, the festival promises an extraordinary fusion of music, culture, and flavor. Guests will enjoy farm-to-table food and expertly paired wines at Long Island, NY’s oldest winery, creating a one-of-a-kind experience where world-class performances meet exceptional culinary artistry.
2. The Atelier presents a Summer of Creativity and Fun
When: Aug 14, 2025 through Aug 16, 2025 (daily)
Where: The Atelier at Flowerfield, 2 Flowerfield, Suite 6 & 9, St. James, NY
The Atelier presents A Summer of Creativity and Fun, offering an exciting lineup of one-day workshops to inspire and delight. Whether you’re a beginner or an experienced artist, there’s something for everyone—from learning how to stretch and prime your own canvas to exploring color theory, figure drawing, or illuminating your portrait. Dive into the vibrant world of oil, watercolor, gouache, or acrylic painting, or get creative by painting and decorating your denim jeans or jacket. With so many engaging options, you’re sure to find the perfect workshop to spark your imagination this summer.
3. TriviaFest
When: August 16th - 23rd
Where: Schnitzels, 77 Main Street, Stony Brook, NY
TriviaFest ‘25 kicks off this weekend! Gather your team and join the fun by playing on either Saturday or Sunday at 3 PM. The top four teams from each day will advance to the finals for a chance to claim ultimate bragging rights. Spots are limited, so DM or call Schnitzels to reserve your team’s place in the tournament. Come see (or be) the smartest minds on Long Island in action!
4. Long Island Oyster Jamboree
When: Saturday, August 16th at 1 PM
Where: Smith Point County Beach, 1 William Floyd Pkwy, Shirley, NY
On August 16th, head to Smith Point Beach for a day of coastal flavor and community spirit. Enjoy freshly harvested Long Island oysters alongside outstanding food, perfectly paired beer and wine, and the relaxing seaside atmosphere. Meet local oyster farmers and fisheries who produce some of the nation’s finest shellfish—both a culinary delicacy and an ecological asset that filters our waters, supports marine habitats, and fuels our coastal economy. Savor the taste of our local waters, connect with the chefs and farmers behind each bite, and discover the sustainability efforts keeping Long Island’s oyster heritage thriving for generations.
5. S-Mile Swim Challenge
When: Saturday, August 16th at 8 AM
Where: Foster Memorial Beach, 1000 Noyack-Long Beach Rd, Sag Harbor, NY
The S-Mile Swim Challenge invites participants to dive into the open water with their choice of swimming 1 mile, 0.5 mile, or 0.25 mile. Every swimmer will receive a commemorative S-Mile Swim Challenge shirt and swim cap. For those seeking to compete or track their performance, Elitefeats will provide professional timing, with medals and prizes awarded to winners in each distance. Participants may also choose to swim at their own leisurely pace without being timed, making this event perfect for both seasoned swimmers and those just looking for a fun experience. Safety is a top priority, with SVOR lifeguards on duty to ensure a secure and enjoyable swim for all.
6. 30th Annual Ellen's 5K Run/Walk/Virtual
When: Sunday, August 17th at 9 AM
Where: Southampton Intermediate School, 70 Leland Lane, Southampton, NY
Ellen’s Run, now in its 30th year, is The Ellen Hermanson Foundation’s signature 5K (3.1-mile) fundraising event dedicated to raising awareness about breast cancer. Held annually on the East End of Long Island—an area with some of the highest breast cancer diagnosis and mortality rates in New York—the event unites the community in support of breast health education, screenings, and patient care. Since its first race, which drew over 500 participants and raised $62,000, Ellen’s Run has grown to nearly 1,000 participants and has become the largest race on the South Fork. Over the past 29 years, The Ellen Hermanson Foundation has awarded more than $6 million in grants, making a profound impact in the fight against breast cancer.