1. Setauket Country Craft Fair
When: Saturday, September 13th at 10 AM
Where: Setauket Village Green, 5 Caroline Ave, Setauket, NY
The Setauket Country Craft Fair is a vibrant community event featuring over 60 local craft and gift vendors offering unique, handmade treasures. Guests can enjoy live music throughout the day, delicious food, and a special plant sale, making it the perfect outing for families, friends, and anyone who loves to shop local and support artisans.
2. 11th Annual Port Jefferson Dragon Boat Race Festival
When: Saturday, September 13th at 8:30 AM
Where: Harborfront Park, 101 East Broadway, Port Jefferson, NY
Join us for the 11th Annual Port Jefferson Dragon Boat Race Festival on Saturday, September 13, 2025, from 8:30 AM to 5:00 PM at Harborfront Park, 101 East Broadway, Port Jefferson, NY. Spend the day enjoying exciting boat races, live entertainment, local vendors, and delicious food trucks. This year, we’re adding a fun twist with our brand-new Dog Dragon Costume Contest—a must-see for pet lovers! Bring your family and friends for a full day of culture, community, and celebration by the harbor.
3. The 22nd Annual Hicksville Chamber of Commerce Street Fair
When: Sunday, September 14th at 10 AM
Where: Nelson Avenue, 45 Nelson Avenue, Hicksville, NY
The 2025 Hicksville Street Fair is moving to an exciting new location—Nelson Avenue, a vibrant quarter-mile stretch just south of Hicksville Station alongside Newbridge Road. This year’s fair promises the same beloved family fun with even more space to explore! Enjoy our magnificent craft fair, featuring dozens of artisans and vendors with one-of-a-kind creations, from wooden crafts and handmade jewelry to clothing, baked goods, home décor, and more. Savor delicious bites at LI Bites, our premier food truck rally, and let the kids burn off energy at the huge FunZone, packed with giant slides, bouncers, and obstacle courses. Groove to live music and DJ sets from our mobile stage, and don’t miss the sweetest treat—free ice cream for the first 500 kids 12 and under! Admission is free, making it the perfect day out for the whole family.
4. Dog 'Dragon' Costume Contest
When: Saturday, September 13th at 11 AM
Where: Harborfront Park, 101 A East Broadway, Port Jefferson, NY
New to this year’s Annual Port Jefferson Dragon Boat Race Festival is the Dog “Dragon” Costume Contest! Bring your furry friends dressed in their most creative dragon-inspired outfits and join the fun on Saturday, September 13, 2025, at 11:00 AM in Harborfront Park (101-A West Broadway, Port Jefferson, NY 11777). Don’t miss this chance to show off your pup’s style, enjoy the festive atmosphere, and be part of a one-of-a-kind celebration!
5. 2nd Annual KiDS NEED MoRE 5K Run/Walk & 1/4M Kids Fun Run
When: Saturday, September 13th at 8:30 AM
Where: Belmont Lake State Park, Belmont Lake State Park Serene Picnics and Recreation on the Water, West Babylon, NY
At KiDS NEED MoRE, our mission is to create a strong, supportive community that brings joy, builds lasting memories, and inspires hope and resilience in children facing serious illness. By joining us for this 5K, you’re doing more than just running—you’re helping provide life-changing experiences for children with cancer and their families. Your participation supports programs filled with laughter, friendship, and moments of pure joy during incredibly challenging times. Held in September, Childhood Cancer Awareness Month, this event is a powerful way to honor and uplift families while raising awareness and directly supporting our flagship program, Camp Adventure.
6. Second Sunday Castle Tours
When: Sunday, September 14th at 1 PM
Where: Bayside Historical Society, 208 Totten Avenue, Fort Totten, Bayside, NY
Step inside history with the Bayside Historical Society! On the second Sunday of each month, from 1:00 PM to 3:00 PM, staff and volunteers will be offering guided tours of The Castle and its exhibitions. Each tour lasts about 45 minutes, with two sessions available—the first beginning at 1:00 PM and the second at 2:00 PM. Admission is free, but reservations are required. Don’t miss your chance to explore this local treasure—reserve your spot in advance for the September 14th tour.