2025 Upcoming Holiday Events
- Missy
- Nov 17
- 3 min read
Updated: Nov 24
It’s the Most Wonderful Time of the Year and We’ve Got a Full Calendar of Holiday Fun!
Save the dates, because Sayville and Port Jefferson are bringing all the festive magic this season — and your favorite curvy boutiques, Ivory & Main Curvy Bridal and The Curvy Corner Boutique, will be right in the middle of it all!
From Pink Friday and Tree Lightings to Miracle on Main Street, Dickens Festival, and more, there’s no shortage of cozy community events to enjoy.
So grab your friends, bundle up, and make a day of it — shop local, sip something warm, and stop by our boutiques while you’re in town for a little extra sparkle and joy this holiday season.
Here is our full list of upcoming holiday events in our local communities:
Friday, November 21, 2025 | 5-8 pm | Port Jefferson, NY
Stroll through the heart of Port Jefferson Village and discover 24 of your favorite local boutiques, each offering exclusive specials, giveaways, and pink holiday cheer. Shop small and support local businesses this holiday season!
Wednesday, November 26, 2025 | 6-8 pm | Port Jefferson, NY
Join us at the corner of Broadway & East Broadway to watch santa light the Christmas tree and kick off the holiday season! Live music, free hot chocolate, and more!
Saturday, November 29, 2025 | 10 am-9 pm | Sayville, NY
Join us on Main Street in Sayville for the 19th Annual Miracle on Main Street. Start the morning with a holiday parade starting at 10 am. After the parade, Main Street will officially be open for Small Business Saturday, including Santa visits, trolley rides, and more from 11 am - 3 pm. Our tree lighting will take place at 6:30 pm, followed by the Miracle on Main Street main event, including live reindeer, Santa, amusement rides, ice sculptures, train display, Dickens characters, live music & dance performances, movies in the street, old-fashioned games, Gingerbread House Competition, and more!
Saturday, November 29, 2025 | 5:30-6:30 pm | Port Jefferson, NY
See Chandler Square light up for the Holiday Season with this special ceremony! The event will be from 5:30 to 6:30 pm, with the lighting at 6 pm!
Sunday, November 30, 2025 | 3-5:30 pm | Port Jefferson, NY
The Santa Parade starts at Port Jeff railroad and runs down Main Street to the Port Jeff Village Center. Visit with Santa at the village center after the parade!
Saturday & Sunday, December 6 & 7, 2025 | Port Jefferson, NY
The Village of Port Jefferson will magically transform into the Dickensian era with streets filled with roaming characters such as Father Christmas, Dickens Mayor, Scrooge, the Town Crier and the beloved chimney sweeps. The events are open to the public, and most attractions are free of charge. The festivities will feature outdoor ice skating at the Village Center, a cappella performances by choirs and harmony groups, Nutcracker performances, magic shows by The Great Wizard of the North, and more!
Saturday, December 13, 2025 | 5-8 pm | Port Jefferson, NY
Tour multiple decorated homes in Port Jefferson Village and enjoy refreshments and holiday cheer!
Sunday, December 14, 2025 | 5 pm | Sayville, NY
Join us at the Sayville Chamber House for candlelit prayers, music, Hanukkah gelt, potato latkes, and more.
Fridays, November 28, December 5, 12, 19, 2025 | 5-8 pm | Port Jefferson, NY
Experience the magic of the holidays as the Village of Port Jefferson glows with the warm lights of luminaries lining the streets. Enjoys cozy evenings of exploring local shops, boutiques, and restaurants.
Comments