The Weekender December 2 – 3

1. Holiday Illuminations

When: Every Friday, Saturday and Sunday through December 24
Where: Smithtown Historical Society, 239 E Main St, Smithtown, NY

Step into a world of enchantment at Holiday Illuminations, hosted on the picturesque grounds of the Smithtown Historical Society. Immerse yourself in the magic of the season as the historic setting transforms into a winter wonderland of twinkling lights, festive cheer, and heartwarming moments. Join us for an evening filled with delight, featuring dazzling light shows, live performances by local singers, savory delights from food trucks, and unique finds from local vendors. Cozy up by fire pits, where you can reserve a private space to share s’mores with your loved ones. And don’t miss the chance to capture the joy of the season with a visit to Santa beside our towering 55-foot Christmas tree.

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2. Every Christmas Story Ever Told (And Then Some!)

When: Nov 30, 2023 through Dec 23, 2023 (daily)
Where: Smithtown Performing Arts Center, 2 East Main Street, Smithtown, NY

Join us for a one-of-a-kind theatrical extravaganza as three talented actors take a daring detour from the traditional Charles Dickens’ holiday tale. Say goodbye to the usual humbug and embark on an unforgettable journey through the entire spectrum of festive stories, Christmas traditions from around the world, and seasonal icons spanning from ancient times to today’s pop culture.


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3. 7th Annual Holiday Tree Lighting with Santa at The Shoppes

When: Saturday, December 2nd at 4 PM
Where: The Shoppes at East Wind, 5768 Route 25A, Wading River, NY

7th Annual Tree Lighting! Join us on Saturday, December 2 for our annual holiday tree lighting!  Stop by to put a letter in Santa’s mailbox*, enjoy our live DJ entertainment with Sound Entertainment and dance number by all Star Dance Academy, Ride Rudolph on the Carousel, and more holiday fun including holiday shopping.  Santa arrives on a Wading River Fire Department Fire Truck at 6 pm to light the tree.  Bring a new unwrapped toy to support Toys for Tots and the US Marines and bring your camera to take a free photo with Santa.  Admission is free.
Rain Date Sunday, December 3.

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4. Holiday Festival

When: Sunday, December 3rd at 12 PM
Where: Stony Brook Village Center, 111 Main Street, Stony Brook, NY

Celebrate the joy of the season at The Ward Melville Heritage Organization’s 44th Annual Holiday Festival, making a dazzling return on December 3rd, 2023, from 12 PM to 6 PM. Immerse yourself in the festive spirit with a myriad of enchanting activities, including the highlight of the day – Photos with Santa at 2 PM. Witness the charm of a Puppet Procession, be serenaded by delightful Holiday Carolers, and enjoy captivating Live Performances throughout the day. Bring the whole family to experience the wonders of a Petting Zoo and indulge in the timeless joy of Holiday Trains at Wiggs Opticians. The climax of the festivities will be the eagerly anticipated Annual Tree Lighting Ceremony, commencing at 5 PM. Don’t miss out on this magical event filled with cherished traditions, festive cheer, and so much more! Join us for an unforgettable day of holiday magic and community spirit.

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5. 2023 Festival of Trees

When: Dec 01, 2023 through Jan 02, 2024 (daily)
Where: Port Jefferson Village Center, 101 East Broadway, Port Jefferson, NY

Celebrate the holiday season in style as the Port Jefferson Village Center transforms into a festive wonderland adorned with beautifully decorated trees by local businesses, groups, and non-profits. From December 1st to January 2nd, 2024, immerse yourself in the enchanting display of creativity and community spirit. This delightful event is proudly presented by The Greater Port Jefferson Chamber of Commerce, showcasing the collaborative efforts that make our village truly special. The holiday magic is made possible through the generous sponsorship of The Incorporated Village of Port Jefferson, ensuring a season of joy, unity, and celebration for all who visit. Don’t miss the chance to experience the magic of the season at the heart of our community!

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6. St. James – Smithtown Craft Fair

When: Dec 02, 2023 through Dec 03, 2023 (daily)
Where: Smithtown High School East, 10 School Street. St. James, NY

Celebrate the 11th Annual Artisanal Extravaganza, where creativity takes center stage and innovation knows no bounds! This year, our event promises to be bigger and better than ever, with a staggering 85 exhibitors converging to transform the gym into a bustling hub of artistic wonders. Immerse yourself in a world of predominantly handcrafted treasures, adorned with the skillful touch of passionate artisans. From exquisite artisanal, vintage, and new jewelry that sparkles with timeless charm to decorative wreaths that breathe life into any space, this event is a haven for those seeking unique and thoughtful gifts. Indulge your senses with the sweet allure of homemade candies and pamper yourself with organic soaps that redefine self-care. As the festive season approaches, revel in the enchanting array of Christmas décor that will add a touch of magic to your home.

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