Smithtown Christmas Events & Things to Do 2025

Discover the 12th Annual St. James - Smithtown Craft Fair, where over 100 exhibitors fill Smithtown High School East with an impressive array of handcrafted goods. This popular event showcases exquisite jewelry, decorative wreaths, homemade candies, organic soaps, and a wide variety of Christmas decor. It's the perfect place to...

Discover the 32nd Annual Northport Winter Craft Fair, Long Island's premier 2-day indoor craft event. This highly anticipated fair showcases a beautiful selection of artists, crafters, bakers, photographers, and more. Enjoy live music performances and festive refreshments while browsing unique, handmade treasures. Admission is free, making it a perfect holiday...

Step into the enchanting Willy Nilly Christmas Store, an extension of the beloved Willy Nilly Trading Company in Bay Shore, Long Island. This festive destination offers a magical array of holiday merchandise, perfect for finding unique gifts and seasonal decor. Discover an eclectic mix of personal and home accessories, from...

Discover unique handmade treasures and festive holiday gifts at the Ascension Church Deer Park Annual Holiday Craft Fair. This event brings together local artisans showcasing a variety of crafts, decorations, and seasonal items. It's the perfect opportunity to find one-of-a-kind presents and get into the holiday spirit.

Experience the magic of the 5th Annual Holiday Stroll in Westport, CT, co-sponsored with Dan Woog's '06880'. This festive event on December 6, 2025, transforms downtown Westport into a winter wonderland. Discover unique finds at the Holiday Winter Market, enjoy children's activities like face painting and Santa photos, and be...

Kick off the holiday season at the New Canaan Nature Center's annual Holiday Market. Discover a delightful array of unique gifts, including handcrafted jewelry, artisanal candles, and stylish clothing from over a dozen participating vendors. Enjoy the festive sounds of live holiday music performed by School of Rock, creating a...

Experience the magic of the 23rd Annual Downtown Lamplight Stroll, a cherished holiday tradition in Milford. Hundreds of families gather to explore participating businesses, collecting stamps in their stroll passports while enjoying sweet treats and warm beverages. Discover unique gifts from over 60 vendors on the green, be serenaded by...

Experience the magic of the 17th Annual Greenwich Reindeer Festival & Santa's Workshop. This beloved tradition brings Santa and his live reindeer to Sam Bridge Nursery & Greenhouses for festive family photos and holiday cheer. Enjoy activities like letter writing to Santa, reindeer coloring, and exciting raffles, all while supporting...

Experience the magic of 'A Christmas Carol' as a vibrant musical at the John W. Engeman Theater. This production brings Ebenezer Scrooge's transformative journey to life, complete with visits from Marley and the ghosts of Christmas Past, Present, and Future. Featuring music by Alan Menken and lyrics by Lynn Ahrens,...

Experience the magic of Charles Dickens' A Christmas Carol as a spectacular musical adaptation. Follow the journey of the miserly Ebenezer Scrooge as he's visited by three ghosts who guide him through his past, present, and future. With music by Alan Menken and Lynn Ahrens, this heartwarming tale is the...

Immerse yourself in a breathtaking musical journey that explores the divine light and human fear surrounding Christ's birth. This powerful Christmas celebration, "BEHOLD…The Moment!", intertwines the sacred beauty of the Nativity with the harsh realities of King Herod's tyranny. Experience soul-stirring music and angelic proclamations that offer a profound meditation...

Experience the magic of the season with the Massapequa Philharmonic Orchestra's Holiday Celebration. This festive event features a delightful program of classical masterpieces and beloved holiday tunes, including Tchaikovsky's 'Waltz of the Flowers' and Anderson's 'Sleigh Ride.' A special vocal performance will bring popular holiday songs to life, and the...

Immerse yourself in the festive spirit with the Massapequa Philharmonic's 'Sounds of the Season.' This annual holiday symphonic extravaganza features the acclaimed Broadway vocalist Sarah Ellis, promising an unforgettable performance of exhilarating holiday music and beloved seasonal favorites. Join the audience for an inspiring sing-along and experience a newly commissioned...

Experience the magic of the season with 'Holiday in The Warehouse,' a heartwarming cabaret show featuring acclaimed singers Maureen Hamill, Mary Richard, and Kerry Lambert, accompanied by music director David Harris. They will present a delightful program of Broadway favorites, timeless standards, and festive cheer, reminiscent of classic holiday films....

The Fairfield University Glee Club presents its annual Christmas concert, 'A Feast of Carols.' This year's program celebrates American Christmas music, featuring beloved tunes from historical hymns to modern classics. The concert includes a festive brass ensemble and invites the audience to join in singing traditional carols.

The Westport Country Playhouse presents 'A Sherlock Carol,' a critically acclaimed holiday tradition. This inventive theatrical production merges the beloved characters of Charles Dickens and Sir Arthur Conan Doyle, following a grown-up Tiny Tim as he enlists Sherlock Holmes to solve the mystery of Ebenezer Scrooge's death. Expect a delightful...

Prepare for a dazzling spectacle at the GSSC's Holiday Light Show, a magical walk-through experience at Camp Edey. Wander along a festive trail adorned with enchanting light displays, many uniquely crafted by Girl Scouts. Capture cherished memories at photo spots, including a grand Christmas tree, and enjoy the 'Chill Zone'...

Step into a magical holiday experience at Waterdrinker's Winter Wonderland, opening November 2025 in Manorville. They feature thousands of twinkling lights, a charming Airstream Christmas Village, and a festive Christmas Tree Farm. Enjoy s'mores by the fire, ice skating, and enchanting photo opportunities with Santa and the Grinch.

Embark on a magical journey through the enchanting Christmas experiences at Bayville Winter Wonderland! Explore the top Christmas attractions on Long Island, where the spirit of the season takes a thrilling and festive twist. Unwrap the wonders of the Best Christmas Wonderland on Long Island, NY, as you immerse yourself...

All aboard for a magical journey to the North Pole on The Holiday Wish Express! This beloved tradition returns to Stamford Town Center, transforming over 20,000 square feet into the region's largest indoor holiday wonderland. Families can enjoy a virtual train ride, meet Santa's toymakers, visit Mrs. Claus's kitchen, and...

Step back in time to the glamorous 1920s at Planting Fields for an enchanting evening. The Main House will be artfully decorated for the season, creating a magical atmosphere. Guests can enjoy festive cocktails and exquisite hors d'oeuvres while celebrating the holiday spirit and supporting the Planting Fields Foundation.

Experience the magic of the holiday season at the Annual Tree Lighting and Holiday Parade. This cherished community event marks the official start of festive celebrations, featuring a heartwarming tree lighting ceremony and a lively parade. Gather with friends and family to usher in the holiday spirit.

Get into the holiday spirit with the Town of Islip's annual Holiday Parade and Christmas Tree Lighting. This beloved event brings the community together for a festive celebration, kicking off the holiday season with cheer and merriment.

Step into a festive wonderland at the Port Jefferson Lantern Light House Tour. This enchanting evening event invites visitors to stroll through the charming streets of Port Jefferson, illuminated by the warm glow of lanterns. Experience the magic as historic homes are beautifully decorated, offering a unique glimpse into the...

Get into the holiday spirit with the annual Port Jefferson Santa Parade and Visit. This beloved community event features a festive parade bringing Santa Claus to town, followed by an opportunity for children to meet him. It's a magical way to celebrate the start of the holiday season and create...

Join the Constantino Brumidi Lodge for a delightful Breakfast with Santa. This family-friendly event offers a delicious breakfast spread, fun crafts, and exciting raffles. Bring your camera to capture precious moments with Santa, making it a perfect holiday outing for all ages.

The Port Jefferson Festival of Trees transforms the village center into a festive holiday wonderland. This event invites the community to participate by sponsoring beautifully decorated trees, with options available for different tiers. It's a delightful way to embrace the holiday season and support local initiatives.

Experience the magic of the holidays at the Patchogue River Christmas Parade. This beloved annual tradition transforms the river into a dazzling spectacle of illuminated boats. Thousands gather to witness this festive kickoff to the holiday season, making it a perfect, free family outing.

Experience the magic of the season at the Center Moriches FD Holiday Parade of Lights. This festive event features a dazzling procession of fire departments, ambulance companies, and community groups, all showcasing their vehicles decorated with vibrant holiday lights. The parade culminates with a special appearance by Santa Claus, arriving...

Capture the magic of the holiday season with a visit to Santa at Ridge Hill. This popular event allows families to create lasting memories with professional photos alongside Santa Claus. While specific dates for 2025 are yet to be announced, the event typically runs throughout the holiday season, offering a...

Experience the charm of Milford's annual Christmas Parade, a cherished tradition held the Saturday after Thanksgiving. This festive event brings the community together with colorful floats, lively music, and the much-anticipated arrival of Santa Claus. It's a perfect way to kick off the holiday season with hometown cheer.