Ossining Christmas Events & Things to Do 2025

Step back in time to experience Charles Dickens' beloved tale, 'A Christmas Carol,' as performed by Michael Muldoon, embodying Dickens himself. This captivating one-hour show, set within the beautifully decorated art gallery of Lyndhurst Mansion, brings Ebenezer Scrooge and his iconic journey to life. It's a chance to witness a...

Awaken your holiday spirit with a joyous concert by Collective Brass at the historic Lyndhurst Mansion. They will perform seasonal favorites, including selections from The Nutcracker, new arrangements of ancient carols, and a rousing rendition of the Hallelujah Chorus. This festive event is perfect for the whole family and promises...

Prepare for a genuine New York holiday tradition with Jessica Lynn's "A Very Merry Classic Christmas." This acclaimed show, celebrated as a top holiday event, offers a dazzling multi-media spectacle featuring dancers, marching bands, and choirs. Sing along to beloved Christmas carols and become part of an immersive experience that...

For 30 years, Rob Mathes has kicked off the holiday season with a spectacular concert. This high-energy event features Mathes, his all-star band, and a chorus, delivering a unique blend of rock, jazz, and blues with fresh takes on holiday classics and original compositions. It's a cherished local tradition that...

The Westchester Ballet Company presents a spectacular 75th-anniversary production of The Nutcracker. Directed and choreographed by Sabrina Gail Lobner, this full-length ballet features exquisite scenes, stunning costumes, and exciting special effects. Performed at the Lehman Center for the Performing Arts, it's a beloved holiday tradition for audiences of all ages.

Celebrate the holiday season with the 15th Annual Christmas in New York concert. This special event features the talents of TaRanda Greene, Charles Billingsley, RamCorps, and the American Festival Choir. Immerse yourself in the festive spirit with a night of uplifting holiday music.

The Radio City Christmas Spectacular, starring the legendary Rockettes, returns to celebrate its 100th anniversary. This iconic holiday show promises an unforgettable experience with dazzling choreography, festive music, and breathtaking stagecraft. Witness the precision and magic of the Rockettes as they bring classic Christmas tales and holiday cheer to life...

Prepare for an unforgettable evening as the celebrated Italian tenor Andrea Bocelli graces the stage at the iconic Madison Square Garden. His return promises a night filled with breathtaking performances and timeless melodies that have captivated audiences worldwide.

Get ready for a swinging, rocking holiday celebration with the Rock This Town Orchestra's Christmas Spectacular! This family-friendly show brings the most wonderful time of the year to life with energetic performances of beloved Christmas classics. Expect a full stage production filled with festive cheer, and a special surprise appearance...

Experience the magic of Westchester's Winter Wonderland, a spectacular drive-thru holiday light extravaganza. Journey through 1.2 miles of dazzling lights from your car, enhanced by the free Otocast app that plays festive music and stories. It's an affordable and memorable way for the whole family to celebrate the holiday season...

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 into a world of enchantment at 'Let It Glow,' a spectacular holiday lantern event. This immersive experience transforms familiar spaces into a dazzling wonderland, showcasing thousands of illuminated lanterns. Prepare to be captivated by intricate designs and vibrant displays that bring the magic of the season to life.

Step into a world of miniature marvels at the Holiday Train Show, NYC's beloved winter tradition. Model trains chug past nearly 200 iconic landmarks, each intricately crafted from natural plant materials. Discover new surprises for the 2025/2026 season, including a replica of the Delacorte Theater, set within the warm Enid...

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...

Immerse yourself in the enchanting holiday spirit of New York City by exploring its world-renowned Christmas window displays. From the avant-garde designs of Bergdorf Goodman to the festive storytelling at Macy's and the dazzling light show at Saks Fifth Avenue, these displays transform the city into a winter wonderland. Don't...

Join the CityCenter Danbury for their 3rd Annual 'Light the Lights-Winter Festival' on the Green. This free, family-friendly event features the illumination of a 40-foot holiday tree, Santa's arrival by fire truck, a festive fire truck parade, holiday shopping from various vendors, live entertainment, and free cookies and hot chocolate....

The Rockefeller Center Christmas Tree Lighting Ceremony is a quintessential New York holiday tradition. Witness the spectacular illumination of the 75-foot Norway Spruce, adorned with over 50,000 LED lights and a dazzling Swarovski star. The tree, arriving from East Greenbush, New York, will be a beacon of festive cheer throughout...

Discover the charm of Westchester's holiday season with a curated collection of artisan markets and boutiques. Forget generic gifts and find truly unique treasures from local artists and craftspeople. Explore handcrafted ceramics, jewelry, fiber art, and more, all while supporting the vibrant creative community. Many events feature special activities, festive...

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...

Discover unique, handcrafted treasures at the annual Holiday Pottery Show & Sale. This anticipated event features over 30 regional ceramic artists, jewelers, and artisans offering a convenient way to shop locally for the holidays. Members can enjoy an exclusive preview and a special discount, while proceeds benefit the artists and...

Experience a vibrant holiday celebration at NYSoM HolidayMania 2024! This free event offers a festive journey through multiple winter holidays, featuring a special gift giveaway, engaging activities in Hanukkah Town and Kwanzaa Village, and a Winter Wonderland with beloved characters. It's a perfect way to spread holiday cheer for all...

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...

Experience the magic of the Columbus Circle Holiday Market, a cherished New York City tradition. This vibrant market brings together over 100 artisans and designers, offering a dazzling array of unique gifts, from handmade jewelry and art to home goods. Indulge in a global culinary journey with festive food options...

Experience the quintessential New York City holiday season at The Plaza Hotel, where Central Park meets Fifth Avenue. Indulge in festive dining, including special holiday teas and private dining options. Shop for unique gifts at The Plaza Boutique or online, and immerse yourself in the hotel's spectacular seasonal decorations. Don't...

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.

Kick off the holiday season at the Hudson River Museum with a festive weekend packed with activities for all ages. Immerse yourself in Victorian splendor with guided tours of the beautifully decorated Glenview historic home. Enjoy captivating planetarium shows, engaging family art and science workshops, and enchanting storytelling sessions.

Spark creativity this holiday season at the Hudson River Museum's Family Science Workshop. Participants will craft unique holiday ornaments inspired by stellar nebulae, the cosmic nurseries where stars are born. Design your own illuminated model of these celestial wonders or let your imagination soar to new galaxies.

Join the festive 'Downtown for the Holidays' celebration in Ridgewood, NJ, featuring a special visit from Santa Claus and his elves. They will travel along Ridgewood Avenue in a Santa Cart, stopping for greetings, before heading to the tree lighting ceremony. Children can explore emergency vehicles during the 'Trucks on...

Ridgewood Guild's Winterfest is a beloved annual event offering a magical holiday experience for the entire family. Attendees can enjoy live music, captivating ice sculptures, and heartwarming storytelling. Festive treats like hot chocolate, cookies, and candy canes are provided, and Santa Claus himself will be present for photos. Special activities...

Step into Bergen County's Winter Wonderland for a magical holiday experience. Glide across the ice on the main rink or enjoy exhilarating rides on Blitzen's Bumper Cars. Families can capture cherished memories with a visit to Santa, and a carousel ride is included with select tickets. Indulge in festive treats...

Experience the iconic New Year's Eve celebration in Times Square, the symbolic center of New York City. Witness the legendary Ball Drop, add your wishes to the confetti, and enjoy live entertainment. This global tradition unites millions in a joyous farewell to the past year and a hopeful embrace of...