Darien Christmas Events & Things to Do 2025

Step into a festive winter wonderland with Irving Berlin's White Christmas, a heartwarming musical at Curtain Call Inc. Follow two charming veterans on a romantic quest to a Vermont lodge, filled with song, dance, and holiday cheer. This uplifting production features a dazzling score with beloved classics, promising a delightful...

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...

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....

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 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.

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...

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.

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...

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...

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...

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...

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...

Step into a winter wonderland at the Holidays on the Hill Train Show, featuring an all-new, immersive G-scale train display across 2,500 square feet. Explore whimsical settings and nostalgic scenes within the stunning Lasdon Glass House Conservatory. Meet Santa Claus in his cozy cottage and embark on a fun scavenger...

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....

All aboard The Snow Clipper for The First Gift Express! This popular, personalized gift-giving experience with Santa and Mrs. Claus has sold out for the past three years. Enjoy a festive train ride, explore museum exhibits, and receive the first gifts of Christmas. Evening departures offer a magical view of...

Experience the enchantment of the season at Fairview Tree Farm's 'Night of Lights' Merry Christmas Hayride. This beloved annual event offers a magical 30-minute tractor-pulled journey through dazzling light displays and festive holiday scenes. Meet beloved characters like Santa, Mrs. Claus, and the Grinch, and enjoy the warm glow of...

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...

Discover unique, handcrafted gifts for loved ones at the Holiday Market. This event showcases exceptional items by local artists and crafters, offering a chance to support area talent while finding distinctive treasures that will be cherished. It's the perfect place to find special goodies for others, and perhaps a treat...

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 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 a festive holiday craft festival in Shelton, Connecticut, featuring a curated selection of artisanal goods. Browse unique handmade items perfect for Christmas gifts and enjoy a day of festive shopping. This event is a prime opportunity to find one-of-a-kind treasures from talented local creators.

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...

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...

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.

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...

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 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.

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.

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.