North Stamford Christmas Events & Things to Do 2025

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 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...

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...

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.

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...

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.

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 festive spirit at the SM&NC Holiday Market, where over 100 artisans showcase their unique, handcrafted goods. Discover one-of-a-kind gifts, ornaments, and artisanal products in a charming setting. Enjoy seasonal treats and beverages while exploring the historic Bendel Mansion and the beautiful grounds of the Stamford Museum & Nature...

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 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 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...

Step into a charming indoor winter village at the 5th Annual New Rochelle Holiday Market. Discover unique gifts and artisanal products from local makers and businesses, all while soaking in the festive holiday spirit. This event offers a delightful shopping experience in the heart of downtown New Rochelle.

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...

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...

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...

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...

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...

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...

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...

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 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 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.

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...

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.

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 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.

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...