Bridgeport Christmas Events & Things to Do 2025

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...

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...

Get into the holiday spirit at the Norwalk Garden Club's annual Christmas Fair. Discover a delightful array of handmade crafts, including unique wreaths, plants, and seasonal arrangements. Browse themed raffle baskets brimming with local gift certificates and treasures. Enjoy complimentary tea, coffee, and hot chocolate at their cafe, and take...

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...

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...

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...

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 Wallingford Holiday Stroll on December 5th! Local merchants along Center Street and surrounding areas will offer special discounts to kickstart your Christmas shopping. Enjoy festive treats, warm drinks, and a chance to meet Santa. Don't miss the cozy bonfire, a dazzling Christmas tree, and exciting...

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.

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 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 holidays with the Norwalk Symphony Orchestra's 'Holiday Pops' concert. This festive celebration features beloved seasonal classics, from Tchaikovsky's 'Nutcracker' to Handel's 'Messiah,' alongside popular tunes like 'Sleigh Ride.' The performance includes captivating choruses, dancers, exciting vocal soloists, and a special surprise guest, culminating in a...

Experience the magic of "Miracle on 34th Street" as a captivating musical at the historic Shubert Theatre. This heartwarming holiday classic, featuring a book and score by Meredith Willson, brings to life the story of Doris Walker and her encounter with the possibility of the real Kris Kringle. Perfect for...

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...

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 enchantment of NUTCRACKER! Magical Christmas Ballet, a holiday tradition for over three decades. This spectacular performance features an international cast of world-class dancers, breathtaking sets, and opulent costumes. Witness the magic of Tchaikovsky's timeless score come alive with whimsical puppetry and dazzling choreography. It's a perfect family outing...

Prepare to be enchanted as the Glow Wild Lantern Festival returns to Connecticut's Beardsley Zoo. This spectacular event transforms the zoo into a breathtaking nighttime wonderland, featuring over 35 larger-than-life, hand-crafted lantern displays. Celebrate wildlife and nature through these illuminated works of art, creating a magical experience perfect for all...

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...

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...

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 enchantment at Lumina, an illuminated forest experience at Harvest Moon Farm & Orchard. Wander through pathways adorned with over half a million brilliant lights, creating a magical glow perfect for all ages. Enjoy captivating light shows synchronized to music, discover new photo opportunities, and savor...

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...

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 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 City of New Haven for a meaningful Hanukkah celebration with an official menorah lighting ceremony on the New Haven Green. This event is a key part of the city's diverse holiday programming, offering a moment of reflection and community spirit.

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.

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...

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...

Join the New Fairfield community for their annual Holiday Lights Parade, a cherished tradition that illuminates the town with festive cheer. Witness a dazzling procession of creatively decorated floats and vehicles, all aglow with vibrant holiday lights, bringing the magic of the season to life.