Shelton Christmas Events & Things to Do 2025

Experience the magic of the season at the 10th Annual Community Tree Lighting and Holiday Market in Shelton, CT. Browse unique gifts from local artisans, enjoy festive music from school choirs, and gather around community bonfires. Santa and Mrs. Claus will be making a special appearance, and children can bring...

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 festive spirit at the Monroe Historical Society's Christmas Fair. Browse a delightful array of Christmas and holiday decor, featuring new and vintage ornaments, charming wreaths, and delicious baked goods. Discover unique Monroe Historical Collectibles, perfect for gifts or personal treasures. Remember to bring your reusable bags for 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 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...

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...

Discover a festive holiday tradition at the Franciscan Christmas Fair, offering a delightful array of handmade crafts, unique gifts, and delicious homemade treats. Browse artisanal goods, decorative greens, and Holy Land carvings, and enjoy a heartwarming Living Crèche presentation. Meet Santa and Mrs. Claus, and support vital community services with...

Gallery 53 transforms into a festive holiday destination for its annual Holiday Artisan Fair. From November 18 to December 23, visitors can explore a curated selection of hundreds of locally handcrafted gifts, perfect for every taste and budget. Enjoy extended hours, including special Thursday evenings with wine and cheese, and...

Experience the magic of the 44th annual Bethlehem Christmas Town Festival, a beloved holiday tradition. Marvel at the towering 85-foot Christmas tree, enjoy live entertainment, and explore over 70 vendors offering unique handcrafted gifts. Don't miss the festive opening ceremony with Santa, the illuminated firetruck procession, and a special 5K...

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 unique holiday treasures at the Wadsworth Mansion Holiday Bazaar. Browse handmade gifts from over 30 artisan vendors, featuring selections from the Open Air Market. Enjoy delicious food and warm beverages from David Alan Catering while you shop for the perfect presents. A festive atmosphere awaits!

Discover unique treasures and festive cheer at the annual Holiday Shopping Fair. This event brings together a curated selection of local artisans and crafters, offering a diverse range of handmade gifts, holiday decorations, and artisanal products. It's the perfect opportunity to find one-of-a-kind presents and immerse yourself in the holiday...

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...

Experience the magic of the holiday season at Fantasy of Lights, a spectacular drive-through light display at Lighthouse Point Park. This cherished annual tradition transforms the park into a winter wonderland with dazzling illuminations and festive music, perfect for all ages. Proceeds from ticket sales support Goodwill of Southern New...

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...

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....

Step into a world of enchantment at the Winter Lantern Festival, Middlefield's must-see illuminated attraction. Wander through a dazzling outdoor display featuring over 1000 handmade Chinese lanterns, creating whimsical scenes and glowing sculptures. This magical experience is perfect for all ages, offering a unique way to light up the season....

Experience the magic of Lake Compounce Holiday Lights for the very last time in 2025. This beloved New England tradition features half a million twinkling lights, Connecticut's tallest 100-foot Christmas tree, and select family rides. Visit Santa, enjoy festive treats, and create lasting memories during this final season.

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...

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 "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...

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....

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...

Get ready for a holiday concert with a playful twist! This event invites attendees to don their most outrageous ugly Christmas sweaters for a festive celebration. Enjoy seasonal classics and toe-tapping tunes performed by the Waterbury Symphony Orchestra, all while embracing the spirit of holiday merriment and mischief.

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...

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 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.

Step back in time with a visit to The Shore Line Trolley Museum, where you can ride historic trolleys along scenic routes. Experience seasonal events, from fall-themed excursions to festive holiday rides. Explore fascinating exhibits showcasing a vast collection of vintage transit vehicles and learn about the rich history of...

Embark on a magical Santa Express train ride, where Santa and Mrs. Claus visit each child, delivering special gifts. Enjoy a festive journey through winter scenery, complete with carols led by elves. This enchanting experience is perfect for families seeking holiday cheer.

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...