Cheshire Christmas Events & Things to Do 2025

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...

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...

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...

Discover unique handmade treasures and festive holiday spirit at St. Michael's Christmas Artisan Bazaar. This charming event, held indoors at the Church Hall, offers a delightful array of crafts and Christmas-themed items from local artisans. It's the perfect opportunity to find one-of-a-kind gifts and soak in the holiday atmosphere.

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!

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...

Discover unique, handcrafted treasures at the Guilford Art Center's Holiday Expo 2025. This highly anticipated event showcases the work of talented Connecticut and New England artists, offering a diverse selection of ceramics, jewelry, textiles, woodworking, and more. Shoppers will find the perfect holiday-themed gifts, from festive ornaments to artisanal home...

Immerse yourself in the festive spirit of Barcelona this Christmas with a dazzling array of free family activities. Witness the city come alive with spectacular light displays, explore historic Christmas markets like Fira de Santa Llúcia, and participate in beloved Catalan traditions such as finding the 'Tió de Nadal'. From...

Experience the magic of the season at the 38th Annual West Hartford Holiday Stroll. This beloved New England-style event transforms West Hartford Center and Blue Back Square into a festive winter wonderland. Guests can meet Santa, enjoy live music from multiple stages, and savor culinary delights from local eateries. Victorian...

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...

Join the Oliver Wolcott Library for their annual Festival of Trees, a magical evening to kick off the holiday season. This highly anticipated event features a full open bar, lavish hors d'oeuvres, and a stunning display of decorated trees and wreaths. It's the perfect community celebration to get into the...

Experience the festive spirit at the Torrington Christmas Holiday Festival & Flea Market. This vibrant event brings together a wide array of vendors offering unique crafts, holiday decorations, and artisanal goods. It's the perfect opportunity to find special gifts and enjoy a day of community celebration.

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 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 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 Glow Hartford, a spectacular light festival and market. Wander through illuminated gardens and marvel at giant, themed displays. Join Santa's Sleigh Adventure to help save Christmas, enjoy live entertainment, and find unique gifts at the festive market. It's an unforgettable winter wonderland...

All aboard the 2025 North Pole Express for a magical nighttime train journey to the North Pole! Celebrate the season with Santa and Mrs. Claus, enjoy festive sing-alongs, and indulge in hot chocolate and sugar cookies. Each child receives a special gift from Santa, and pajamas are encouraged for a...

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....

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.

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...

Immerse yourself in the holiday spirit with Connecticut Ballet's enchanting production of The Nutcracker. This annual tradition features dazzling performances by principal dancers from New York City Ballet and American Ballet Theatre, accompanied by the live Hartford Symphony Orchestra. Following each show, guests have the unique opportunity to meet and...

Hartford Stage presents its cherished holiday tradition, 'A Christmas Carol: A Ghost Story of Christmas.' Follow Ebenezer Scrooge on a profound journey of redemption as he confronts his past, present, and future with the help of three spirits. This mesmerizing production promises a magical theatrical experience, bringing the timeless story...

The Nutmeg Ballet's production of The Nutcracker is a cherished Connecticut holiday tradition. Directed by Victoria Mazzarelli, this iconic ballet brings Tchaikovsky's masterpiece to life, enchanting audiences of all ages with its magical storytelling, stunning choreography, and festive atmosphere. It's a perfect way to immerse yourself in the holiday spirit.

Young men are invited to immerse themselves in a profound 3-day silent retreat, designed to foster spiritual growth and prepare for Christmas. Following the methodology of the Spiritual Exercises of St. Ignatius Loyola, participants will engage in deep reflection and prayer amidst beautiful, scenic surroundings. This experience offers expert guidance...

Get ready for the Naugatuck Holiday Bash, a festive celebration designed to bring the community together for a joyous holiday season. This event promises a delightful experience for all, with activities and attractions that capture the spirit of the holidays. It's the perfect opportunity to create lasting memories with family...

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.

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.

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.