Cheshire Other Christmas Activities 2026

Live Advent with a 3-day silent retreat following the methodology of the Spiritual Exercises of St. Ignatius Loyola. Participants reflect, pray, and receive guidance and mentorship amidst scenic surroundings. The experience is designed to strengthen character and empower young men...

This New England-style holiday tradition fills the streets with live performances across three stages and strolling Victorian carolers. Visitors can meet Santa, watch a community Menorah Lighting, and sample bites from local restaurants. Families can also get an up-close look...

Visitors glide across a 100-by-100-foot outdoor rink located adjacent to the Bushnell Park Pump House. Skaters can bring their own equipment or borrow a pair of skates on site. On weekends, nearby food trucks and hot chocolate from the carousel...

Guests gather in the Trinity College Chapel for an annual holiday service of readings and choral music offered as a moment of comfort and hope. The gathering marks the start of the holiday season for the Greater Hartford community. A...

This festive 3.1-mile road race and walk winds through decorated residential neighborhoods and past holiday shop windows. Participants receive a holiday-inspired beanie and gather for a post-race celebration featuring cookies, hot chocolate, fresh fruit, and grab-and-go snacks. The event also...

Visitors can browse offerings from over 30 local craft vendors, sample items from food trucks, and participate in basket raffles. Family-friendly activities include hayrides, tree decorating, touch a truck, and story time. Children can also take part in games, face...

Gather at the West Haven Green for the community Hanukkah Menorah Lighting Ceremony. The annual holiday event is presented by Mayor Dorinda Borer.

Participants take on a 3.5-mile road race traversing varied terrain throughout the area. The route starts on Hubbard Street and concludes in the parking lot next to the gymnasium. Runners can compete across standard race divisions or take part in...

Tour the beautifully decorated historic Kellogg-Eddy House and Museum during this community open house celebration. Guests can explore the museum exhibits and period rooms while enjoying punch and cookies.

Beginners and future skaters of all ages take to the outdoor rink in Bushnell Park for instructional ice skating. Skaters borrow rental skates ranging from children's size 9 up to adult size 15. Lockers are available in the warming shed...

Participants take on a scenic, rolling-hill 5K course through the heart of the Nichols community, while non-runners can join an untimed 1.25-mile Health Walk. Children can participate in the Jingle Bell Jr. fun run leading to the finish line. The...

Visitors can view a 20- to 30-foot tree constructed from genuine lobster traps, wrapped in white lights, topped with a giant lit star, and covered in hand-painted buoys created by the community. Festivities include the arrival of Santa and Mrs....

Held alongside the Bethlehem Christmastown Festival, this holiday event features a 5K road race, a two-mile walk, and a quarter-mile kids' fun run. Participants start in front of Memorial Hall and can enjoy the festival before and after racing. Awards...

Passengers board a locomotive-powered sleigh for an evening round-trip journey to the North Pole. The holiday experience features festive sing-alongs, hot chocolate, sugar cookies, and visits from Santa and Mrs. Claus. Every child receives a small gift from Santa.

Families can meet Santa, Mrs. Claus, and the Grinch for holiday photo opportunities. Visitors can take a trolley ride with Frosty out to Reindeer land and explore the outdoor petting zoo with grain to feed the animals. An on-site food...

Participants transform retired books into handmade holiday decorations using simple folding and crafting techniques. Attendees can choose to make a Christmas tree, an angel, or a hedgehog. All necessary materials and instruction are provided.

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...

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...

Get ready for the annual Holiday Stroll in Downtown Wallingford on December 4th, 2026! This beloved community event invites everyone to experience the festive spirit as they stroll through the heart of downtown. Discover local businesses and enjoy the holiday...

Step into a magical Christmas Village, a cherished holiday tradition in Torrington. This enchanting event offers a glimpse into the history and festive spirit of the season, inviting visitors to immerse themselves in a world of holiday cheer.

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...

Experience the heartwarming tradition of the Walnut Beach Tree Lighting ceremony. Gather at the Walnut Beach Arch to welcome Santa Claus and witness the magical illumination of the Christmas tree. Enjoy the sounds of carols filling the air and indulge...

Get ready for the return of the Festival de la Infància in Barcelona! This exciting event is packed with games, learning opportunities, and adventures for the whole family. While full details are still to be announced, attendees can anticipate an...

Embark on a magical Santa Express train ride, perfect for families seeking holiday enchantment. Passengers will journey through a winter wonderland, enjoying visits from Santa Claus, Mrs. Claus, elves, and reindeer. Each child receives a special gift from Santa's toy...

Experience Santa's Walking Wonderland, a unique holiday event set on the Indian Rock Nature Preserve's farm. This magical experience offers a personalized visit with Santa and Mrs. Claus, accompanied by their elf entourage. Enjoy festive activities like caroling, crafting, and...

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....

The Mandell JCC invites everyone to celebrate Chanukah, the Festival of Lights, from December 4-12, 2026. Join them for traditional candle lighting ceremonies in the Chase Family Gallery and participate in their annual donation drive, collecting essential items for local...

Discover the rich heritage of Kwanzaa at this community celebration, honoring Pan-African and African American culture. Explore the seven principles, symbols, and colors that define this meaningful observance. Enjoy traditional activities like drumming, storytelling, and a festive Karamu feast, fostering...

Discover the historic Boar's Head Festival, a unique celebration steeped in tradition. This event features a symbolic procession and a blend of music and ceremony, offering a memorable experience for all attendees.

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...

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...

Get ready for the Annual Gingerbread House Festival, a beloved event that transforms the Wood Memorial Library and Museum into a wonderland of edible art. This festival showcases an array of imaginative and meticulously crafted gingerbread houses, offering a delightful...