Last updated: November 11, 2024
Discover the best holiday events in Trumbull with our detailed guide. Whether you're rediscovering your city or visiting for the first time, our guide highlights the best of Trumbull's holidays.
One of the most magical experiences during this festive season is the 16th Annual Greenwich Reindeer Festival & Santa's Workshop, where families can meet Santa and his reindeer, creating lasting memories. Another delightful highlight is Santa's Wonderland at Bass Pro, where visitors can enjoy stunning holiday displays and unique shopping experiences. And the Night of Lights Merry Christmas Hayride is something you definitely don't want to miss, offering a cozy ride through beautifully illuminated displays. See more details on these and other fun events and activities below!
Contact information and details below.
Holiday hayride with Santa and festive decorations.
Embark on a festive holiday hayride through Fairview Tree Farm's beautifully decorated and lit tree fields and holiday scenes. Visit with Santa, Mrs. Claus, and other festive characters while enjoying the holiday spirit and cozy bonfires.
Where: Shelton | More Info: Night of Lights Merry Christmas Hayride
Elaborate and colorful Christmas light display.
A spectacular Christmas light display in Fairfield, Connecticut, featuring elaborate and colorful decorations that attract thousands of visitors each year.
Where: Fairfield | More Info: Wonderland at Roseville
Unique holiday light display in a charming town setting.
The Trumbull Light Tour features a spectacular display of holiday lights and decorations throughout the town, showcasing the community's festive spirit.
Where: Trumbull | More Info: Trumbull Light Tour
Community celebration with Santa, car parade, and holiday treats.
Light Up Monroe is a community event at Travelers Park in Monroe, WA, featuring Santa and Mrs. Claus, a Car Parade, Cocoa and Cookies, and Christmas Carols.
Where: Monroe | More Info: Light up Monroe
Spectacular walk-through light display with thousands of lights.
Sterling Road in Trumbull transforms into a dazzling display of over 15,000 lights, creating a vibrant and joyful atmosphere for all to enjoy.
Where: Trumbull | More Info: Sterling Road / Santa's Runway
Unique blend of historical items and family-friendly activities.
The Monroe Historical Society's Christmas Fair features a sale of membership forms, books, and other Monroe items, along with farm coloring pages and illusion activities for kids. Information about the society's properties, including the One Room Schoolhouse and Meeting House, will be available.
Where: Monroe | More Info: Christmas Fair - Monroe Historical Society
Extended hours for a more extensive holiday tree display.
The Festival of Trees is a spectacular display of beautifully decorated trees, offering a delightful holiday experience with extended hours this year.
Where: Newtown | More Info: Festival of Trees, a Newtown Holiday Festival Event
Local artisans and community performances.
Join Celebrate Shelton for the 10th Annual Community Tree Lighting & Holiday Market at Veterans Memorial Park in Downtown Shelton. Enjoy hot cocoa and cookies while shopping local artisans, visiting Santa and Mrs. Claus, and watching performances by local school choirs and community bonfires.
Where: Shelton | More Info: Community Tree Lighting & Holiday Market
Unique shopping experience with local artisans and holiday treats.
The 9th annual Holiday Pop-Up Market at the Fairfield Museum and History Center features a variety of local vendors selling gifts, home decor, and unique items. Enjoy a festive atmosphere with Santa's appearance on Saturday and delicious snacks from Keifer’s Kettlekorn on Sunday.
Where: Fairfield | More Info: Popshop Holiday Market
Local artisans selling handmade gifts and seasonal items.
Ansonia's Holiday Marketplace is a vendor market featuring local artisans and craftspeople selling handmade gifts, seasonal items, and unique holiday treats. The event takes place at the Ansonia Armory Building on December 2, 2023, from 11:00 AM to 5:00 PM.
Where: Ansonia | More Info: Ansonia's Holiday Marketplace
Santa visit with model trains and festive backdrop.
Meet Santa and his elf at the Holiday Express Train Show at the Fairfield Museum. Families are welcome to take their own photos with Santa in front of a special display. This event is free with museum admission.
Where: Fairfield | More Info: Santa Visits the Holiday Express Train Show
Classic tale of redemption with Broadway-style music.
Trumbull Community Theatre presents "A Christmas Carol, The Musical," a timeless tale of redemption and hope, featuring Ebenezer Scrooge's transformative journey through his past, present, and future.
Where: Trumbull | More Info: A Christmas Carol - Trumbull Community Theatre
Traditional winter ballet performance with elaborate sets and costumes.
Rockwell Dance Center presents a captivating performance of The Nutcracker, showcasing the technical foundation and artistic expression of its dancers in a traditional winter ballet.
Where: Bridgeport | More Info: Rockwell Dance Center's A Winter Ballet - Nutcracker
World-class ballet performance with elaborate sets and costumes.
The Newtown Centre of Classical Ballet & Voice presents The Nutcracker Suite, a classic ballet performance featuring elegant choreography and beautiful costumes. This event is part of the annual Holiday Festival, offering a delightful experience with access to other festive activities.
Where: Newtown | More Info: Newtown Centre of Classical Ballet & Voice - The Nutcracker Suite
Immersive theatrical experience with a limited audience size.
A new adaptation of Charles Dickens' classic, this immersive theatrical experience follows Ebenezer Scrooge through the grounds of St. Paul's Episcopal Church, featuring a choir, dancing, and a festive party. The audience will be guided through various rooms, including Marley's Counting House and Bob Cratchit's home, with carolers, figgy pudding, and apple cider.
Where: Fairfield | More Info: A Christmas Carol Experience
Live reindeer meet-and-greet with Santa.
The 16th Annual Greenwich Reindeer Festival & Santa's Workshop is a cherished town tradition where visitors can have their photo taken with Santa, meet live reindeer, and enjoy activities like the Reindeer Coloring Station and Letter Writing to Santa Station. This event supports Kids in Crisis and offers a fun family experience just minutes from downtown Greenwich.
Where: Greenwich | More Info: 16th Annual Greenwich Reindeer Festival & Santa's Workshop
Free photos with Santa and festive holiday activities.
Santa's Wonderland at Bass Pro Shops offers a free family Christmas event with free photos with Santa, holiday giveaways, games, and gifts. Families can enjoy a festive video featuring their photo with Santa and participate in various holiday activities.
Where: Bridgeport | More Info: Santa's Wonderland at Bass Pro
Holiday celebration with beloved zoo characters.
Join Frosty the Snowman and his friends for a continental breakfast at the Beardsley Zoo's Carousel Building. Enjoy visits with Frosty, Stripes the Tiger, and Thirsty the Penguin, along with carousel rides and family fun.
Where: Bridgeport | More Info: Breakfast with Frosty at the Zoo
Family-friendly holiday breakfast with school choirs and food trucks.
Join us for a festive Holiday Breakfast at FLHS Cafeteria, featuring a delightful morning with school choirs, food trucks, and a beer garden.
Where: Fairfield | More Info: Holiday Breakfast
Interactive Christmas celebration with Santa.
Join us for a delightful Breakfast with Santa at Stratford Park Hotel, where children can enjoy a full English breakfast, hot beverages, pancake and waffle buffet, and Christmas crafts. Santa will personally take their letters and present them with a special gift.
Where: Stratford | More Info: Breakfast with Santa
Meet Santa in a historic dairy barn setting.
Santa Visits Jones Family Farm offers a delightful holiday experience where children can meet Santa amidst the picturesque farm setting, surrounded by the beauty of nature and the charm of the historic dairy barn.
Where: Shelton | More Info: Santa Visits Jones Family Farm
Largest decorated Christmas tree in the area with an 85-foot tall eight-pointed star.
The Bethlehem Christmas Town Festival is an old-fashioned Christmas celebration surrounding the Town Green, featuring over 70 craft vendors, photos with Santa, a hayride, free scavenger hunt, and a 5K road race. The event includes a classic vehicle decorating contest, illuminated fire truck procession, and a beautifully decorated 85-foot Christmas tree.
Where: Bethlehem | More Info: Bethlehem Christmas Town Festival
Holiday fair with diverse vendors and activities.
The Holly Fair at St. Margaret Mary Church in Shelton features a variety of activities including craft vendors, a bake sale, basket raffle, white elephant, and health screenings, all set amidst a holiday atmosphere with Santa in attendance.
Where: Shelton | More Info: Holly Fair
