Seasonal & Holidays
2025 Monroe Holiday Guide: Lights, Festive Fun & Good Cheer
From small-town charm to seasonal celebrations, these hometown holiday highlights bring the spirit of the season to life.
The holiday season has arrived in Monroe, bringing twinkling lights, cheerful events and plenty of ways to make memories close to home. From light displays to beloved local traditions, here are the hometown holiday highlights you won’t want to miss.
Please note: Dates and details are subject to change, so be sure to check with each organizer before you go — many events require tickets or reservations in advance.
Victorian Christmas at Monroe Congregational Church
When: Saturday, Dec. 6, 2025| 10 AM–3 PM
Where: Monroe Congregational Church, 34 Church St, Monroe, CT
Find out what's happening in Monroefor free with the latest updates from Patch.
The Victorian Christmas Fair brings the charm of the 19th century to life with festive sights, handmade gifts, hearty seasonal treats and costumed docents sharing local history. Guests can browse artisan-made treasures, enjoy soups and hand pies, sip period-style mocktails and explore a beautifully decorated Meetinghouse on guided tours. Families will love the Victorian train display, children’s craft room and a visit from Father Christmas, who will be collecting new, unwrapped toys for Covenant to Care.
More info: See Facebook event
Find out what's happening in Monroefor free with the latest updates from Patch.
Monroe Historical Society Christmas Fair
When: Saturday, Dec. 6, 2025 | 10 AM–4 PM
Where: Monroe Historical Society, 433 Barn Hill Rd, Monroe, CT
Discover a festive mix of Christmas and holiday décor, including both new and vintage ornaments perfect for any style. Browse beautifully crafted wreaths, delicious baked goods and unique Monroe historical collectibles. With even more seasonal treasures to explore, it’s a great place to find gifts and decorations. Don’t forget to bring your reusable bags for easy shopping!
More info: monroecthistory.org
Stepney Green Holiday Tree Lighting
When: Saturday, Dec. 6, 2025 | 7–8 PM
Where: Stepney Green, Main St. & Pepper St, Monroe, CT
Join the Save Our Stepney Task Force as a new 12-foot Norway spruce is lit for the first time, surrounded by glowing luminaries and giant LED snowflakes. Expect music from local singers, donuts from Boy Scout Troop 62, hot chocolate and cookies, a visit from Frosty the Snowman on a fire truck and commemorative ornaments while supplies last. Non-perishable food and monetary donations for the Stepney Baptist food pantry are welcome.
More info: See Facebook event
“Mr. Gruber’s Silent Night” One-Act Play
When: Sunday, Dec. 7, 2025 | 10 AM (during worship)
Where: Monroe Congregational Church, 34 Church St, Monroe, CT
This original one-act play shares the inspiring story behind the beloved Christmas carol “Silent Night,” bringing its history to life during a special worship service at Monroe Congregational Church. Attendees are invited to contribute unwrapped toys for children and teens supported by DCF, helping spread holiday joy to local families. The church warmly welcomes everyone to join in this meaningful blend of storytelling, community giving and seasonal spirit.
More info: themonroesun.com
Holiday Sing-Along with Joy Blooms
When: Monday, Dec. 15, 2025 | 9 AM
Where: Edith Wheeler Memorial Library, 733 Monroe Turnpike, Monroe, CT
Get ready for a festive, family-friendly holiday concert with Joy!, featuring an upbeat blend of original songs and classic seasonal favorites. This interactive show invites guests of all ages to sing along, celebrate and soak in the magic of the season. With plenty of energy, holiday cheer and New Year spirit, it’s the perfect way to keep the bells ringing and hearts glowing. No registration is required to attend.
More info: patch.com/connecticut/monroe
40th Annual Holiday Festival – Newtown Youth & Family Services
When: Sunday, Dec. 7, 2025 | 11 AM–4 PM
Where: Main St, Newtown, CT
Experience the 40th Annual Holiday Festival, a long-standing Newtown favorite filled with festive activities for all ages. Explore the Holiday Market, tour decorated homes, enjoy The Nutcracker Suite and take in the dazzling Festival of Trees. Kids can join in holiday stories, cookie workshops, gingerbread fun and more, while adults enjoy trolley rides and an online silent auction — all benefiting NYFS programs.
More info: newtownyouthandfamilyservices.org/Special-Events/holiday-festival
Trumbull Holiday Tree Lighting
When: Friday, Dec. 5, 2025 | 5 PM
Where: Trumbull Town Hall Gazebo, 5866 Main St, Trumbull, CT
Join us for the annual Holiday Tree Lighting, featuring festive entertainment led by MC Tyler Cohen and music from the Madison Middle School Band. Guests can enjoy a winter photo booth, hot chocolate, candy canes and treats from Maefair Healthcare Center and Little Kernel's Kettle Corn. The Long Hill Fire Department will be on-site to help kick off the celebration, and a community holiday sing-along will add to the cheerful atmosphere. Be sure to stick around for a special visit from Santa to close out the night!
More info: trumbull-ct.gov/1079/Holiday-Tree-Lighting
Trumbull Historical Society Holiday House Tour
When: Saturday, Dec. 6, 2025 | 11 AM–4 PM
Where: Trumbull Historical Society, 1856 Huntington Turnpike, Trumbull, CT (tour check-in)
Enjoy a self-guided tour of five uniquely decorated homes and a historic church, each dressed up for the holidays. The Trumbull Historical Society’s annual tour blends architecture, local history and festive décor, making it a lovely way to spend a December afternoon just a short drive from Monroe. This event requires tickets to attend.
More info: trumbullhistory.org
Enjoy the season, make a few memories close to home and have a happy holiday, Monroe!
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