Things to do this weekend in and around Fairfield County

Friendly fun in Fairfield County for Friday, December 5, 2025 through Sunday, December 7, 2025. Check out these highlights!

(Scroll down for full list of weekend activities.)

Lumina: A Magical Light Experience at Harvest Moon Farm & Orchard - December 4-6, 2025 - North Salem, NY. Experience a dazzling winter wonderland with over half a million glowing lights and new holiday scenes at this walk-through light event.
After School Childcare Programs at the YMCA of Greenwich - Ongoing - Greenwich, CT. Year-round after-school programs designed to build confidence, resilience, and friendships for youth development.
Expressive Twos at Katonah Art Center - December 5, 2025 - Mt Kisco, NY. Art classes for toddlers aged 22-36 months focusing on process-oriented creative expression.
STEM Career Showcase at Connecticut Science Center - December 5, 2025 - Hartford, CT. A showcase event highlighting STEM careers with activities and exhibits for kids and families.
Holiday Stroll: North Pole at Lounsbury House - December 5, 2025 - Ridgefield, CT. Evening holiday stroll featuring festive decorations and activities from 6 pm to 9 pm.

17th Annual Greenwich Reindeer Festival & Santa’s Workshop - November 28 to December 24, 2025 - Greenwich, CT. Meet Santa and his live reindeer, enjoy Santa’s Workshop, and take festive photos at this beloved town tradition.
Little Red Bar[n] Live Music at Bishop's Orchards - December 6, 2025 - Guilford, CT. Enjoy live local music in an open-air setting welcoming all ages from 6:30 pm to 9:30 pm.
Free mini photo session with Shoott! - Connecticut - December 6, 2025 - New York, NY. Celebrate family moments with a free 30-minute outdoor photo session; pay only for photos you love.
Curtain Call's Fall 2025 Dramatic Arts Classes - December 6, 2025 - Various locations. Acting, improv, musical theatre, and more classes for kids, teens, and adults with flexible scheduling.
Santa Express at Railroad Museum of New England - Naugatuck Railroad - December 6, 2025 - Thomaston, CT. Early afternoon train rides with Santa scheduled at 12 pm and 2:15 pm for a festive family experience.

Sleepover, An Original Musical by TADA! Youth Theater - December 7, 2025 - New York, NY. Enjoy a family-friendly musical with performances at 2 pm and 4:30 pm.
Essex Steam Train: 2025 North Pole Express - December 7, 2025 - Essex, CT. Holiday-themed train rides with multiple departure times; check website for details.
Expressive Twos at Katonah Art Center - December 6, 2025 (also on Dec 7) - Mt Kisco, NY. Creative art sessions for toddlers focusing on intuitive and process-oriented art.
Next Stop: SANTA! At The Shore Line Trolley Museum - December 7, 2025 - East Haven, CT. Meet Santa and enjoy trolley rides from 11 am to 4 pm in a festive setting.

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