From strolls and tree lightings to ice skating, theater shows, and day-trip favorites, here are the top holiday events happening across Fairfield County this season.
The holidays are here, and Fairfield County truly shines this time of year. If you’re looking for festive ways to celebrate with family and friends, there’s something magical happening in every town.
Today, I’m sharing seven of my favorite events that capture the charm, tradition, and community spirit that make holidays in Fairfield County so special.
1. Greenwich holiday stroll. This is one of the most iconic events of the season. You’ll find beautifully decorated storefronts, horse-drawn carriage rides, carolers, photos with Santa, and great dining and shopping all throughout downtown. It’s picture-perfect and full of that classic Greenwich holiday magic.
2. Westport holiday stroll and tree lighting. Right in the heart of downtown, experience live music, local vendors, and the tree lighting by the river. Witness the small-town charm, but with that coastal sparkle Westport is known for.
3. Holiday stroll at Mill River Park. Over in Stamford, you can take a full walk-through light experience with huge installations, glowing tunnels, themed zones, and plenty of photo-worthy moments. Kids and adults love it, and it’s one of the most immersive displays in the county.
"From strolls to ice skating to theater shows, our community has no shortage of holiday traditions."
4. Darien Ice Rink holiday skate nights. If you’re looking for a more active option, consider this. Enjoy themed skate nights, festive music, and the timeless charm of a New England rink. The kids are sure to have a fantastic time.
5. Westport Country Playhouse and the Quick Center for the Arts. If you prefer something more artistic, both theaters offer holiday productions every year. You’ll see everything from A Christmas Carol to festive concerts, and sometimes even The Nutcracker. It’s perfect for date night or a family outing if you want a more elevated experience.
6. New Canaan’s holiday stroll and Santa’s workshop. The downtown area turns into a delightful holiday village featuring story time, visits with Santa, and beautifully decorated streets. It truly feels like something out of a movie, capturing the essence of New Canaan.
7. Mystic’s Lantern Light Village and the Essex North Pole Express. Both offer unforgettable New England holiday experiences, especially if you love the whole Polar Express theme.
Fairfield County is full of festive energy this time of year. If you need more recommendations or you’re thinking about making this area home in the near future, feel free to reach out. My contact details are (203) 722-5445 and [email protected]. Let’s connect! I’m always happy to help.
