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A Top Fairfield County Winter Wonderland


As the Christmas season approaches, people are excited about the fun holiday activities coming up. Nowhere is more full of winter and the holiday spirit than Connecticut, and the Fairfield County area turns into a veritable winter wonderland every year. Children get to enjoy the winter excitement, and adults get to relive the joy of youth as they experience the Christmas magic, from shopping to sleigh rides to Connecticut’s Polar Express. For Connecticut natives and visitors in the surrounding area, there are many Fairfield County things to do during the winter months.

Sleigh rides


There is nothing that says winter magic like a carriage pulled over the snow by horses. People enjoy delightful trips through the bright and beautiful snow-covered fields — an experience that is quintessentially Connecticut. No method of travel matches a sleigh ride. Journey over pristine, snow-covered hills with a cup of hot chocolate or cider, snuggled up under a blanket, listening to the cheerful jingle bells. It is the perfect winter activity, whether as a memorable family experience, an adventure with friends, or a romantic date.

Holiday shopping


Every year, Fairfield puts on a Holiday Shop and Stroll event where guests can walk down the street and do their Christmas shopping while enjoying the festive atmosphere. Taking place on Thursday, December 8, 2022, the 10th annual event offers special discounts and other prizes. The participating shops will offer various seasonal refreshments and stay open late while carolers and local school musicians walk the streets, filling the air with holiday songs. The Holiday Shop and Stroll is sponsored by the Fairfield Chamber of Commerce and the Town of Fairfield and is a great opportunity to have a fun night out while supporting local businesses. People can finish their whole shopping list as the stores offer jewelry, fashion items, toys, gift cards, home decor, best-selling books, sporting goods, and much, much more.

The Polar Express

Connecticut boasts a glorious and exciting train ride based on the popular animated Christmas movie. Guests get to ride in the vintage 1891 Rutland train, covered with Christmas lights inside and out, making it glow as it steams down the tracks. Hot chocolate is served for first-class travelers while Santa Claus rides the train to greet every passenger. The elves are also aboard and will lead the travelers in various Christmas carols. Pajamas are recommended, especially for children. The train leaves at a multitude of different times over the weekends, giving guests a variety of times to choose from and fit their availability. Get into the holiday spirit with singing and laughter as the train travels through beautiful Connecticut scenery.

Stamford light show

In Downtown Stamford, there is a dazzling, festive, and larger-than-life experience waiting for anyone who takes the Holiday Stroll through the holiday light displays. The path is open from November through December 24 from 4-9 p.m. Food and drinks will be available for everyone on site from a variety of excellent vendors and food trucks. Both cold and hot beverages will be available, while guests over 21 can visit the Blind Rhino Winter Beer Garden, where they can enjoy special brews, wine, cider, or other seasonal drinks.

For children, there are many carnival rides, such as Dizzy Dragon, a giant slide, Red Baron, and more. In the Holiday Village, Christmas music fills the air while people enjoy the 30-foot tall, interactive Christmas tree with a show of stunning lights and sounds every 30 minutes. The festival also includes gigantic 3D ornaments, a 16-foot-high gingerbread house, candy cane arches, and massive, glittering, spangled stars.

Indoor carousel


The Brownstein Selkowitz Carousel Pavilion is an indoor carousel built specifically for Mill River Park. The carousel boasts 30 handcrafted, unique animals in 12 sections, with two accessible ones. Each animal, from the decorated horses to the more whimsical birds, fish, rabbit, frog, and insects, is a species native to Stamford, Connecticut. During the winter, the carousel is open on weekends from 9 a.m.-5 p.m., and snacks are available at the Carousel Cafe. The pavilion and carousel are also possible to rent for birthdays and other events, as well as hosting Carousel Storytime.

Winter Wonderland

On December 17, New Canaan Nature Center transforms itself into a stunning winter wonderland, putting on a spectacular day of holiday fun. Guests can enjoy the Wacky Winterland scavenger hunt, holiday crafts, reindeer games, and roasting marshmallows. The Red and Green Cafe offers food and hot beverages like coffee and cocoa, and large model trains portray the town of New Canaan. For the first time, the 2022 Winter Wonderland offers train rides for all ages on the Roaming Railroad.

Moving to Fairfield County

For anyone looking into Fairfield County real estate, Lisa Migliardi combines industry expertise with a passion for the process into a stellar experience for her clients. Lisa’s determination and hard work have made her a leader in the residential Connecticut real estate industry. Dedicated, knowledgeable, and passionate about real estate, she advises her customers through every step of the process, whether they are buyers or sellers, leading to a satisfying closing day, which is her favorite aspect of every deal.

Contact Lisa for professional real estate advice today.



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For ten years, Lisa was the controller of a luxury design firm in town. While in this position, she assisted in creating elite custom homes and lifestyles for her clients, which ultimately led her to discover a love and passion for real estate.
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