Concierge Calendar - December 2025

Happy Holidays! Fairfield County is bustling with activity this December, closing out the year in style. We've curated a list of events and ideas to enlighten, entertain, and inspire, ensuring you and your loved ones make the most of this holiday season.

Click on any image below for more details on activities that we hope will help you enjoy each and every wonderful day!

12/1 Cyber Monday? Still at your computer looking for bargains? We say just grab these streaming deals and take a lunch hour stroll to visit a local retailer. Their personal attention is sure to beat AI's gift-giving suggestions! Then get ready to give back, with inspiration from GivingTuesday. 12/2 Building a Future An affordable one. Did you know in Fairfield County 27% of renters spend more than 50% of their income on housing costs? Fairfield Community Foundation sponsors tonight's open house, film and panel discussion surrounding this important topic.

12/3 Brain Games Are you ready to sharpen your mind and enjoy a strategic challenge? Join the adult chess club at the Westport Library. Seasoned players and curious beginners welcome! Wednesdays from 6:30 - 9:00pm. 12/4 Homemade Gelt Enjoy some crispy latkes and a splash of vodka while crafting delicious gelt for the upcoming Hanukkah festival. BE Chocolat is hosting this fun night out for adults (7 - 8:30pm)

12/5 Silent Night Enjoy music of the season performed by Music on the Hill's Festival Chorus with harp & strings. Familiar carols will be sung by the audience during this peaceful evening at the UU Congregation in Westport. 12/6 Main Street USA A relatively new (5 years old) but charming tradition, brings the community together in Westport. Stroll through the special offerings of retailers and restaurants while enjoying music and seasonal festivities (4 - 7pm).

12/7 Heights & Lights Tree lighting with a twist - a rappelling Santa and fireworks! Stamford makes a night of it, starting with a 22-story decent at Landmark Square and ending at Latham Park with holiday music. 12/8 Movie Monday A reimagined classic short film, in 4D! Feel the wind on your face, smell the cookies and trees as Rudolph and his new friends work together to save Christmas. Daily at Maritime Aquarium.

12/9 Field Trips Verso University launches its newest series — a traveling cooking club! This class meets at Westport's Choupette Crêperie where participants will learn the secrets behind making delicious, sweet and savory crêpes. 12/10 Handcrafted ❤️ Afterschool, send your youngster (grades 3 -5) to Lachat Town Farm to make holiday gifts for special people in their lives. Handmade and beautifully wrapped, the gifts will be a highlight of the holiday season.

12/11 Festive Couture The exchange project comes to Westport, in collaboration with Cove Collective. Join our associate, Lisa Holler at this evening event. Great finds. great prices, great energy and great for the environment too! 12/12 Clever Creations The Pottery Factory in Norwalk is full of fun. Walk-in to paint your own pottery, take a class to master the wheel, or enjoy other events like soap and candle making. Tonight, turn sea glass and shells into seasonal art!

12/13 Finding Family Fill gaps in your family genealogy with the help of experienced genealogists. Explore Pequot Library’s genealogy collection, including family and military histories, plus other books that cannot be found online. 12/14 Mansion Holiday The Lockwood Matthews Mansion is all decked out! At today's open house (12 - 4pm) you'll see Santa and his loyal elf plus a special performance by the East Coast Contemporary Ballet.

12/15 Celebration Gather at Pequot Library for a Menorah lighting, music by DJ Marv, latkes and donuts. Part of the Chanukah celebration sponsored by Chabad of Westport, Chabad of Fairfield and the Pequot Library. 12/16 Carillon Concert Catch a performance tonight by Fairfield Warde's orchestra, band and choir in a seasonal spectacular. Fairfield Ludlow's Candlelight Concert is on the 19th. Both schools offer two performances at 6:30 and 8:30pm

12/17 Okay to Delay An evening of insightful conversation on how advances in AI are transforming humanity and redefining connections. Thoughts on how this will impact the next generation and why parents should know it is ok to delay their child's use of smart phones and social media. 12/18 A Sherlock Carol Two literary legends collide when a grown-up Tiny Tim calls on Sherlock Holmes to investigate the mysterious death of Ebenezer Scrooge. This witty mystery will delight audiences of all ages at Westport's Country Playhouse. Nightly, through December 21st.

12/19 Wonderful Life As his happy life begins to unravel on Christmas Eve, George Bailey is given an amazing opportunity — to view the world as if he'd never been born. Catch this classic tonight at Sacred heart's Community Theatre. 12/20 Bells & Whistles Wilton Historical Society hosts two festive sing-alongs today, in conjunction with Music on the Hill. Make a jingle bell craft and be sure to save time to check out the Great Trains holiday display.

12/21 Santa's Circus Prepare to be mesmerized by global artists' remarkable acrobatics that blend theater, dance, and gymnastics. Stunts, skills, magic and illusions will make for a joyful and enchanted evening at the Palace in Stamford. 12/22 Sugar & Booze Best known for her unforgettable characters and spot-on impressions during her six seasons on Saturday Night Live, Ana Gasteyer brings her playful and soulful vocal chops to the Westport Country Playhouse.

12/23 Support Group The holidays can be a difficult time for those that have suffered the loss of a spouse. Don't go it alone. Join the free, ongoing, bereavement support group, facilitated by Waveny LifeCare network. Mondays, Tuesdays in Wilton. 12/24 Flying tonight Last chance to see the reindeer at the 17th Annual Greenwich Reindeer Festival and Santa's Workshop! Take a photo with Santa, create a holiday craft and name a baby reindeer. Last minute shopping? Greenwich Ave is close!

12/25 Christmas Day May you have a wonderful and blessed holiday surrounded by family and friends. We love that the warmth of home is at the heart of every Christmas celebration. For those that don't celebrate this holiday, a beach walk will be invigorating! 12/26 Lake Compounce It's the final year for Holiday Lights and we are down to the last three days! Mingle among half a million lights and enjoy some family fun rides, special events and holiday treats. Ride the North Pole Express and visit CT's largest Christmas Tree.

12/27 Outdoor Skate The Longshore rink is open! It's the perfect day to lace up those skates and get some fresh air/exercise. Warm up afterwards with hot chocolate and enjoy the setting along Long Island Sound. 12/28 CBGBs in CT Celebrate the birthplace of Punk and New Wave at FTC with an electrifying night of live music. Not an average tribute show—this will feature several major super guests including Chris Frantz and Tina Weymouth!

12/29 Climbing Camp Rock Climb Fairfield will keep the kids busy and challenged during the winter break. New to climbing or ready to take their skills to a new level, this week-long, half-day or full-day camp will be fun and exhilarating. 12/30 For 100 Years! Jaw dropping moves, "no way" shots, gravity defying dunks — it's the Harlem Globe Trotters 100 year tour. They are on tonight at Bridgeport's Total Mortgage Arena. Entertaining for the whole family - don't miss it!

12/31 New Year's Eve Some go for the glitz and glamour. Others stay home and enjoy a quieter evening. For an in-between option of casual fun head to 314 Beer Garden in Norwalk. Live music by the high energy, modern rock band BadBoy, will keep things lively. Champagne toast at midnight — no cover, no reservations.

Newcomer or long-timer, we hope you all find something new to enjoy near home this month. Reach out to chat!

KMS Team at Compass 203.295.4375 kmsteam@compass.com kmscompass.com

Compass Connecticut, LLC is a licensed real estate broker. All material is intended for informational purposes only and is compiled from sources deemed reliable but is subject to errors, omissions, changes in price, condition, sale, or withdrawal without notice. No statement is made as to the accuracy of any description or measurements (including square footage). This is not intended to solicit property already listed. No financial or legal advice provided. Equal Housing Opportunity. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions.

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