December is a magical time to explore all that Fairfield County and its surroundings have to offer. From festive holiday events to outdoor adventures, there’s something for everyone to enjoy this season. Whether you're seeking family-friendly activities, romantic escapes, or a way to relax and recharge, this guide has you covered.
Active Adventures
Hit the Ice
Sharpen your skates and embrace the season at the Winter Garden Ice Arena in Ridgefield or the Mill River Rink in Stamford. Perfect for a family outing or an afternoon of fun with friends.
Winter Walks
Take a brisk winter walk through the stunning landscapes of Devil's Den Preserve in Weston or Collis P. Huntington State Park in Redding. These serene trails are perfect for enjoying the crisp air and scenic views.
Axe Throwing Fun
Release some holiday stress with a unique adventure at Blue Ox Axe Throwing in Bridgeport. Perfect for a group activity or a fun date night.
Arts & Culture
Holiday Performances
Enjoy seasonal classics with performances of The Nutcracker at the Palace Theatre in Stamford or A Christmas Carol at the Westport Country Playhouse. These timeless tales are sure to ignite the holiday spirit.
Explore Museums
Immerse yourself in contemporary art at The Aldrich Museum in Ridgefield or delve into local history at the Fairfield Museum & History Center.
Wreath Festivals
Celebrate the season with the beauty of handcrafted wreaths at Newtown’s Wreath Festival or the Pequot Library Wreath Showcase in Southport.
Shopping for the Holidays
Shop Local
Stroll through downtown New Canaan or Westport’s Main Street to discover unique boutiques and festive seasonal decor.
Designer Deals
Find the perfect gifts at Sono Collection or Danbury Fair Mall. For more seasonal finds, check out the holiday shops at Stamford Town Center or the Greenwich Avenue Holiday Stroll.
Mill River Park Lights
Take a stroll under the dazzling lights at Mill River Park in Stamford, and enjoy a pint at their festive Beer Garden.
Relax and Recharge
Holiday Zen
Unwind with a visit to the Salt Cave of Darien or indulge in a relaxing massage at Delamar Southport.
Small-Town Strolls
Wander the twinkling streets of Southport Village, Ridgefield, or Westport, filled with charming shops and festive cheer.
Food & Drink Adventures
Fireside Dining
Cozy up with fireside dining at Grey Barns Tavern in Silvermine or The Schoolhouse at Cannondale in Wilton.
Holiday Bar Crawls
Sip festive cocktails at the Stamford Ugly Sweater Bar Crawl, Fairfield’s Santa Con, or pop into holiday-themed bars in South Norwalk.
Family Fun
Holiday Trees & Santa Photos
Pick your perfect tree at Fairview Tree Farm or Jones Family Farms in Shelton. Capture magical moments with Santa at the Greenwich Reindeer Festival or aboard the Santa Express Train in Danbury.
Holiday Lights
Marvel at glowing decorations at the Holiday Wonderland at Jennings Beach in Fairfield or the Holiday Light Spectacular in Bridgeport.
Brunch with Santa
Enjoy festive mornings with Brunch with Santa events at Lyman Orchards Apple Barrel or the Greenwich Historical Society.
Train Shows
Experience the magic of model trains at the Holiday Express Train Show at the Fairfield Museum & History Center or the Great Trains Holiday Show at the Wilton Historical Society.
Romantic Escapes
Cozy Getaways
Plan a romantic weekend at The Inn at Longshore in Westport or the Roger Sherman Inn in New Canaan.
Scenic Spots
Capture stunning winter photos at Sherwood Island State Park, or enjoy a candlelit dinner at Terra Ristorante in Greenwich.
Beyond Fairfield County
NYC Holiday Highlights
- Visit the world-famous Rockefeller Center Tree and go ice skating under the sparkling lights.
- Catch the Radio City Christmas Spectacular featuring the iconic Rockettes.
- Marvel at the magical holiday window displays at Manhattan’s top department stores, including Saks Fifth Avenue and Macy’s Herald Square.
