December is one of the most magical times of the year in Fairfield County. From festive holiday markets and winter strolls to cozy dining, family fun, and cultural events, the area offers endless ways to celebrate the season. Whether you’re planning weekend outings, date nights, or time with family and friends, here are the best things to do across Fairfield County and nearby towns this December.

❄️ Active Winter Adventures

Hit the Ice

Sharpen your skates and enjoy seasonal ice skating at:

• Winter Garden Ice Arena (Ridgefield): https://wintergardenarena.com/

• Mill River Park Rink (Stamford): https://millriverpark.org/ice-rink/

Winter Walks & Nature Trails

Bundle up and explore beautiful winter landscapes at:

• Devil’s Den Preserve (Weston): https://www.ctwoodlands.org/explore/devils-den-preserve

• Collis P. Huntington State Park (Redding): https://portal.ct.gov/DEEP/State-Parks/Parks/Huntington-State-Park

Axe Throwing Fun

Release holiday stress at Blue Ox Axe Throwing (Bridgeport): https://blueoxaxethrowing.com/bridgeport/

🎭 Arts & Culture

Holiday Performances

• The Nutcracker – Palace Theatre (Stamford): https://palacestamford.org/

• A Christmas Carol – Westport Country Playhouse: https://www.westportplayhouse.org/

Museums to Explore

• The Aldrich Contemporary Art Museum (Ridgefield): https://thealdrich.org/

• Fairfield Museum & History Center: https://www.fairfieldhistory.org/

Wreath Festivals

• Newtown Wreath Festival: https://www.newtownct.gov/

• Pequot Library Wreath Showcase (Southport): https://www.pequotlibrary.org/

🛍 Holiday Shopping in Fairfield County

Shop Local

Stroll the charming streets of:

• Downtown New Canaan: https://www.newcanaanchamber.com/

• Westport Main Street: https://www.westportdma.com/

Seasonal Shopping Centers

• SoNo Collection (Norwalk): https://www.thesonocollection.com/

• Danbury Fair Mall: https://www.danburyfairmall.com/

• Stamford Town Center: https://stamfordtowncenter.com/

• Greenwich Avenue Shopping District: https://greenwichchamber.com/

Mill River Park Holiday Lights + Beer Garden

https://millriverpark.org/

🧘 Relax & Recharge

Holiday Zen

• Salt Cave of Darien: https://saltcaveofdarien.com/

• Delamar Southport Spa: https://delamarsouthport.com/spa/

Small-Town Holiday Strolls

Explore the magic of:

• Southport Village

• Ridgefield: https://destinationridgefield.com/

• Downtown Westport

🍽 Food & Drink Adventures

Fireside Dining

• GreyBarns Tavern (Silvermine): https://greybarntavern.com/

• The Schoolhouse at Cannondale (Wilton): https://schoolhouseatcannondale.com/

Holiday Bar Crawls & Festive Cocktails

• Stamford Ugly Sweater Bar Crawl: https://heystamford.com/

• Fairfield SantaCon: https://www.fairfieldsantacon.com/

• South Norwalk Holiday Pop-Ups: https://www.sonowalkable.com/

🎅 Family-Friendly Holiday Fun

Christmas Trees & Santa Photos

• Fairview Tree Farm: https://www.fairviewtreefarm.com/

• Jones Family Farms (Shelton): https://www.jonesfamilyfarms.com/

• Greenwich Reindeer Festival: https://www.greenwichreindeerfestival.com/

• Danbury Railway Museum Santa Express: https://www.danburyrailwaymuseum.org/

Holiday Light Displays

• Jennings Beach Holiday Wonderland (Fairfield): https://fairfieldct.org/

• Holiday Light Spectacular (Bridgeport): https://www.bridgeportct.gov/

Brunch with Santa

• Lyman Orchards Apple Barrel: https://lymanorchards.com/

• Greenwich Historical Society: https://greenwichhistory.org/

Holiday Train Shows

• Fairfield Museum Holiday Express Train Show: https://www.fairfieldhistory.org/events/holiday-express/

• Wilton Historical Society Great Trains Holiday Show: https://wiltonhistorical.org/

💑 Romantic Winter Escapes

Cozy Getaways

• The Inn at Longshore (Westport): https://longshoreinn.com/

• Roger Sherman Inn (New Canaan): https://rogershermaninn.com/

Scenic Spots & Dining

• Sherwood Island State Park: https://portal.ct.gov/DEEP/State-Parks/Parks/Sherwood-Island-State-Park

• Terra Ristorante (Greenwich): https://terraristorante.com/

🎄 NYC Holiday Highlights (A Quick Train Ride Away!)

• Rockefeller Center Tree: https://www.rockefellercenter.com/

• Radio City Christmas Spectacular: https://www.msg.com/radio-city-music-hall

• Famous Window Displays: Saks, Macy’s, Bergdorf Goodman, Bloomingdale’s

•  

Whether you're planning weekend activities, date nights, or family outings, this month is full of local magic — and we’re here to help you enjoy every moment of it.