From sparkling ice rinks and festive train shows to cozy igloos and classic holiday traditions, discover the best seasonal activities across Fairfield County and beyond.
Fairfield County, Connecticut transforms into a winter wonderland each holiday season, offering magical experiences for kids, families, couples, and anyone looking to celebrate. From outdoor ice skating rinks and festive holiday lights to cozy indoor events, unique dining experiences, and day-trip destinations, here’s your SEO-optimized guide to the best things to do this winter.
Whether you're planning family outings, weekend adventures, or memorable holiday celebrations, these activities will surely put you in the spirit of the season.
❄️ Outdoor Winter Fun in Fairfield County
Outdoor Ice Skating Rinks
Experience classic winter fun at these popular outdoor skating spots:
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WPAL Rink at Longshore – Westport
https://www.westportct.gov/government/departments-a-z/parks-recreation/longshore-ice-rink -
Mill River Park Cohen Skating Rink – Stamford
https://millriverpark.org/portfolio/cohen-skating-center/ -
Boucher Community Ice Rink – New Canaan
https://l i n k . n e w c a n a a n c t . g o v -
Gorham’s Pond – Darien (weather-permitting)
https://www.darienct.gov -
Redding Community Center – Redding
https://www.townofreddingct.org -
Gould Manor Park – Fairfield
https://www.fairfieldct.org
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Owen Fish Park – Fairfield
https://www.fairfieldct.org -
Whalen Pond – Brookfield
https://www.brookfieldct.gov -
Kent Pond – Wilton
https://www.wiltonct.org
🎄 Holiday Events & Family Activities
Celebrate the season with festive events across Lower Fairfield County:
Worldwide Lights Celebration – Stepping Stones Museum, Norwalk
https://www.steppingstonesmuseum.org
Selfies with Santa – The SoNo Collection, Norwalk
https://www.thesonocollection.com
Breakfast with Frosty – Beardsley Zoo, Bridgeport
https://www.beardsleyzoo.org
Festival of Lights – Hope River Farm, Fairfield
https://www.hoperiverfarm.com
🚂 Holiday Train Shows in Connecticut
Train lovers and families will adore these magical holiday displays:
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Holiday Express Train Show – Fairfield Museum & History Center (Dec 7–29)
https://www.fairfieldhistory.org/events/holiday-express-2024/ -
Great Trains Holiday Show – Wilton Historical Society
https://wiltonhistorical.org/holiday-train-show/ -
Holiday Wish Express – Stamford
https://www.stamfordtowncenter.com/events -
Holiday Train Show – Essex Steam Train & Riverboat
https://essexsteamtrain.com/events/holiday-train-show/
⛸️ Indoor Ice Skating Rinks in Fairfield County
Perfect for cold or snowy days, these indoor rinks offer public skate, lessons, and family fun:
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Nutmeg Curling Club – Bridgeport
https://nutmegcurling.com -
Wonderland of Ice – Bridgeport
https://wonderlandofice.com -
Danbury Arena – Danbury
https://danburyice.com -
Darien Ice Rink – Darien
https://www.darienicerink.com -
Dorothy Hamill Skating Rink – Greenwich
https://www.greenwichct.gov -
Greenwich Skating Club – Greenwich
https://www.greenwichskatingclub.org -
Milford Ice Pavilion – Milford
https://milfordice.com -
New Canaan Winter Club – New Canaan
https://ncwinterclub.com -
SoNo Ice House – Norwalk
https://sonoice.com -
Winter Garden Ice Arena – Ridgefield
https://wintergardenarena.com -
Sports Center of Connecticut – Shelton
https://sportscenterct.com/ice-rinks/ -
Stamford Twin Rinks – Stamford
https://stamfordtwinrinks.com -
Terry Conners Rink – Stamford
https://www.terryconnersrink.com