Winter in Fairfield County doesn’t mean staying inside — it’s the perfect season to get bundled up, hit the snow and embrace everything frosty and fun
Skating and Sweet Treats
Westport
Westport is a great place to start your winter adventures. Westport PAL Rink at Longshore offers daily public skating, lessons for all ages and the occasional figure skating or hockey clinic.
Gear up nearby: Ski and Sport of Westport and CB Sportiff and has everything you need to enjoy the snow: skis, snowboards, snowshoes, winter jackets, boots and accessories. Stop in to outfit yourself or the whole family.
Tip: Grab a delicious cup of hot chocolate at Retreat Sweets and walk the Westport Ramble, a 1.2-mile loop trail near the downtown area that is easy to complete and offers forest views—super scenic on a snowy morning.
Ski, Snow, and Gear
New Canaan
New Canaan might be small, but it’s big on winter adventure. Ski and Sport in New Canaan carries all the gear you’ll need for snow sports, sledding or exploring winter trails. It offers a full range of winter boots, jackets, gloves and accessories for kids and adults.
Tip: Pack a thermos of hot cocoa and make a day of hitting local sledding hills — the neighborhood slopes here are perfect for kids and families.
Snow-Ready Essentials
Darien
Darien offers a mix of family-friendly sledding hills and nearby ice rinks, perfect for weekend outings. Darien Sport Shop and Orvis Darien are your go-to stores for winter gear—think brands like Canada Goose, waterproof jackets, snow boots, hats, gloves and everything else you need to stay warm while outdoors.
Tip: Winter beach walks at Compo Beach are an excellent way to get some fresh air and enjoy the views.
Hills, Trails, and Ice
Fairfield
Fairfield is packed with sledding spots for all ages. Favorites include Tunxis Hill Park, Gould Manor Park, and local school grounds like Fairfield University at the corner of Round Hill Road and Barlow Road for easy access. Ice skating is available at neighborhood rinks, and for adventurous families, the area’s trails offer snowshoeing and cross-country skiing.
Tip: Believe it or not, some farmers’’markets keep the season going through winter. Swing by the Westport Farmers’ Indoor Market or the Black Rock Farmers’ Market in Bridgeport for fresh, local produce.
Trails and Winter Exploration
Wilton
Wilton’s parks and open fields are perfect for snowshoeing, cross-country skiing or just a fun walk in a winter wonderland. Many local trails like the Mianus Maze Trail or Saugatuck Falls wind through scenic woods, and the town’s small hills make great sledding spots for kids.
Gear up nearby: Sporting stores in Wilton like Outdoor Sports Center carry everything you need for a day outside.
Tip: Try a group snowshoe or cross-country ski adventure if you want to explore beyond the sledding hills.
Cruises and Ice Adventures
Norwalk
Norwalk adds a little extra variety to winter fun. The Maritime Aquarium offers weekend seal-spotting cruises through April, giving families a chance to see Long Island Sound’s marine life in the chilly months. Snowy trails along the Norwalk River Valley Trail are ideal for snowshoeing or cross-country skiing.
Gear up nearby: DICK’S Sporting Goods in Norwalk has a wide selection of winter gear, from sleds and skates to jackets and boots, perfect for preparing for all types of outdoor adventures.
Skating, Sledding, and Local Adventures
Stamford
Stamford is the ultimate winter playground. Mill River Park’s Cohen Skating Center is open outdoors for the season, offering public skating and rentals. For sledding, Sterling Farm Golf Course, behind the driving range, is a standout hill for fast, fun rides. Other favorite sledding spots include Cummings Park and neighborhood parks around town.
Gear up nearby: Pedigree Ski Shop is the go-to for winter apparel, boots, gloves and sleds— everything you need to make a chilly day comfortable and fun.
Tip: Pair a morning on the sledding hill with an afternoon skate at Mill River Park for the perfect family winter day.