Worcester is lucky enough to have two ski resorts within a short distance of the city center. Ski Ward (skiward.com) is just five miles away in Shrewsbury, and has no less than nine trails serviced by five lifts. It also has a five-lane Tuba Slide area, terrain garden and learning pipe, and a Fireside Lodge with a snack bar at the foot of the slopes. Just 15 miles to the north of the city is the ski area at Wachusett Mountain (wachusett.com), where two lifts, a carpet, t-bars and a triple serve the dozen or so trails.
Northern Exposure Outfitters (ne-outfitters.com) in Brookfield, 15 miles to the west of Worcester along Route 9, offers a Dog Sled Experience session in wintertime. More than 60 inches of snow fall here during a typical season, so there's usually plenty of opportunity to try this out. You can experience a dog sled ride that's customized to meet your individual needs and includes helping the musher hook up the dogs to the sled.
Worcester's Ecotarium Museum (ecotarium.org), located just a mile east of the city center, opens its extensive grounds during the snow season to visitors who'd like to try their hand at snowshoeing. Novices and veterans will enjoy views of the snow-capped trees and iced-over ponds, and will even get to see an Arctic polar bear, otters and a red fox or two. When the weather's right, you can bring along your skates and enjoy skating on the upper pond.
For a fun evening in wintertime that will result in memories of something out of the ordinary, try out one of the Salem Cross Inn's (salemcrossinn.com) dining events. You can see your colonial style prime rib roasted in front of a roaring fire as it's turned on a spit, or give the chowder a stir in its cast iron pot. Other dining events include murder mystery dinner theaters and carolers during the Christmas season. The inn is located in West Brookfield, just a few miles west of Worcester.