Begin with a nighttime train ride aboard the Naugatuck Railroad’s Northern Lights Limited, leaving from the railroad station in Thomaston. The cars are festooned with lights both inside and out on this journey to Santa’s Train Workshop, where Santa himself hops aboard and greets everyone.
Connecticut’s winters are at their deepest in its Northwest Corner, where the high hills are often snow-covered, sleighs maneuver over the river and through the woods, and Christmas trees await your approval.
Loon Meadow Farm
Next day, it’s a drive up to Norfolk, also known as “Connecticut’s Icebox,” where the snow falls first and lasts longest. While there, head out to Loon Meadow Farm, where hayrides, carriage rides and even sleigh rides can be arranged, according to weather conditions.