This New England Town Comes To Life In The Winter With Fun, Quirky Activities

Set against the picturesque backdrop of Berkshire County in Massachusetts, the charming town of Stockbridge is a wintry wonderland of activities when the snow begins to fall. Located in the western part of the state, the city's historic architecture and surrounding woodlands create a charming picture of a small New England community. Despite its small size, Stockbridge offers many whimsical ways to spend a chilly day, such as tubing down a snowy mountain, taking a snowshoe trek across a frosty orchard, or stepping back in time to help the city recreate a famous painting on Main Street.

Winter activities abound in Stockbridge, especially at an outdoor resort such as Bousquet. In addition to skiing and snowboarding, Bousquet offers several options for the whole family, such as vacation camps, racing leagues, and the popular Tube Town. For those who enjoy riding an innertube down a slippery mountainside, the resort provides 10 tubing lanes and a carpet lift to bring tubers back to the top of the trail. Special activities like night snow tubing are also offered. The resort can generate snow on the course to guarantee 100% coverage, so the adventure never stops even if the snow hasn't fallen that day. Bousquet also provides fire pits and cabanas for visitors so that they can relax and warm up in between tubing.

Enjoy snowshoe treks and hot cider

One of the reasons that Stockbridge is named one of the most magical winter towns in the U.S. is because of a town landmark, according to Trips to Discover. The Red Lion Inn is one of the oldest inns in America, and it has been operating continuously since 1773. The hotel's charming front porch and antique-filled rooms offer guests delightful accommodations while they launch out on adventures that the hotel can arrange, such as guided cross-country ski tours or snowshoe day trips. Afterward, they can return to the inn and swim in the outdoor pool that is heated year-round.

Hilltop Orchards is another destination near Stockbridge that offers a variety of ways to enjoy the wintry weather. The farm is over 100 years old, with a cidery operating on the premises. Begin a visit with a snowshoeing trek across the 200-acre orchard and along the wooded pathway. When you reach the trail's peak, you'll be able to enjoy the scenic panorama that overlooks three states. After the hike, it's time to step inside and enjoy the fruits of your labor. The farm produces its own apple cider which is a perfect accompaniment to their homemade apple cider donuts. Hilltop also offers a tasting room for adults, featuring selections from their specialty ciders and wines. They encourage visitors to choose their favorites, and then relax by the wood-burning fireplace and watch the snow fall across the orchard.

Recreate Stockbridge Main Street at Christmas

One of America's most beloved artists, Norman Rockwell spent over 47 years illustrating the covers of "The Saturday Evening Post" with everyday images of family life, childhood mischief, and young love. These scenes were depicted with a warmth and familiarity that resonated with the magazine's readers. Rockwell lived in Stockbridge for the last 25 years of his life, and this picturesque New England town became the backdrop for many of his paintings, showcasing the beautiful landscape views and architecture of this part of the country. The Norman Rockwell Museum in Stockbridge is dedicated to the artist and celebrates his contribution to American history. Visitors to the museum can enjoy 323 of Rockwell's covers of "The Saturday Evening Post," as well as current exhibitions, such as "Norman Rockwell: Winter Wonderland."

One of his most beloved paintings is named, "Stockbridge Main Street at Christmas," a lovely illustration of how the city looked during the winter in the 1950s. With busy Christmas shoppers passing quaint storefronts and vintage automobiles, the original painting is eight feet long and hangs in the museum. The town celebrates this imagery during the first weekend of December every year, when Stockbridge closes off traffic in the center of town and travels back in time to recreate this scene. The annual event is a celebration of Stockbridge and its place in history, with antique cars, Victorian Carolers, and horse-drawn wagon rides to complete the celebration of this charming town.