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13 Fun Winter Destinations

Snowy winter in Massachusetts

Although many associate the winter season with endless shoveling of snow and frigid temperatures, winter is also a great time of the year to participate in fun & festive winter themed recreational activities. Instead of thinking of snow as a burden, take advantage of the opportunity to try out a new sport (snowshoeing, cross country skiing, and ice skating to name a few).

Listed below are 13 wonderful destinations for the winter season. Some destinations are urban areas which offer an abundance of winter themed recreation and holiday events, while others are cozy, hidden gems, far away from any civilization. One thing’s for sure – each area offers its’ own unique attractions, activities, and above all, a beautiful, festive winter setting.

Take a look at my featured winter destinations and feel free to share some of your own suggestions in the comments below.

1. The White Mountains of New Hampshire

A snowy day at Nestlenook Farms in Jackson, New Hampshire

The White Mountains, part of the northern range of the Appalachians, is the perfect getaway for city dwellers who are craving some much needed peace and quiet. The region is a popular year-round vacation destination due to its’ close proximity to cities like Boston and New York. The area is home to many quaint towns and villages which offer an idyllic setting for winter and holiday visits. Most towns in the mountains get plenty of snow, opening the door for endless seasonal fun. Listed below are a few fun areas and activities to consider on your next White Mountain vacation.

Jackson, New Hampshire

Jackson is a tiny town (population just over 800) in the White Mountains Region area. It is a very popular vacation destination due its’ proximity to great area attractions, abundance of desirable seasonal activities, and secluded location. The beautiful covered bridge as you enter the town is a wonderful photography opportunity, especially during the scenic fall and winter seasons.

Covered bridge in Jackson, New Hampshire

Top Winter Activities in Jackson

*Sleigh rides & Ice skating at Nestlenook Farms

Visiting Nestlenook Farms is like taking a walk through a holiday snowglobe. At this snowy 65 acre resort, you will have the opportunity to take a horse drawn carriage ride around the beautiful property, which is surrounded by incredible views of the White Mountains. Wrap yourself in a blanket, grab a hot cocoa, and enjoy the winter wonderland around you.

Snowy horse drawn sleigh ride in New Hampshire

After your sleigh ride, head over to the 3 acre Victorian Ice Rink for a wonderful afternoon of skating alongside snow capped mountains. Old fashioned chime music, beautiful holiday decorations, and views of the Austrian sleigh rides passing over the bridge create an incomparable wintry setting. Take a break with a warm cup of cocoa by the fireplace in the warming hut.

Ice skating at Nestlenook Farms in Jackson, New Hampshire

*Cross country skiing and snowshoeing

With beautiful mountain views, charming architecture, and the sights and sounds of nature all around you, Jackson is the ideal place to embark upon a skiing adventure. Jackson Ski Touring Foundation offers rentals and lessons for beginners.

Bretton Woods

Cross country skiing at Bretton Woods Nordic Center in New Hampshire

Bretton Woods is an area of the White Mountains known for its’ great ski resorts. Mount Washington Resort is a popular winter destination due to its’ prime location on the grounds of Bretton Woods Nordic Center, one of the largest cross country skiing destinations in the US. As you enjoy the variety of trails, whether by skis or snowshoes, you will be treated to pristine snowy views of the beautiful White Mountains National Forest.

Bretton Woods is the largest ski area in New Hampshire, with 62 trails and 3 terrain parks. They also offer night skiing, so you can continue on as long as you like.



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