Embracing Winter Activities in New England

Winter in New England is not something we wait out. We embrace it. Our family is a ski and snowboard crew, and cold weather usually means heading north for time outdoors together. We have been going to Okemo Mountain Resort for years, and it continues to be one of our favorite family-friendly ski mountains in New England. The terrain works well for all levels, the ski school is excellent (my dad is an instructor), and the mountain does a great job making winter fun for both kids and adults. In addition to skiing and riding, Okemo also offers tubing, which is always a hit. While it does not have a true village, there are solid local dining options and the Spring House, which includes a gym, an indoor pool, a dedicated kids pool, and a great place to warm up and unwind after a day outside.

Living in Andover puts us in an ideal location for winter activities in New England. Within about a two hour drive, there are countless ways to enjoy the season, whether you are planning a ski weekend, a day trip, or a low-key winter outing close to home.

Below are some of our favorite winter activities and destinations, all easily accessible from northern Massachusetts.

Best Skiing and Snowboarding

If your family enjoys skiing or snowboarding, New England offers incredible variety within a short drive.

Okemo Mountain Resort, Ludlow, VT
A longtime favorite for our family. Wide trails, reliable snowmaking, tubing, a strong ski school, and family-friendly amenities make it an easy choice year after year. The Spring House pool is a huge bonus, especially with kids.

Gunstock Mountain Resort, Gilford, NH
A great option for a day trip from Andover. Gunstock offers lake views, night skiing, and terrain that works well for mixed ability groups.

Waterville Valley Resort, Waterville Valley, NH
A classic New Hampshire mountain with a walkable village feel, making it easy to combine skiing with dining and downtime.

Pats Peak, Henniker, NH
Perfect for beginners and younger skiers. Smaller, approachable, and ideal for families looking for a relaxed ski day.

Snowshoeing and Winter Hiking in Massachusetts and New Hampshire

You do not need skis to enjoy winter outdoors in New England.

Harold Parker State Forest, North Andover, MA
Close to home and incredibly peaceful in the winter. A great option for snowshoeing or quiet walks after a snowfall.

Mount Monadnock, Jaffrey, NH
Best for experienced winter hikers. Challenging but rewarding, with incredible views on clear days.

Great Brook Farm State Park, Carlisle, MA
Flat, scenic trails that work well for snowshoeing and winter walks.

Ice Skating and Winter Strolls Near Boston, MA

Sometimes the best winter activities are simple and close to home.

Boston Common Frog Pond – Ice Skating, Boston, MA
A classic winter activity that is fun for kids and visitors alike.

Salem, MA
Much quieter in the winter, making it a great place to walk, shop, and enjoy a meal without the crowds.

Rockport, MA
Cold but beautiful. Winter by the ocean has its own charm, and Bearskin Neck is far more relaxed this time of year.

Cozy Winter Getaways Within Two Hours of Andover, MA

If your idea of winter fun includes great food and a slower pace, these towns are perfect.

Portsmouth, NH
Charming year-round, with excellent restaurants and waterfront walks that feel especially cozy in winter.

Stowe, VT
A bit farther, but still doable. Skiing, shopping, and that classic Vermont winter atmosphere.

Woodstock, VT
Quiet, picturesque, and ideal for a peaceful winter weekend away. It also has great shops, and fun fact, I used to work at The Woodstock Inn & Resort.

Winter in New England offers a lifestyle that is active, seasonal, and deeply connected to the outdoors. From ski weekends and snowy trail walks to coastal towns and cozy village getaways, there is so much to enjoy when you live in the right place. Being north of Boston makes it easy to take advantage of everything the region has to offer without long drives or complicated planning. It is one of the reasons so many families love calling this area home and why winter here feels less like something to get through and more like a season to enjoy.