Enjoy the Wonders of the Winter Outside

Posted by Massachusetts Office of Travel & Tourism

by Paul Jahnige, Director, Massachusetts Office of Outdoor Recreation

Some of my best and most memorable experiences outside in Massachusetts have been in winter! 

Some of my worst and most memorable experiences outside in Massachusetts have been in winter! 

Winter is an amazing (and necessary) time to play outside, especially with family. Snow forts, sledding, skating, snowmobiling, and for the more adventurous – mountaineering, polar bear swimming, ice climbing, and back-country skiing. There is something so special about the quietness, the crisp air, slipping and sliding, and embracing the cold.  

But enjoying the Massachusetts’ winter wonderland takes preparation, planning, and practice to ensure a good time, otherwise, winter fun can turn sour, especially for kids. Here are a few tips for making the most of winter in Massachusetts, and some recommendations for activities and places to get started with your family. 

5 Tips for a Successful Winter Adventure with Family 

Make a Plan, but Be Ready to Amend the Plan: Getting outside in winter always benefits from some basic planning. Choose an adventure that is right for your family. In winter, err on the side of easier. Call or research ahead to make sure the location is open, the trailhead is plowed, the snow conditions are good, etc. If you are going on trail, make sure you know the route and have a map. Getting lost in the snow is not fun. 

BUT, in winter and with kids it is important be ready to amend the plan if needed. Check in with everyone frequently. Monitor fingers and toes. Don’t be afraid to cut your adventure short and go find some hot chocolate or warm soup. You’ll be thankful you did. 

Layers, Layers, Layers: You have probably heard this, but it bears repeating over and over. Dressing for winter fun is vital, and that involves layers. Layers don’t have to be fancy or expensive (although you should avoid cotton in favor of synthetics or wool if possible). Three light layers are better than one thick one. Maintain your warmth by shedding or adding layers as needed (or even better, just before needed). Remember, there is no such thing as bad weather, just inadequate layer management.  

Bring Food and Water: Adventuring in winter burns calories, so be prepared by bringing some extra food, bars, snacks, nuts or a lunch thermos with something warm. You’ll be pleased you did. Also, hydrate! Drink before you head out, and bring water along. Being well watered will actually make you warmer.  

Include Warmth in your Plan: This may seem like an odd tip for getting out in winter, but warmth can be a wonderful part of cold weather fun. I have hand warmers and toe warmers in my “go” bag. If the location you are visiting has grills or allows a campfire bring wood, paper and matches. If you are at a site with a lodge, take advantage of it. Embrace the cold, but also embrace the warmth. 

Mind the Thermometer: When we think of winter in Massachusetts, we think of cold. But sometimes we forget that there is cold (moderate cold), and then there is cold (severe cold). Either can be fun for an outdoor adventure, but temperatures below about 20 degrees (f) require extra planning and preparation.  

Suggestions for Winter Adventuring with Children 

Pick a Known Hike, ideally one with a nice view, and pitch this as a winter adventure to your kids. Good winter hike options in Massachusetts might include: 

South of Boston: Hike Great Blue Hill, Buck Hill or another trail at DCR’s Blue Hills Reservation in Milton. You can find various options here. 

North of Boston: Try the Reservoir Trail or Rock Circuit Trail at DCR’s Middlesex Fells. Find suggested hikes here. 

Central Mass: Charlie’s Loop at Purgatory Chasm State Reservation in Sutton, or the Wapack Trail at Mount Watatic in Ashburnham both offer something special. 

Connecticut River Valley: Mount Tom State Reservation offers amazing views of the valley, and a variety of fun trails. 

The Berkshires: Greylock Glen in Adams is the gateway to Mount Greylock State Reservation and the state’s highest peak. The Glen has a variety of winter hike options to suit every taste.  

When it Snows… You Goes! The best time to enjoy winter in Massachusetts is during or just after a fresh snow. Change plans, take a mental health day, put on the layers, lace up the boots, and get outside with your family. Make it as simple as that.  

Embrace Sliding! Whether its skiing, tubing, skating or just plain sledding, the best thing about winter is the feeling of freedom found in gliding and sliding. Embrace your inner youth and enjoy it as a family. Check out these resources: 

The Trustees of Reservations offers these sledding spots! 

DCR hosts ice rinks around the state, and also offers adaptive skating opportunities. 

Many of Massachusetts Ski Mountains also offer Tubing Parks! 

Consider starting a local Free Sled Library like this one in Pittsfield. 

Finally, Try Something New with Friends and/or Guides: Want to introduce your family to back-country skiing or snowmobiling or ice climbing or dog-sledding? Trying a new outdoor activity, especially a winter activity, can be daunting. The best way to try out something new, is with guides – be they friends who participate in the sport, club volunteers, or professional guides. Perhaps the below ideas will spark your imagination: 

Here is a list of guides and clubs in the Berkshires, including ski and snowmobile clubs.  

Adventure Guides like Guineafowl Adventure or Adventure East offer a variety of winter adventuring options. 

Always wanted to try dog-sledding? Check out Hilltown Wilderness Adventures. 

Most ski centers offer lessons and rentals, find out more here, and for cross-country skiing lessons near Boston visit the Weston Ski Track. 

Most importantly, get out, and enjoy the snow! 

TOPICS: Adams, Ashburnham, Hiking, Hilltown, Massachusetts Office of Outdoor Recreation, Milton, Mount Greylock, Pittsfield, Sutton, Weston, Winter Sports