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Get Out and Embrace Winter: Where to Hike, Walk, Ski, Skate and Snowshoe By Region

Winter Fun

BOSTON & GREATER BOSTON

Governor Hutchinson’s Field, Milton
Take in views of the Boston skyline and Boston Harbor Islands on an easy, wintry walk at this stunning hilltop reservation, once the home of the last royal Governor of the Massachusetts Bay Colony. It’s also a great place to get your blood pumping with some cross-country skiing, snowshoeing and sledding.
   
Rocky Woods, Medfield
Logging roads initially laid out two centuries ago continue to fulfill their transportation roles – but today for easy walking, cross-country skiing, and snowshoeing in the winter on this beautiful 491-acre property. The route around Chickering Pond and the Bridle Trail loop are both ideal for families with young children, and are stroller friendly without snow. Snowshoe rentals and ice-skating are available on weekends.

Francis William Bird Park, Walpole
This 89-acre, historic landscape park offers three miles of flat pathways, which meander past grassy meadows and tranquil duck ponds, through woodlands, and over stone arch bridges spanning trickling streams. Ideal for walking as well as snowshoeing and cross-country skiing, the park also includes a recreational area and children’s playground.

World’s End, Hingham
This South Shore favorite with panoramic views of Boston’s harbor and skyline features four hills that are great for all kinds of winter fun, including Planter’s, a large drumlin rising just before you cross “The Bar” to the far side of the reservation, which is perfect for sledding. Frederick Law Olmsted-designed carriage paths throughout the property that offer opportunities for all ages to enjoy moderate hiking, snowshoeing, and cross-country skiing at this spectacular Hingham haven.

Governor Oliver Ames Estate, Easton
Set in the quiet town of Easton 30 miles outside of Boston, the historic 36-acre Governor Oliver Ames Estate features rolling hills, meadows, ponds, and a host of lovely and mature trees, as well as remnants of a storied and prominent past – all within walking distance of the North Easton National Historic District. The gentle hills are ideal for sledding with young children. A gravel driveway, which dissects the property, leads all the way down to the bridge at the river and offers easy opportunities for strolling, snowshoeing, and cross-country skiing. 

The Old Manse, Concord
Built in 1770, this National Historic Landmark became the center of Concord’s political, literary, and social revolutions over the course of the next century. The handsome Georgian clapboard building sits near the banks of the Concord River among rolling fields edged by centuries-old stone walls and an orchard overlooking the North Bridge where the historic Battle of Lexington and Concord took place. A short network of footpaths (also a link in the Bay Circuit Trail) provides a scenic setting for an easy winter walk or snowshoe.

Chestnut Hill Farm, Southborough
Rolling fields and woodlands, stone wall-framed pastures, and freshwater wetlands make this scenic working farm a perfect place for winter recreation and exploration. Grab cross country skis or snowshoes or just explore the 131-acres by foot. Chestnut Hill Farm is one of the last remaining farms in Southborough Chestnut Hill Farm and has a Community Supported Agriculture program.

Eleanor Cabot Bradley Estate, Canton
This picturesque, 90-acre country estate offers three miles of woodland paths and trails that meander around a stately house and gardens, open fields and pastures. The property is a picturesque place to enjoy winter walking, gentle cross-country skiing, and snowshoeing.

Norris Reservation, Norwell
This scenic reservation located on the banks of the tidal North River is a recreational wonderland tucked into the suburb of Norwell traversing 129 acres. Ideal for easy winter walking and beginner snowshoeing, you can chose from a number of short in-and-out or longer trails that meander through a pristine forest scattered with white pine and oak.

Weir River Farm, Hingham
This iconic, 75-acre working farm features a myriad of trails that connect to Whitney and Thayer Woods and Wompatuck State Park, the largest contiguous tract of open space on the South Shore. Enjoy winter walks and cross-country skiing through woodlands and open meadows, soaking in beautiful views from the top.

Powisset Farm, Dover
This working farm, revived as the site of a Community Supported Agriculture program has a history of agriculture dating back three centuries! Its welcoming, easy trails are open year-round. Take the loop trail beyond the cultivated land to the upland oak forest to see the pair of brooks and views of the croplands and open fields.

NORTHEAST

Appleton Farms & Appleton Farms Grass Rides, Ipswich and Hamilton
America’s oldest continually operating farm, and its adjacent Appleton Grass Rides, both span over 250 acres, providing an ideal setting for winter recreation.  Take a winter walk, snowshoe, or Nordic ski on over five miles of carriage paths. On weekends, warm-up afterwards in the visitor center with a hot drink, followed by a tour of the historic farmhouse. Appleton Farms also offers year-round cooking classes and programs for all ages.

Castle Hill on the Crane Estate, Ipswich
The undulating, half-mile long Grand Allée on Castle Hill, a National Historic Landmark, provides some great family-friendly sledding terrain, especially the farther east you walk from the Great House. Stroll through the recently restored Casino Complex nestled in the hills of the Allée and enjoy spectacular views of Cape Ann and Crane Beach on your way down. The Great House is closed for the season and reopens in the spring, but the grounds are open year-round and perfect for hiking, snowshoeing, and cross-country skiing.

Ravenswood Park, Gloucester
Miles and miles of meandering carriage paths offer the winter explorer fresh tracks and a few surprises on a wintry day. On weekends and holidays, let the Cape Ann Discovery Center—which offers snowshoe rentals, hands-on nature exhibits, and discovery backpacks—be your jumping off point. When it’s time to thaw, warm your toes by the woodstove with a hot cup of cocoa.

Ward Reservation, Andover and North Andover
At 420 feet, Holt Hill, one of three on this 695-acre property, is the highest point in Essex County offering superior sledding and spectacular views extending from the surrounding Merrimack Valley to the Boston skyline. Chose from nearly 10 miles of trails to explore, including the Red Trail loop, which is ideal for cross-country skiing and snowshoeing

Farandnear, Shirley
This idyllic locale was named by its original owner, professor Arthur Banks, for both its feeling of remoteness and the convenience of its location: only 2 days journey by horse from his primary home in Wollaston. The beauty of Farandnear will carry you away with park-like grounds, wooded trails, and open fields.  Enjoy the open-air Visitor Center Pavilion that opened this fall and features an interactive nature wall and outdoor fire pit. Snowshoe beneath the bough of diverse conifers at the site’s pinetum. Rentals are available on select Sundays and excursions followed by hot cocoa in the Pavilion will take place throughout the winter months.

SOUTH COAST

Lyman Reserve, Bourne
For a winter hike, snowshoe, or cross-country ski outing off the beaten path, choose from two trails offering spectacular views of Buttermilk Bay and the Cape Cod railroad bridge at this spectacular place.  Situated at the mouth of 4.5-mile-long Red Brook on Buttermilk Bay, Lyman Reserve features a 1.5-mile loop to Red Brook meanders through a pine forest that leads to a sandy beach. The shorter .25 mile trail is perfect for families with young children looking to get out and explore winter’s wonders.

Allen C. Haskell Public Gardens, New Bedford
A network of cobblestone paths lined with rare and exotic trees make this six-acre property featuring one of the oldest houses in New Bedford seem like a country estate in the heart of the city. The site of the former, famed Allen C. Haskell and Son Nursery, the Haskell Public Gardens is a great place to stroll, cross-country ski, snowshoe, or pull a child on a sled. Yet, you need not wait for the first snow to fall to visit New Bedford’s newest park, the grounds are inviting and beautiful to visit every day of the year.

CENTRAL & WESTERN MASS

Notchview, Windsor
It just wouldn’t be winter without snowshoeing and Nordic skiing at Notchview, a true gem when the snow flies. With more than 3,000 acres of rolling terrain and almost 40km of trails – from groomed to backcountry – Notchview is the idyllic escape for any winter enthusiast.  A café, lessons, and equipment rentals make this property the perfect place for beginners and experts alike to learn and challenge themselves before warming up in the Visitor’s Center to recount the day with family and friends. And, Notchview’s small but dedicated award winning, all-volunteer Ski Patrol is on hand to help with everything from equipment malfunction to helping new skiers get accustomed to the terrain.

Bartholomew’s Cobble, Sheffield
A National Natural Landmark located in the beautiful southern Berkshires, Bart’s Cobble is always abuzz in winter, becoming a snowy playground with plenty of fun and fascinating events for all ages. After sledding on Hulburt’s Hill or touring the cobbles and following wildlife tracks, warm up with hot drinks and friendly staff in the Visitor’s Center.

Tully Lake Campground, Royalston
Enjoy an off-season exploration of this close-to-Boston campground, where you might spy tracks of moose and coyote or the secretive bobcat or fisher. Set along the shores of a 200-acre lake, there are miles of hiking trails that lead to scenic overlooks and roaring waterfalls.  Enjoy a wintry hike and look and listen for an owl’s hoot or the staccato of a nearby woodpecker.

Monument Mountain, Great Barrington
This popular peak is great for invigorating winter hiking, but recommended for the fit and experienced hiker. Stunning views of the Southern Berkshires and Housatonic River Valley blanketed in snow await you at the summit.

Mount Warner, North Hadley
The gentle slopes of this woodland hill overlooking the Connecticut River Valley stand amid a 500-acre swath of protected land. The old cart paths and wood roads of this land’s logging and farming past make for great snowshoeing, sledding and cross-country skiing. Explore the newly constructed Salamander Trail Loop which intersects these paths as it ascends through oak and beech trees to reach the evergreen groves further upslope.

Bullitt Reservation, Ashfield
This beautiful blend of fields and farm buildings, mixed woodlands, and streams forms a crucial link in almost 3,000 acres of protected land. Take the family here for a long winter walk, snowshoe or cross-country skiing outing this winter and keep an eye out for the deer and other wildlife that call it home!