World’s End, Hingham
This South Shore favorite boasts four hills, but your best bet is Planter’s, the large drumlin rising just before you cross “The Bar” to the far side of the reservation From the summit, zip down the footpath, or bushwhack your own descent across the broad fields.
Dexter Drumlin, Lancaster
A popular destination that draws sledders and sliders from throughout the greater Worcester area, the property’s impressive elevation and gentle contour make it a favorite with young families.
One of The Trustees’ newest reservations also boasts a terrific sledding hill, just a few steps beyond the parking lot. Its pastoral riverside location adds to the ambiance.
Ward Reservation, Andover and North Andover
At 420 feet, Holt Hill, one of three on the 695-acre property, is the highest point in Essex County. It also gives sledders a thrill, especially those who climb to the top.
The Crane Estate, Ipswich
The undulating, half-mile long Grand Allée provides some nice, family friendly sledding terrain, especially the farther east you walk from the Great House.
Stavros Reservation, Essex
Climb Whites Hill and take a breather to enjoy some terrific views of the Essex Marsh and Castle Hill. Then shove off for a slick ride back down.
Bryant Homestead, Cummington
The wide, gently sloping field located across the tree-lined drive from the main house is a perfect place to launch your toboggan. Take time to enjoy fine views of the Westfield River Valley
Bartholomew’s Cobble, Sheffield
Hurlburt’s Hill is the place to be this winter at this magical reservation in the southern Berkshires. Then warm up with hot drinks at the Visitor’s Center.