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Sledding Spots: Trustees of Reservations

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Dates:Monday, January 15, 2024 - Sunday, March 31, 2024
Ages:Toddlers, Kids, Teens, Adults
Cost:$ see below
Category:Ice & Snow Fun
sledding spots trustees of reservations photoWith winter upon us, now’s the perfect time to visit a Trustees reservation where sliding is a downhill delight. So bundle up, head out, and let the snow – and gravity – guarantee a good time.

Some properties charge a nominal fee for entry.

World’s End
Martin’s Lane, Hingham, MA 02043
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
George Hill Road, Lancaster, MA 01523
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.

161 Forest Rd., Millis, MA 02054
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
Prospect Road, Andover & North Andover, MA 01810
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
290 Argilla Road, Ipswich, MA 01938
The undulating, half-mile long Grand Allée provides some nice, family friendly sledding terrain, especially the farther east you walk from the Great House.

View more local favorite sledding spots near Boston

Stavros Reservation
Island Road, Essex, MA 01929
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
207 Bryant Road, Cummington, MA 01026
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
105 Weatogue Road, Ashley Falls, Sheffield, MA 01257
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

Downhill skiing is another great way to get outdoors and explore trails covered with snow.  Visit our guide to Skiing Near Boston to find some terrific Ski Resorts near you.

If downhill skiing isn't your thing, snow tubing or cross country skiing is another option to get out into the wilderness, and explore trails covered with snow. 

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