The go-to spot for all things winter, grab the sleds and bring the kids to Flagstaff Hill at Boston Common for an easy, nearby spot. There's plenty of room to spread out on this large expanse, so even when the hill is busy, you won't feel crowded. Then when you're done, head to the Frog Pond to skate a few laps around the rink. Our tip, plan a late afternoon trip so you can enjoy the holiday lights once the sun sets. The hill is located near the baseball diamond.

There's a reason this park is popular with families once the snow flies. Not only do you get sweeping view of the city skyline on a clear day, but you'll also find small slopes for newbie sledders and bigger hills for bigger kids, too. Plus, Larz Anderson Park is another two-fer spot. Come for the sledding, stay for the ice skating. Public skating sessions open at the Jack Kirrane Ice Skating Rink on December 10, 2021.

If a nearby park that's sled-ready for your tot is what you're after, look no further than Titus Sparrow Park. In the winter, little kids can bring their sleds to slide down, walk up and slide down again as many times as their little legs will carry them. Fair warning, a thermos of hot cocoa may be in order.

Rumor has it that back in the day, students used trays from the dining hall to sled down this hill. But we suggest you bring your best tube or saucer sled to glide down the slopes on this tree-lined snowy spot. The gentle slope is the right mix of thrill without too much spill (we hope!) so that everyone can enjoy it. And the haul-up factor is mild enough that most kids can do it without much help.

Long and steep is the name of the game at this park in Brookline. Plan to bring bigger kids here, or daring tots who love thrills on a snowy winter day. Watch out for trees at the bottom of the hill, and plan to stop at the nearby playground if the kiddos still have any energy left before hitting the road to head home.

What was once a landfill is now a hot sledding spot for Boston area families. After a fresh snowfall, it's the in place to be for those looking for just-right hills your kids can handle. Be sure to check out the just-opened universal playground when you're there.

You'll love Sugar Hill—it's perfect for younger kids. It's inverted so the goal is to get as much momentum to get up the other side and back down again. The slopes are gentle and you don't have to worry about kids getting near the street or plowing into a tree.

Whether or not mountainboarding was invented here, this sledding hill in Malden is sure to captivate your kids. See if they can find the seven bumps the hill is named for as they bump down the gentle grade. There's plenty of room to throw snowballs and enjoy the fluffy white stuff when you need a break from sledding too.

The Arnold Arboretum has two sledding hills to choose from and one is known as the steepest and longest in the area. This is also a great spot to go snowshoeing after a fresh snowfall.

This park is know for it's super-fun slide but in the winter the double sledding hill is the star. There's plenty of space to spread out away from other families and the kids can really get going if they start at the top.