This Month’s Featured Article


By Published On: December 1st, 2023

We all have love-hate relationships with aspects of the seasons, and so it goes with me and winter. My hesitation is brief when asked if I like winter. “No!” I exclaim. “It’s cold, it’s dark, and it seems to last forever.” And snow? If I see a flake in the forecast I shiver with worry about driving anywhere. My brothers know I don’t venture north to see them in Vermont or Maine starting in November and going until April, sometimes May to be on the extra-safe side. I’m a wimp, I know.

But there are times when I really love winter. One of them is when the snow is falling and I know that no one in my family has to travel in it. We are all in warm, safe places with the provisions we need. There’s a magical silence to snowfall that is perfect for rest, reflection, and baking. The second time I really love winter is when the snow has stopped and enough has fallen to go sledding. I love sledding. Once the necessary pathways are shoveled, I grab a sled and head for a hill. 

I was lucky to grow up in Chester County, PA, where there were lots of great sledding hills and kids from several families would get together and make a day of it, sharing Flexible Flyers and toboggans and out-of-control saucers. The thrills and spills we shared were, for me, more fun than any amusement park rides. My kids know this about me: If the conditions are decent, we’re going. When they were little I’d bundle us all up in snow pants and boots with hats and waterproof gloves and lots of layers, grab whatever sleds were in the attic or barn or garage, and find a hill.  Luckily, the property where I raised my boys in Ghent, NY, included a few good slopes, but when the roads were clear we would also drive to join people at a park with a great hill. 

Who knows how much snow we’re going to get this winter, but my advice is to be ready to enjoy it with the simple and sensational experience of sledding. 

The sled

Do you already have a sled? Take a look at it and check for cracks or missing rope handles you need for pulling it up the hill behind you. Even small cracks in the hard plastic will ruin the ride. Sad, but true. 

I did a Google search for best family-friendly sleds to see what the latest types and designs are, and I wasn’t surprised to find one from L.L. Bean at the top of several lists. It’s the Polar Slider DLX. It’s on my wish list for Christmas!

The gear

Another thing you’ll need is the right clothes. Snow pants are a must. Boots and gloves that are waterproof and warm. A good hat that covers your whole head and ears. Sledding will shoot snow into your face as you zip down a hill, and if you put your feet out to use them as brakes, you’ll also get snow in your face. Bailing out at the bottom of the hill or even falling off at some point while you’re going down puts more snow in your face and in the spaces between your coat and gloves. Fortunately, the exercise of going up the hill warms you up so much that the snow can feel good. 


If you’re going to be sledding for a while on a particular hill, bring a water bottle – or two! Sledding is good exercise, and you’ll get thirsty. It’s nice not to have to worry about your water getting warm. Just be sure to put your name on your water bottle so it doesn’t get mistaken for someone else’s. If there are several of you out sledding together and you want water bottles and maybe cider donuts or another energizing snack, you could bring a small cooler to have them together in a container that’s easy to carry. Remember, be conscientious and don’t litter on the hill, no matter what!

Where to go

I did a Google search for best sledding spots in the counties served by Main Street Magazine. I was delighted to find there are quite a few. Here are some top spots. I suspect that if you’re a sledding aficionado like I am that you know some others. Please share! Hope to see you on a sled this winter – but not too often!

Oh, and another great part of sledding? Coming home and making hot chocolate and buttered toast, getting into comfy clothes, and enjoying a fire in the fireplace.  

Sledding in Dutchess County

Just a couple of miles from downtown Rhinebeck is Drayton Grant Park at Burger Hill (3158 NY 9G), a wonderful spot any time of year, and home to a hill that’s over 500-feet high and arguably one of the best sledding spots in our sled-happy area. If there’s snow to cover it, you’ll find folks of all ages sledding on Burger Hill. While it’s big, it’s not crazy steep, so you don’t get the speed demons whizzing by the rest of us. There’s a nice, big flat spot at the bottom for lazy landings and great views of both the Catskill and Berkshire Mountains in the distance when you get back to the top. 

If you’re anywhere near Wappingers Falls, you have to check out the sledding at Bowdoin Park. The park is located at 85 Sheafe Road on the banks of the Hudson River. It covers over 300 acres, and is another all-season gem, with everything from a great playground to a disc golf course, hiking trails with amazing views, a picnic pavilion, convenient restrooms, and a wonderful sledding hill! Sledders find their own grooves there, from the whizzers-by to the wanderers. Hay bales at the bottom assure that stopping is safe. 

Not far from Rhinebeck is Staatsburgh, where the Mills Mansion was built in 1832 on a premier property on the banks of the Hudson River. The Mills, like their neighbors the Rockefellers and Vanderbilts, were a wealthy family that built spectacular mansions in the Hudson Valley. Today the stunning Greek revival home is a tourist attraction lovingly preserved by the Friends of Mills at Staatsburgh. And it just happens to have a great hill behind the house sloping toward the river. It’s a long and gentle hill that, fortunately, slopes up at the bottom so you don’t have to worry about sailing off into a hedgerow or the mighty Hudson itself. It’s fun to imagine the families of these Gilded Age icons dressed in their winter clothes sledding on these same hills. 

Don’t overlook Thomas Boyce State Park in the hamlet of Wingdale near Dover. This is a park for people of all ages – it got a new playground installed recently, and there are batting cages and picnic spots. In the winter, you can enjoy the grounds for skiing or snowshoeing, and the hills are perfect for some easy sledding. The park does have some steep parts with great views – it housed a now defunct hang-gliding launch site – but for sledding and snow sports, stick to the gentler slopes in the main area. 

Sledding in Columbia County

Columbia County is known for its diverse topography, ranging from near flat lands along the Hudson River to steep hills toward and as part of the Catamount Mountain range (where Catamount Mountain Resort is located just over the ColCo border on the Massachusetts side). Oddly, the only publicized sledding spot in the county is the hill at Siegel Kline-Kill in Ghent, NY.

Siegel Kline-Kill is one of several wonderful and well-maintained recreation areas overseen by the Columbia Land Conservancy. The park is deceptive in that for the most part it’s a flat space that’s great for dog-walking, jogging, and quiet contemplation. But it has a serious hill that’s a short walk from the parking lot. It’s not long, but it’s steep and fast. Older kids and thrill-seeking adults are its biggest fans. If you’re going with little ones, you can stick to the lower part of the hill. There’s an extended flat area for coasting to a comfortable stop. 

Clermont State Historic Park in Germantown in southwestern Columbia County is a great place to admire the Hudson River, and it has gently sloping hills that are nice for sledding. 

Sledding in the Berkshires

Western Massachusetts is called the Berkshires because of the Berkshire Mountains, which run north to south along its western border. Suffice to say there are some great hills in the Berkshires, and sledding is popular there.

A favorite place for families looking to enjoy the outing with children of various ages is Clapp Park in Pittsfield. The expansive sledding hill is adjacent to a large parking area, making it easily accessible. The hill is steep enough, but not too steep. The snow gets packed with all the use, so it’s enjoyable at many different spots. It’s at 233 West Housatonic Street. 

The more adventurous (and older) hightail it to hilly Williamstown, home of such cultural icons as Williams College and the Clark Museum. It’s also home to Williamstown Rural Lands, a conservation trust organization headquartered at Sheep Hill, a former dairy farm known as Sunny Brook Farm, located at 671 Cold Spring Road. Several of the farms buildings are still on the 52-acre property, and they now house interactive exhibits about life on the farm. Sheep Hill is so-named for the sheep that once grazed its steep slope. Sightseers and tourists enjoy it year-round, and serious sledders visit when there’s enough snow. 

A little farther south in the Berkshires, there are sledding hills at Tanglewood, and also at Monument Mountain Regional High School in Great Barrington.

Sledding in the Litchfield Hills

There are several parks in Litchfield County in northwestern Connecticut. Many of them are forested, and while they offer great hiking and cross-country skiing, it’s hard to find a sledding area that’s accessible to the public. I imagine there are some sledding hills around the Hotchkiss School in Lakeville, but I couldn’t find anything online. 

Sledding in Putnam County

If you want to make a day trip for sledding and outdoor winter fun, head to Fahnstock Winter Park in Carmel. It’s a 16,000-acre park featuring a “winter park” with an elevation of 1,100 feet. Fahnstock’s Winter Park offers nearly ten miles of groomed and mapped trails for skiing and snowshoeing, plus a sledding hill. Rentals of baby sleds and snow tubes are available for the sledding hill, and rental skis and snow shoes are available for the trails. For hungry and thirsty snow lovers of all ages, there’s a concession stand that sells hot chocolate and other hot and cold food and beverages. The restrooms are clean and comfortable, with room to change. 

Knowing all these options are in our area is inspiring! I’ll wait for the snow to stop and the roads to be clear before heading out to spots that aren’t that close to me, but I know I’ll enjoy them when I get there. I may take my grandson, too. He’s three and should love it. Convincing his dad, my son, to join us will be the more challenging part, as he knows only too well how I will go up and down a hill for hours before I retreat to the indoors. 

Do I like winter? “No!” Do I like sledding? Yes, yes, a thousand times yes! If you know of some good hills in your area, please share them with the magazine and they’ll be posted on the website. Thank you! •