It's important to get your second home ready for winter. Photo: Patrick Tomasso on Unsplash

President John F. Kennedy is credited with saying, “the time to repair the roof is when the sun is shining.” That was in 1962, when Kennedy was urging Congress to appropriate funding for his favorite programs.

I think of that quote every year around this time, when winter is approaching and our second home presents all sorts of opportunities to spend money on cold-weather prevention and precautions. Following Kennedy’s advice, we should be preparing and fixing – and spending money – before the temperatures plummet and the snows fly.

The temptation, of course, is to hold off on prevention and precautions for problems we don’t have yet – and maybe won’t ever have. 

Maybe it will be a mild winter. Maybe the pipes won’t freeze. Maybe there won’t be a lot of snow on the roof. Maybe mice won’t come into the house this year. Maybe that stone wall will hold up another year. 

Or maybe it will be a particularly cold and snowy and blustery winter, and we will be wishing we’d spent some money in the autumn to keep us from spending a lot more to repair damages that we might have avoided.

From our own experience, and from checking with other much more authoritative sources, here are some suggestions for prepping for winter, whether you’ve got a year-round house or a summer place that you lock up in the autumn and don’t open back up til springtime.

Our weekend and summer house up the Hudson Valley got only a few inches of snow last winter, and the temperatures rarely got below freezing. But we’ve had some winters with several feet of snow and extended periods of temperatures down into single digits, when we can ski and skate on the lake for weeks at a time. 

We’ve avoided any major problems, partly through luck and partly through preparations. Most of those preparations were not due to our own brilliant advance planning, but rather to the considerate checklist presented every winter by our “guy,” Kevin, our all-purpose, year-round handyman, carpenter, painter and more. (See my previous Escape Home piece, “You Gotta Have a Guy.” 

Kevin gives us a written list, and that’s a starting point for our discussions with him on winter prep. His list includes plans to plow our driveway for minor storms (three to five inches) for $50 and major storms (six or more inches) for $70. He’ll check our insulation, and plug any drafts. He’ll replace any of the house’s rustic Adirondack siding that has become damaged over the summer. He’ll bring in our swim raft from its summer position out in the lake. 

Kevin will clean out the gutters and downspouts and check the roof for loose shingles – which is very appreciated by someone who avoids ladders. During a couple of especially brutal winters, Kevin has climbed a ladder past the three-foot icicles onto the snowy roof and shoveled it off to prevent ice dams from backing up under the eaves and into the attic. 

Basically, he’ll do anything we don’t want to do or can’t do. We handle taking down the window screens and much of the gardening, such as planting bulbs and pruning shrubs in late autumn. We have someone come and mow the leaves instead of raking or blowing them. We then mulch the leaves for compost or leave them in the yard to be absorbed. We clean the gardening tools – spades and shovels and pitchforks like a little oil on the metal parts over the winter – and put away the hoses. If we had a sprinkler system, we’d drain it. If we have leftover paint or stain or other liquids in the unheated garage as summer ends, we move them to the partially heated basement to keep them from freezing. We bring the batteries for cordless electric tools into the house.  

Sometimes Kevin’s winter prep includes bigger projects that we have been putting off, such as replacing six drafty 50-year-old windows. Some homeowners find those bigger projects by getting an efficiency inspection to see where and how they can invest in keeping their houses warmer for less money.

Kevin isn’t a chimney sweep, so we have someone else come in and do that every autumn in anticipation of the almost nightly fires we have when we’re at the house during the colder months. Kevin does have a firewood sideline, though, so we usually get him to deliver and stack a cord or two. It’s a good idea to make sure the furnace gets an annual maintenance call during the summer, and the generator or heat pump, too, if you’ve got them.  

You might always want to make seasonal adjustments to ceiling fans. They should blow down in summer to feel the breeze, and then reversed in winter to blanket the windows and exterior walls with warm air.

Maybe Kevin’s most valuable service is what he calls “winter watch.” Any day the thermometer dips below freezing, he’ll swing by and come into the house to look around and make sure everything is ok, and that there are no leaks or burst pipes, inside or out. 

When we first got the house, 14 years ago, the idea of a winter watch seemed totally unnecessary to me. What could go wrong? But we decided to try it. A few years ago, Kevin’s partner Bob stuck his head into our house one wintry day and sensed that something was wrong. The heat was off. The lights weren’t working. Bob went down into the basement, pulled open the fuse box and was blown back by a short burst of flame. He quickly turned off the outside power to the house – and probably prevented a fire. The utility company subsequently admitted that a work crew had made a mistake while repairing power lines out on the road; if Bob hadn’t checked on the house, our place probably would have burned to the ground. 

If we’re going to be away from our place for more than a day or two, we turn down the heat, usually setting the thermostat in the mid50s. Some of our neighbors have apps that let them use their phones to turn up the heat from the city a few hours before they arrive. Our house is not particularly smart, so we still wait until we walk in the door to turn the heat back up – unless we call Kevin the day before and ask him to turn the heat back up before we return. 

People who have true summer homes typically have a different set of tasks when they close up for the autumn, knowing that they won’t be back until spring. They still check the roof and the insulation, but they also turn off the gas and water to the entire house. The electricity, too. And they unplug all the appliances. Our friends with cabins in the Rockies clear out all the food from the pantry, not only to give the mice less reason to invade, but the bears, too. 

By the time all the winter prep is finished at our house, we’re more than ready to light the fire and plan the Thanksgiving menu and think of winter as less a season than a celebration.

We also remember another quote from another famous American.

“I love the scents of winter! For me, it’s all about the feeling you get when you smell pumpkin spice, cinnamon, nutmeg, gingerbread and spruce.” – Taylor Swift

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1 Comment

  1. Thank you, Tim, for another helpful article. Thanks to you we now have a guy; his name is Shaun and, among many other issues, he noticed that our AC/heater filter needed changing. For some reason, duh? Mike and I never thought about it. We really, really need “a guy”.
    He has helped us in many ways. Although we never get below freezing, thank God, we do get to about 114 degrees in the summer which presents another whole host of issues. Your suggestion of having “the guy” stop by every few days to check on things is one we will adopt for sure. Thanks again. Sue and Mike from Coronado and Borrego Springs, CA.
    PS – still haven’t found a “signature dish” but we’re working on it.

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