Preparing Your Boston Property for Winter: A Fall Checklist
Published September 2026
Boston’s snow season runs December through March. Every winter since 2022 we have cleared more properties than the winter before, and the properties that go smoothly on a snow day are the ones that were ready in October. This is the October list. Seven things, in the order to do them, each one something we have watched go wrong on a snow day. It applies to Boston and the surrounding towns: Back Bay, Charlestown, Fenway, Cambridge, South Boston, East Boston, Roslindale, Brookline, North End, Jamaica Plain, Allston, Dorchester, Hyde Park, Roxbury, Mattapan, Somerville, Arlington, Everett, Malden, Medford, Newton, Quincy, Revere, and Watertown.

1. Sign up before the first storm, and pick your trigger
Our route is built in the fall and worked in the same order all winter. Last winter it held 321 properties, and the first full-route day came on December 27, when our crews cleared 267 of them in one day. A property that signs up after that date goes onto a route that is already running, and on a big storm the new addresses are the ones at the end of the day.
Signing up means choosing a trigger: how much snow has to fall before we come out. About half of our customers set it at 2 inches, and for most properties that is what we recommend. Below that line the risk is ice, not snow, and ice is handled with salt on the nights when almost nothing falls but the temperature drops. Last winter our crews went out on 10 separate days with zero measured accumulation, to roughly 550 properties, for salt alone.
If your property is unusually exposed, a north-facing walkway that never sees sun, a steep entry, an elderly tenant, tell us when you sign up and we will talk about a lower trigger or a standing salt arrangement.
2. Decide about salt now, not during the storm
Three out of every four visits we make end with salt on the walkway. Salt is what keeps a cleared sidewalk from turning into a sheet of ice by morning, and it is the reason a property can be cleared at 1 AM and still be safe at 7 AM.
Not every property wants it. Fifty-four of our customers tell us no salt, and they have good reasons: a dog that walks the sidewalk, a garden bed right at the edge, brick or bluestone that pits, concrete that spalls. If that is you, tell us in the fall so it is written on your property before the first visit. A handful of customers supply their own. If you are one of them, buy it in October, when it is on the shelf and cheap, and show us where it is kept. By February the good stuff is expensive and sometimes gone.
3. Clear the path to the trash bins and the back entrance
The two things under snow before anyone thinks of them. “Trash bin path” is written on more than 200 of our job notes and “back entrance” on nearly 1,400, because the crew clears what it can reach and the bins are usually down a side passage behind a grill, two bikes and a bag of mulch left over from spring.
In the fall, move the bins to a spot the crew can reach from the front, or at least clear the passage of everything that is not the bins.

4. Fix the gate latch, and tell us how to get in
Nearly 250 of our job notes mention a gate. A gate that sticks in October is frozen shut in January, and a padlocked gate on a storm day means the back steps stay under snow until someone is home. Oil the latch, fix the sag, and if the gate locks, give us the code or leave it open on storm days.
5. Decide where the snow goes
On a small city lot there is nowhere to put it, and every choice has a cost. Piled against the house it melts into the foundation. Piled on the neighbor’s car it starts a feud. Pushed into the street it is against the rules in every town we work in. Decide now, while you can see the yard, and tell us:
- Which side of the walkway the pile goes on, and where the gate needs room to swing.
- Whether you need a car space shoveled out. More than 300 of our job notes ask for one, and it changes the time on the job.
- If you are on a corner, you have two sidewalks, and the city fines each one.

6. Fix the steps and railings while it is warm
Most of the falls we hear about are not on the sidewalk. They are on the front steps, on a tread that was already soft in September, holding a railing that was already loose. A rotted stair or a wobbly railing cannot be fixed in January, and a shovel finds every weak board. Walk your steps now, lean on every railing, and get anything that moves repaired before the first freeze. Our handyman crew does this work all fall: Greater Boston Handyman Services


7. Leaves and gutters last
The leaves you did not rake are the ice sheet on your walkway in December. They mat down under the first snow, hold water, and freeze into a layer that no shovel gets under. A clogged gutter does the same thing from above, dripping onto the steps and freezing in a stripe exactly where people put their feet. A fall cleanup in November is the last item on the list because it is the last thing that has to happen, not the least important. Our landscaping crew does more than 300 cleanups a year: Greater Boston Landscaping Services


The list
- Sign up before the first storm and pick your trigger. We recommend 2 inches.
- Decide about salt. Yes, no, or your own bag, and where it is kept.
- Clear the path to the bins and the back entrance.
- Fix the gate latch and tell us the code.
- Decide where the snow goes, and whether you need a car space.
- Fix the steps and railings while it is warm.
- Rake the leaves and clean the gutters in November.
Ready for winter?
We clear snow and ice across Boston and the surrounding towns: Cambridge, Somerville, Brookline, Medford, Quincy, Arlington, Watertown, and more. Every visit is documented with before and after photos, we work through the night so your sidewalk is clear before the deadline, and if you get fined for snow we were responsible for, we pay it. Request a free quote on our website or give us a call: