Before Winter: The Fall Maintenance Checklist Greater Boston Homeowners Actually Need

This is the walkthrough we run through with our Home Care members twice a year. Here's the fall version.

Roof edges, gutters, and downspouts

This is the ice-dam prevention round, and it matters more here than almost anywhere else in the country.

• Clean gutters and downspouts after the leaves are down — clogged gutters hold water at the roof edge, exactly where ice dams start.
• Confirm downspouts discharge well away from the foundation, with extensions intact.
• From the ground, look for lifted or missing shingles, damaged flashing at chimneys and valleys, and any sagging at the eaves.
• Check that attic ventilation isn't blocked. A warm attic melts snow unevenly; the meltwater refreezes at the cold eave and works under the shingles.

Heating system, before the first cold snap

• Schedule the annual service for your furnace or boiler now, not during the first freeze when every tech in the Boston area is booked out. Burners get cleaned, filters replaced, safety controls tested.
• Bleed radiators and check for cold spots if you have hydronic heat.
• Test the thermostat, and replace backup batteries if it has them.
• If you heat with oil, confirm your tank gauge works and your fill pipe and vent are clear.
• Know where your heating system's emergency shutoff switch is. (It's usually the red switch plate at the top of the basement stairs — make sure everyone in the house knows it.)

Chimney and fireplace

• Have the chimney inspected and swept annually if you burn wood. Creosote buildup is a fire risk, and a sweep will also spot cracked flue tiles and failing mortar at the crown.
• Check the damper opens, closes, and seals. A damper stuck open is a heated-room leak all winter.
• Look at the chimney cap — a missing cap lets water, animals, and debris straight in.

Water: shut it down outside, protect it inside

• Disconnect garden hoses. A hose left attached can freeze back into the pipe and split it inside the wall — the leak often isn't discovered until spring.
• Shut off interior valves to exterior hose bibs and open the outside faucet to drain. Frost-proof faucets still need the hose off.
• Drain and winterize irrigation systems before the ground freezes.
• Inside, find any pipes running through unheated spaces — garages, crawl spaces, exterior walls — and note which ones need watching during deep cold snaps.

Caulking, paint, and the exterior shell

• Walk the house and look at caulk joints around windows, doors, and trim. Failed caulk is the single most common entry point for water we find, and water in a wall assembly does its damage quietly.
• Check for peeling or blistered paint, especially on sills and the bottoms of trim boards. Bare wood going into a New England winter will not come out the same.
• Look at grade around the foundation — soil and mulch should slope away, and window wells should be clear.

Weatherstripping, windows, and attic air leaks

Heating bills aside, air leakage at the top of the house feeds ice dams.

• Check weatherstripping on exterior doors; if you can see daylight around a closed door, it's leaking.
• Confirm storm windows are down and latches set, or that combination windows are sealed.
• In the attic, look for obvious gaps around the hatch, recessed lights, and plumbing vents. Sealing the attic hatch alone is a cheap, noticeable fix.
• If your insulation is thin or uneven, fall is the time to address it — and a Mass Save home energy assessment can identify where your house is losing heat before you spend on the wrong fix.

Basement, sump, and drainage

• Test the sump pump: pour in water until the float triggers and confirm it discharges. If you have a battery backup, check its charge — the pump you need most is the one running during a storm-related outage.
• Look for new water staining on foundation walls and note it now, so spring meltwater problems can be compared against a fall baseline.
• Clear leaves and debris from exterior drains and stairwell drains.

Generator and safety checks

• If you have a standby generator, run it under load briefly, check the oil, and confirm the transfer switch cycles properly. Generators fail in the outage they were bought for when they've sat untested.
• Test every smoke and carbon monoxide detector and replace batteries. Massachusetts requires CO detectors on every level with a bedroom or a fuel-burning appliance — test them all, and replace any detector past its printed expiration date (most are 10 years for smoke, 5–7 for CO).
• Walk decks, porches, and exterior stairs: loose railings and rotted treads are a different problem under snow and ice. Check exterior lighting on walkways, too.

How Hawthorn Home Care handles this

Our Home Care members don't keep this list on the fridge — we walk it for them. Twice a year we go through the house and property, document what we find with photos and video, and turn it into an itemized estimate. Members approve the items they want done, item by item, before any work starts — gutter cleaning, HVAC tune-ups, duct and vent cleaning, and the small repairs that keep a fall finding from becoming a January emergency. Work beyond the membership is handled time-and-materials plus a coordination fee, with the plan and budget visible to the member as it goes.

However you handle it — your own ladder, your own list, or ours — the point is the same: an hour of looking in October is cheaper than a ceiling in February. If you'd like to talk about how the walkthrough cadence works, or you have a question about something you've spotted on your own house, ask us — a question is always free.