The Hudson Valley second-home seasonal calendar
Every one of these dates exists because somebody learned it the expensive way. This is the year as it actually happens to a house west of the Hudson — the version I run my own visits by.
Fall ramp-up
First gutter and leaf pass. Furnace service window opens — get it done before the first cold night, not after. If the house needs winterizing, this is when it gets scheduled.
Frost is now possible everywhere
The river towns may hold out another week or two, but treat mid-October as the frost trigger across the whole territory — the higher terrain in interior Sullivan and western Ulster can see its first freeze as early as October 7. Hose bibs and irrigation should be getting shut off and drained now.
Winterization complete
Second gutter pass done after peak leaf-drop. Exterior water off and drained. Heat set and verified at 55°F or better — the number your insurance policy quietly cares about. Higher-elevation houses should hit this bar by mid-October.
Sustained freeze is the norm
From here on, below-freezing is the default, not the exception. Any house that isn't winterized or actively heated is now carrying real burst-pipe risk every single night. Weekly checks should verify the heat is holding, not just set.
Nor'easter season
Peaks January–February. The risks stack: snow load, ice dams backing water under shingles, and power outages that take the heat down with them — which is how a storm turns into a freeze claim three days later. After every major storm, the house should get eyes on it within 24 hours.
The melt
Snowpack comes off the hills and the water table rises — this is sump-pump season. Post-melt gutter and drainage check, and a look at what winter did to the roof, driveway, and grading.
Spring opening — valley floor
Safe to de-winterize the river-corridor towns: water back on, exterior spigots reopened, AC serviced ahead of the season, screens in.
Spring opening — higher elevations
The hills frost later than the river. Interior Sullivan and western Ulster can catch a freeze into late May — opening those houses on the valley-floor schedule is how you get a cracked pipe in a house you just turned the water on in.
Peak rain
Statistically the wettest month of the year here. Moisture and humidity checks in basements, dehumidifiers running, grading and downspouts doing their jobs.
The flood window
Tropical-remnant season — and this region has the receipts: Irene in 2011, Sandy in 2012, and Ida in 2021, which put record flash flooding through parts of Orange County. A separate risk season from winter storms, with its own checklist: drainage clear, sump tested, downspouts extended, dead limbs off the trees.
One rule ties the whole calendar together: the hills run two to three weeks ahead of the river in fall, and two to three weeks behind in spring. If your house is up in the Catskill-adjacent terrain, shift every fall date earlier and every spring date later.
This calendar is what we run on
Hudson Ally works this schedule so you don't have to remember it — weekly walkthroughs, seasonal turnovers, storm checks within 24 hours, and a photo report after every visit. Orange, Sullivan & Ulster counties.
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