Fairfield County Winters: Protecting Your Roof and Gutters from Wind, Ice, and Snow

If you’ve lived in Fairfield County long enough, you know that winter here doesn’t hold back. Being a little farther north than our neighbors in Westchester, we see even colder temperatures, heavier snowfalls, and more frequent ice storms.

Once you get past I-684 and into the foothills of the Berkshire Mountains, winter really starts to feel like… well, winter.

Homes along the Long Island Sound face a different kind of challenge—powerful Nor’easters that bring howling coastal winds, freezing rain, and heavy, wet snow. And the further north you go, deeper into New England, the more unpredictable the storms become. One day it’s a dusting of snow; the next, it’s a foot of ice-packed powder with brutal winds and subzero wind chills.

No matter where you live in Fairfield County, winter is relentless—and your roof and gutters take the brunt of it, but a little attention now can help you avoid big headaches (and expensive repairs) later.

No Matter What Mother Nature Throws at Us, We’ve Got You Covered

As our founder, George Curi, puts it:

“We know winter in Fairfield County isn’t for the faint of heart. The storms hit hard, the snow piles up, and ice gets into every little crack. That’s why we take your roof and gutter system seriously—because your home is your first line of defense, and we’re here to help keep it that way.”

We’ve been working on homes across Fairfield County for years. We live here, too, and we’ve seen firsthand what wind, ice, and snow can do to a roof. Here are five common winter problems we see—and what you can do to prevent them.

Fairfield County Winters

1. Wind-Damaged Flashing: A Small Issue That Leads to Big Leaks

Protecting Your Roof and Gutter

Roof flashing—the thin metal that seals gaps around chimneys, vents, and skylights—is one of the first things to go in a strong storm. With Fairfield County’s mix of coastal storms, valley winds, and heavy snowfall, flashing can get bent, loosened, or even ripped off entirely. Once that happens, water finds its way in, and before you know it, you’ve got leaks inside your home.

Need Flashing Repair? We can help: Chimney Flashing Repair in Fairfield, CT

How to Spot Flashing Damage:
  • Water stains on ceilings or walls, especially near chimneys and skylights.
  • Bent, cracked, or missing metal flashing around roof edges.
  • Rust or corrosion, which weakens the seal over time.
What You Can Do:
  • After a storm, check for visible flashing damage or leaks inside.
  • If you see rust or gaps in flashing, get it repaired before water gets in.
  • A quick repair now can save you thousands in water damage down the road.

2. Skylights and Snow Load: A Risky Combination

Skylights are great for bringing in natural light, but in a Fairfield winter, they can be a weak point in your roof. Heavy snow sitting on top, combined with freezing and thawing cycles, puts pressure on the glass and seals. Coastal homes along the Sound deal with additional wear from wind-driven rain and salty air, while homes further inland see heavier, longer-lasting snow that can lead to cracking and leaks.

Need Skylight Repair or Installation? Learn more here: Skylight Installation & Repair in Fairfield County, CT

Skylight and Snow Load
Signs of Skylight Trouble:
  • Water pooling around the inside of the skylight.
  • Condensation trapped between glass panes.
  • Cracks or stress fractures in the skylight glass.
How to Prevent Skylight Damage:
  • Use a roof rake to remove heavy snow from around skylights (never climb up yourself!).
  • Check for leaks or drafts along the skylight frame after a storm.
  • If you see condensation inside the glass, the seal may be failing—get it looked at before it leads to water damage.

3. Ice Dams: The Hidden Roof Killer

Gutter Repair Ice Dams

“If you’ve ever seen huge icicles hanging from your gutters, you might think they look pretty—but they’re actually a warning sign.” —George Curi

Ice dams are one of the biggest winter problems we see in Fairfield County. They form when heat escapes from your attic, melting the snow on your roof. That melted snow refreezes at the edges, creating a thick ridge of ice. As the ice dam grows, water backs up behind it, seeping under shingles and into your home.

Need Roof Repairs? We can help: Roof Repair in Fairfield County, CT

How to Prevent Ice Dams:

  • Keep your attic well-insulated to prevent heat from escaping.
  • Make sure your gutters are clear so melting snow can drain properly.
  • If an ice dam forms, don’t try to chip it away—that can damage your roof. Call a professional instead.
Wind and Snow Damage to Shingles

4. Wind and Snow Damage to Shingles: A Common, Costly Issue

Heavy snow and high winds put a lot of stress on shingles, especially on older roofs. In the foothills of the Berkshires, where winter storms hit hardest, we often see shingles torn off, cracked, or worn down. If your roof is more than 15 years old, you’ll want to keep a close eye on its condition this winter.

Need Fascia or Soffit Repair? Learn more: Soffit & Fascia Repair in Fairfield, CT

5. Gutter Overload: Ice, Snow, and the Weight of Winter

Your gutters work hard all winter, directing melting snow and rain away from your home. But when they’re clogged or damaged, water has nowhere to go—leading to ice buildup, sagging, and even complete gutter failure. The result? Water pooling around your foundation or leaking into your roof.

Need Gutter Repairs? We specialize in it: Gutter Repair in Fairfield, CT

Gutter Overload In Winter
How to Keep Your Gutters Working All Winter:
  • Clean them out before the first big snowfall.
  • Install gutter guards to keep out debris and reduce ice buildup.
  • If your gutters are sagging or pulling away, get them fixed before they fail completely.
We’re Here for You—No Matter How Tough the Winter Gets

Fairfield County winters can be rough, but we’re here to make sure your home is ready for whatever Mother Nature throws at it.

“We live here, too—we know how brutal these winters can be. That’s why we take every repair seriously. Whether it’s fixing a leak, clearing an ice dam, or making sure your gutters can handle the weight of the snow, we’ve got you covered.” —George Curi

Stay safe, stay warm, and remember: a little prevention goes a long way in keeping your home protected. If you’re worried about damage after a storm, let us take a look—we’re always happy to help.

Fairfield County Homeowners Trust George’s Seamless Gutters

Whether you’re preparing your roof for winter or dealing with an existing issue, our team has the expertise to keep your home safe and dry. Contact us today to schedule a winter inspection.

George’s Seamless Gutters Repair

Our Customers

  • “I hired George this past spring - after suffering with damage caused by our previous winters ice dams. He came right out after I called him, assessed my gutter damage and helped me select a gutter system right for my home. I recommend him to all my family and friends! Great job! Thanks George!”

    Bailey W.,Fairfield CT
  • “Quite possibly the best service I've ever received from a home improvement company...called them at noon, described the problem (small terrace with pooling water from roof runoff), and by 3pm, they had come out, diagnosed the problem, and installed the gutter. Fantastic service!”

    John D.,Scarsdale, NY
  • “They responded immediately. Did the work the same day I signed the contract, because as a recent widow, they did not want to me to worry. Cleaned up everything. Efficient and professional. Gutters look and work great.”

    Naomi B.,Rye Brook, NY
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