Jimmy Davidson founded Silver Loon Roofing in Crosby, Minnesota, in 2026. Before that he spent more than 30 years building custom homes in the Crested Butte area of the Colorado Rockies, mostly framing, interior and exterior trim, and roofing, with plumbing, electrical, painting and drywall work along the way. He lives in Crosby with his four kids, scopes every estimate himself and checks every job.
The best time to fix a roof in lake country is the four weeks before the ground freezes. Small problems you find in October cost little. The same problems found in February, under two feet of snow, cost a lot more.
Here are eight checks we run on every fall visit. Most of the first six you can do from the ground, with a pair of binoculars and a flashlight.
Check the outside first
1. Clean the gutters and downspouts. Wait until most of the leaves are down, then clear them out. A full gutter holds water at the eave. In winter that water freezes and backs up under the shingles. Make sure each downspout drains away from the foundation.
2. Look at the shingles. Scan for curled edges, missing pieces, and bare spots where the granules wore off. Look for dark streaks of grit in the gutters, too. A few lost shingles after a wind storm is normal. Fix them before snow lands on them.
3. Check the flashing. Flashing is the metal at the chimney, the valleys, the walls, and around pipes. Look for gaps, rust, or old sealant that cracked and pulled away. Chimneys and skylights leak more often than open roof areas.
4. Look at the vents and pipe boots. The rubber collar around a plumbing vent wears out and splits with age. A split collar lets melt water run right down the pipe. Bath fan and range hood caps should have a flap that closes.
5. Trim the trees. Pine and oak limbs that touch the roof scrape off granules and drop needles into valleys. A heavy wet snow can also snap a dead limb onto the roof. Cut back anything within a few feet. Hire a tree service for big limbs.
6. Check the eaves and fascia. Look for peeling paint, soft wood, or gaps where birds and squirrels could get in. An open gap at the eave is a way in for animals, and for wet air.
Then check the attic
7. Go up with a flashlight. Look at the underside of the roof deck. Dark stains, wet insulation, or frost on the nails mean air is leaking from the house into the attic. Look at the attic hatch, too. If it is not sealed and insulated, warm air pours through it all winter.
This matters because of ice dams. Heat from the living space warms the roof, melts the snow, and the water refreezes at the cold edge. The University of Minnesota Extension says the first fix is to make the ceiling airtight so warm, moist air cannot reach the attic. Add insulation after that. We cover the full story in our posts on ice dam causes and attic insulation and ventilation.
8. Know what is under your shingles. Minnesota city building handouts, such as this one from Hastings, say an ice and water barrier goes from the eave up to a point 24 inches inside the exterior wall line. If your roof is older, ask whoever looks at it whether that barrier is there. Without it, one ice dam can put water into your wall.
If you leave the cabin for winter
Cabin owners have a harder job, because nobody is watching the roof. Before you lock up:
- Clear the gutters and walk the roof line one last time.
- Cut back any limb that hangs over the roof.
- Seal the attic hatch and any open gaps so warm air does not leak into the attic.
- Pick someone to look at the roof after the big storms. A foot or more of snow sitting on one slope is a good time to call. The Extension notes that removing snow from the roof takes away one of the things an ice dam needs.
We run winter roof maintenance routes for lake homes. We clear the roof, check the eaves, and send photos after each visit, so you do not have to drive up to see it.
What to do with what you find
Minor items, like a clogged gutter or a bad pipe boot, are quick fixes. Rotted deck boards, wet insulation, or shingles that are worn across a whole slope are not. If most of the roof is near the end of its life, plan the replacement for spring. Do not wait for it to fail in January. A typical replacement runs $9,000 to $22,000 installed, depending on size, pitch, and material.
Bottom line
Spend an hour in October on the gutters, shingles, flashing, vents, trees, and attic. Fix the small things now. If something looks wrong and you are not sure, have it checked before the first real snow.
Want a second set of eyes? We will look at your roof and attic for free. Book a free inspection and we will come out before freeze-up.
Jimmy Davidson founded Silver Loon Roofing in Crosby, Minnesota, in 2026. Before that he spent more than 30 years building custom homes in the Crested Butte area of the Colorado Rockies, mostly framing, interior and exterior trim, and roofing, with plumbing, electrical, painting and drywall work along the way. He lives in Crosby with his four kids, scopes every estimate himself and checks every job.
More from Jimmy →