Fall is a good time to prepare your home for winter weather. Southern Maryland homes can experience heavy rain, strong winds, hail, freezing temperatures, and freeze-thaw cycles. Small exterior problems can become larger problems when they are not addressed before winter.

Use this checklist to review your roof and exterior. Complete simple tasks safely from the ground. Contact a professional for roof areas, ladders, or storm damage that require specialized inspection.
1. Clean the gutters before leaves peak
Gutters should be cleaned before they become full of leaves and other debris. If trees are close to your home, plan for a second cleaning after most leaves have fallen.
Clogged gutters can cause water to overflow onto:
- Roof edges
- Fascia boards
- Soffits
- Siding
- Windows and doors
- Foundation walls
- Landscaping
Water that remains against these areas can lead to rot, staining, leaks, and other damage. During freezing weather, clogged gutters can also contribute to ice buildup and backed-up water.
Gutter checklist
- Remove leaves, twigs, and roof debris.
- Flush gutters with a hose.
- Confirm that water flows through every downspout.
- Check for sagging or separated gutter sections.
- Look for loose hangers and fasteners.
- Inspect seams for leaks.
- Make sure downspouts direct water away from the foundation.
- Check the fascia behind the gutters for staining or soft wood.
Capital Roofing and Exteriors provides gutter services for homeowners and businesses. Services include gutter cleaning, repairs, and replacement.

2. Check for hidden summer storm damage
Summer storms can cause roof and exterior damage that is not easy to see from the ground. Hail may leave small impact marks. Wind may lift or crease shingles without removing them completely. Damage may become more serious during the next period of heavy rain or strong wind.
Inspect your home after summer hail, wind, or severe thunderstorms. Look for changes that were not present before the storm.
Common signs of hidden storm damage
- Missing or shifted shingles
- Lifted or creased shingle tabs
- Cracked or broken roofing materials
- Areas with unusual granule loss
- Dented metal flashing or vents
- Loose siding panels
- Cracked siding
- Damaged trim
- Broken window seals
- Water stains on ceilings or walls
- Damp insulation in the attic
- Debris or tree limbs on the roof
Do not walk on the roof to inspect it yourself. Roofing surfaces can be slippery and unstable. Use binoculars from the ground or schedule a professional inspection.
Capital Roofing and Exteriors offers a free roof inspection and storm damage assessment. The company can also assist with the insurance claim process and meet with the insurance adjuster when appropriate. A detailed inspection can help identify damage before it develops into a larger repair.
For additional information, review how wind can damage your home.
3. Inspect shingles and roof surfaces
Shingles protect the roof deck and the interior of your home. Fall is a suitable time to check their condition before temperatures drop.
From the ground, look for:
- Curling or buckling shingles
- Missing shingles
- Dark or damaged areas
- Excessive moss or algae
- Exposed roof surfaces
- Debris in valleys
- Sagging areas along the roofline
Shingles naturally age from exposure to sun, rain, wind, and temperature changes. Older shingles may become brittle and lose granules. A roof with widespread deterioration may need more than a small repair.
Some problems can be corrected with targeted roof repairs. Others may require replacement. A professional inspection can help determine the correct option.
Visit the roof repair service page for information about missing shingles, minor leaks, damaged flashing, and other common repairs. Capital Roofing and Exteriors also provides roofing services for repairs, replacements, inspections, and storm damage restoration.
4. Review flashing and roof penetrations
Flashing helps direct water away from vulnerable roof areas. These areas include:
- Chimneys
- Valleys
- Skylights
- Plumbing vents
- Roof-to-wall connections
- Dormers
- Porches and additions
Check visible flashing from the ground. Look for pieces that appear loose, bent, rusted, or separated. Sealant around roof penetrations can also deteriorate over time.
Flashing problems can allow water to enter without causing an immediate visible leak. Check the attic for dark marks, stains, wet insulation, or a musty odor. If you find evidence of moisture, schedule an inspection promptly.
5. Seal windows and exterior doors
Windows and doors are important parts of the exterior weather barrier. Gaps or damaged seals can allow drafts and moisture to enter the home.
Check the following areas:
- Exterior caulking around frames
- Weatherstripping around doors
- Cracked or broken glass
- Loose trim
- Gaps around window frames
- Water stains below windows
- Soft or swollen wood
- Fogging between glass panes
Replace damaged weatherstripping where needed. Recaulk small exterior gaps while temperatures are still suitable for the product being used. Larger gaps, damaged frames, or water intrusion may require professional service.
Capital Roofing and Exteriors provides window and door services that include window installation, replacement, and sealing.

6. Check siding, trim, and exterior walls
Siding protects the wall system from rain, wind, and moisture. Summer storms can crack, loosen, or displace siding. Small openings can allow water behind the exterior surface.
Walk around the home and inspect:
- Cracked or broken siding
- Loose panels
- Buckled or warped sections
- Open seams
- Damaged corner posts
- Missing trim
- Peeling paint
- Staining below roof edges
- Soft areas around windows and doors
Do not cover damaged siding without checking for moisture behind it. Water can remain hidden and damage wall materials, insulation, or interior finishes.
Capital Roofing and Exteriors offers siding installation and repair for residential and commercial properties.
7. Trim overhanging branches
Tree branches that touch or overhang the roof can create several problems. They may scrape shingles, drop debris into gutters, and damage the roof during high winds. Dead branches can also fall during storms.
Before winter:
- Remove dead or damaged branches.
- Trim branches that contact the roof.
- Keep large limbs away from roof surfaces when possible.
- Remove branches that block gutters.
- Hire a qualified tree professional for large or unstable limbs.
Do not attempt to remove branches near power lines. Contact the appropriate utility or tree service provider instead.
8. Check drainage around the foundation
Gutters and downspouts should move water away from the home. Check the soil around the foundation after a heavy rain.
Look for:
- Standing water
- Soil erosion
- Water marks on foundation walls
- Downspouts discharging too close to the home
- Cracks near the foundation
- Gaps where siding meets the foundation
Adjust downspout extensions if water is released near the foundation. Correct drainage can reduce moisture problems in basements, crawl spaces, and lower-level walls.
9. Schedule a professional roof inspection
A professional fall roof inspection is recommended if:
- Your home had summer hail or wind exposure.
- You see missing, lifted, or damaged shingles.
- The roof is older.
- You notice stains or leaks inside.
- Gutters are pulling away from the fascia.
- You plan to sell or renovate the property.
- You have not had a roof inspection recently.
A qualified inspector can review shingles, flashing, roof penetrations, gutters, ventilation, and signs of hidden moisture. Capital Roofing and Exteriors is HAAG Certified and provides free roof inspections for homeowners and businesses.
The company also offers bi-monthly and annual roof maintenance to help identify problems early and support long-term roof performance.

10. Complete winter preparation tasks
After reviewing the roof and exterior, complete other basic winter tasks:
- Drain exterior faucets and hoses.
- Insulate exposed pipes in unheated areas.
- Service the heating system.
- Replace HVAC filters.
- Check attic insulation for gaps or moisture.
- Test smoke and carbon monoxide detectors.
- Check exterior lighting.
- Store outdoor equipment.
- Prepare snow and ice removal supplies.
- Inspect the chimney if it is used.
These tasks help prepare the complete property for colder weather.
Schedule a fall inspection in Southern Maryland
Fall maintenance can help reduce the risk of leaks, water damage, and emergency repairs during winter. Capital Roofing and Exteriors provides roofing, gutters, siding, windows, storm damage assessments, and maintenance services.
We proudly serve homeowners and businesses across Southern Maryland, Virginia, and Pennsylvania. See our full list of service areas.
To request a free inspection, visit the contact page, call 443-977-1494, or email info@capitalroofingmd.com.
Capital Roofing and Exteriors 25 Valley Dr. Huntingtown, Maryland 20639 Hours: 9 a.m.–6 p.m. 24/7 emergency services available
Related Resources
- How Your Gutters Are Secretly Shortening Your Roof’s Lifespan — and What to Do About It
- Winter’s Hidden Threat: How Ice Damage Can Ruin Your Roof
- Roof Maintenance Checklist for Homeowners: Monthly & Annual Tips
- Power Washing Services
- Holiday Light Installation
- More Roofing Tips on Our Blog
- Top 10 Siding Questions Answered: A Guide for Southern Maryland Homeowners
- Top 10 Gutter Questions Answered: A Guide for Southern Maryland Homeowners
- Top 10 Window Replacement Questions Answered: A Guide for Southern Maryland Homeowners

