Your gutters catch the water. Your downspouts move it away from your home. If either one fails, the other doesn’t matter — and up here in the Poconos, both get hit hard every single season. Simon Says Roofing keeps the whole drainage system working across Monroe County, from the trough at the top to where the water exits at the bottom.
Most homeowners think about their gutters. Almost nobody thinks about their downspouts until something goes wrong. A clog, a disconnected joint, water dumping right next to your foundation — these problems start quietly and get expensive fast. Simon Says Roofing handles gutters and downspouts together, the way they’re supposed to be maintained.
The Pocono Mountains throw a lot at a drainage system — heavy leaf fall, brutal winters, ice, and storms that dump serious water in a short amount of time. Here’s what Simon Says Roofing deals with most often on homes across Stroudsburg and Monroe County:




We check everything — gutters, downspouts, hangers, joints, and where the water discharges at the bottom. The problem is usually somewhere most people aren't looking.
Clogs get flushed out, disconnected joints get re-sealed or replaced, and anything that's crushed or corroded gets swapped for new material that fits.
We run water through the system top to bottom, confirm everything is draining where it needs to go, and make sure nothing is backing up or leaking before we leave.
Whether it’s one bad downspout or the whole system needs attention, our crew handles it all for homes and businesses throughout Stroudsburg, East Stroudsburg, Mount Pocono, and the rest of the Pocono region.
Leaking joints, sagging sections, hangers pulling loose — we fix what can be fixed and replace what can't. If the gutters have had it, we put new seamless gutters up that have fewer joints and hold up better in this climate.
Crushed, cracked, disconnected, or just falling apart — downspouts take a beating every winter up here and most homeowners don't notice until water is running down the wrong side of the house. We repair or replace them and make sure they're secured properly.
A clogged downspout backs up the entire gutter system. We flush them out completely, check for anything that's causing the blockage to keep happening, and make sure water is moving all the way through from top to bottom.
Gutter guards cut down on the amount of leaves and debris that get into the system in the first place — which matters a lot in the Poconos where the tree cover drops a serious amount of material every fall. We install guards that fit your gutter type and work with the way water flows on your roof.
Where the water exits at the bottom of the downspout is just as important as everything above it. Extensions and diverters move water a safe distance away from your foundation — something that every home in this region needs. We install, repair, and adjust them based on your yard's grade and layout.
Storm just came through and water is pouring out of a spot it shouldn't be? Simon Says Roofing responds to emergency drainage repairs across Monroe County fast — before the next round of rain turns a bad joint into a foundation problem.
A lot of contractors will look at your gutters and ignore your downspouts — or the other way around. Simon Says Roofing checks and services the entire drainage system as one unit, because that's how it actually works. We're based in Stroudsburg, we know what this climate does to gutters and downspouts every year, and we fix it the right way so you're not calling us back next month for the same thing. Free estimate, no pressure.
Don’t wait for small roofing issues to turn into costly problems. Whether you need a repair, a full replacement, or a professional inspection, Simon Schedule your free estimate with Simon Says Roofing today. Quality work, honest service, and peace of mind start here.
At least twice a year — once in late spring after everything has thawed out, and again in late fall after the leaves have come down. The tree coverage in this part of the mountains drops a lot of debris, and if you skip a season it piles up fast. Downspouts especially need to be checked both times, not just the gutters.
The water has to go somewhere — and if it can’t go down the downspout, it backs up into the gutter and spills over the edge. That water runs down your siding, pools against your foundation, and starts working its way into the ground right where you don’t want it. It’s one of the easiest problems to fix and one of the most expensive to ignore.
Almost certainly yes. The ground around most homes in the Poconos slopes in ways that can direct water back toward the foundation if the downspout just drops it right at the base of the house. Extensions move the discharge point several feet out — and that small difference is a big deal when it comes to keeping water out of your basement or crawl space.
If the damage is limited to a few spots — a bad joint here, a crushed section there — repair makes sense. But if the gutters are sagging across long runs, the hangers are all failing, and the downspouts have been patched multiple times already, new seamless gutters and fresh downspouts are the better investment. We’ll look at what you’ve got and give you a straight answer.
Simon Says Roofing services the full drainage system — gutters, downspouts, guards, and extensions — for homes across the Pocono Mountains. Call (570) 202-6631 or reach out online for a free estimate today.
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925 N 9th Street
Stroudsburg, PA 18360