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TRUSTED BY TRAIL, OR HOMEOWNERS

  • Average homeowner rating star icon5
    Average homeowner rating
  • Verified reviews icon24
    Verified painting services reviews

Top-Rated Painters in Trail - Updated Nov 2026

Avatar for The Valley Painting Pros
The Valley Painting Pros
5.0(
21
)
Exterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: LargeInterior Home or Surfaces - Paint or Stain+7 more

Serving Trail, OR and surrounding areas

Approved

Super Service Award Winner

Free estimates

Warranties offered

Credit card accepted

"I have a cabin that had an old exterior stain product on it that was very susceptible to mold. The house exterior aged very poorly and was covered in a black mold. I hired valley painting pros in southern oregon to take care of it and they handled it perfectly. They safely stripped the mold and old stain off the house while keeping the wood in great clear shape. I love the stain color choice they picked and the product is very resistant to bugs and mold. Throughout the process they were very timely and professional. I would hire them again if I need more exterior restoration or staining work done."
Painting - Interior Project
Painting - Exterior Project
Painting - Exterior Project
Interior Painting Project
Painting - Exterior Project

+305

Response time6 hrs
Response rate100%
Recommended by36%of homeowners
Richard Shier Painting
4.7(
70
)
Exterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: LargeInterior Home or Surfaces - Paint or Stain+7 more

Serving Trail, OR and surrounding areas

Approved

In business since 1994

Free estimates

Offers commercial services

"I hired Richard Shier a couple months ago to paint the exterior of my home. I really appreciate the responsive and professional job that he did. The prepping that was done made such an improvement on my home. His work was beautiful and my home looks great. He quoted a price that was very reasonable. I would recommend him to anyone that wants their home painted,"
Before & After
Custom Ceiling
Additional Photos
Additional Photos
Response time9 hrs
Response rate100%
Recommended by98%of homeowners
Avatar for The Oregon Painting Company
The Oregon Painting Company
5.0(
5
)
Exterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: LargeInterior Home or Surfaces - Paint or Stain+7 more

Serving Trail, OR and surrounding areas

Approved

Free estimates

Warranties offered

Offers commercial services

"The Oregon Painting Company is one of the best companies I’ve ever had work on my house. Brandon was professional, on time, and very knowledgeable; it’s obvious he’s spent years honing his craft. Two of his crew members (Danielle and Katie) were so sweet and stayed extra hours to help finish the job. I’d hire Brandon and his team any time for any painting work, both interior and exterior. When I didn’t know that you had to scrape, sand, AND prime each side that had peeling paint, Brandon actually peeled off a paint chip and showed me in real time how he would do the prep work. Such an artisan, and a gentleman!!!! Try out the Oregon Painting Company today. 9.95/10, would work with again!"
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+7

Response time11 hrs
Response rate100%
2 neighbors recently requested a quote
TYREE MATTHEW FRESHNER
5.0(
5
)
Interior Painting or Staining: 1 - 2 RoomsInterior Painting or Staining: 5 + RoomsInterior Painting or Staining: 3 - 4 Rooms+1 more

Serving Trail, OR and surrounding areas

Approved

In business since 2022

Free estimates

Credit card accepted

"We hired Tyfresh Painting to do the exterior, trim, and front door on our house. The owner was super friendly and very knowledgeable, and got to work right away. He was incredibly fast and everything turned out looking way better than we could have expected. We highly recommend Tyfresh Painting!"
14 neighbors recently requested a quote
Recommended by100%of homeowners
Avatar for Pacific Builders Tim Hogue
Pacific Builders Tim Hogue
3.7(
35
)
Exterior Home or Structure - Paint or StainInterior Painting or Staining: 1 - 2 RoomsInterior Painting or Staining: 3 - 4 Rooms+2 more

Serving Trail, OR and surrounding areas

Approved

In business since 1992

Free estimates

Emergency services offered

"They did a power wash and painted my house. They fixed an electric gate that had collapsed. They fixed a water feature on my deck. They replaced a board on my deck. They fixed a stopped up sink. They were absolutely, off-the-chart fabulous!”"
Coustom base board
Dewitt's project
Dewitt's project
Dewitt's project
stone fire place

+42

Response time7 hrs
Response rate85%
1 neighbors recently requested a quote
Avatar for Brotherhood Painting
Brotherhood Painting
5.0(
22
)
Exterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: LargeInterior Home or Surfaces - Paint or Stain+7 more

Serving Trail, OR and surrounding areas

In business since 2003

Free estimates

Credit card accepted

"Choose Brotherhood Painting to paint the exterior of our home and sure glad we did. From Matt’s professional appraisal to the prep and paint crew attention to detail, couldn’t have asked for a better job. Would highly recommend Brotherhood Painting for all your painting needs. Thank you all of so much, our home looks so beautiful."
Recommended by100%of homeowners
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Painting FAQs, answered by experts

Yes, you can waterproof any wood that has not already been treated. A good way to test this is to splash some water on it. If the water starts to bead up, the wood is treated and most likely doesn’t need another coating.

Yes, you can paint a chain-link fence, but you don’t want to use spray paint. With the spray method, you’ll be losing a majority of your product to the air, given the size of the gaps in chain-link fences. Instead, use a paintbrush for your fence posts and a paint roller for the wire.

A dry lawn is easier to edge than a wet one. When your ground is wet, your blades will likely clump together, making a seemingly even cut while wet, but an uneven disaster when dried. Also, a wet lawn can impact your blade's performance and cause mud to kick up, resulting in a messy finish.

Most gutter painting pros also specialize in complete home exterior painting. You may save by making your gutter painting part of the cost to paint the exterior of a house in its entirety. Many people have all parts of their home exterior painted simultaneously to keep everything looking equally fresh. Consider having walls, trim, porches, shutters, and doors painted as well.

If your cedar fence is new, don’t delay. Unlike treated pine, you don’t need to wait months for the wood to dry out for it to accept stain. With cedar, the sooner, the better. Seal cedar within two weeks of installation to prevent the sun from fading its red color.

The Trail, OR homeowners’ guide to painting services

From average costs to expert advice, get all the answers you need to get your job done.