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  • 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
)
Interior Painting or Staining: 5 + RoomsExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+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%
3 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 Paint Works LLC
Paint Works LLC
5.0(
5
)
Interior Painting or Staining: 5 + RoomsExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+4 more

Serving Trail, OR and surrounding areas

Approved

Super Service Award Winner

In business since 2023

Free estimates

Small jobs welcome

"Patrick with Paint Works LLC painted our home late last summer and did a fantastic job! I am very meticulous with the quality of work I want accomplished and Patrick certainly delivered! We are very happy with the end result and highly recommend him!"
My Jobs
My Jobs
My Jobs
My Jobs
My Jobs

+1

Response time2 days
1 neighbors recently requested a quote
Recommended by20%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

Whitewashing isn’t permanent, but it can last for a long, long time. When you apply it correctly or have a seasoned pro whitewash your brick, whitewashing can last for 20 to 30 years or longer. Whitewash is very durable and typically requires little maintenance, making it a great project for most DIYers.

A properly applied coat of stain will last between 3 and 8 years, depending on your climate. If you live in a place where your fence experiences a lot of moisture or high heat, your stain will last for a shorter period than in more temperate conditions. We recommend reapplying stain every 3 to 5 years to keep your wood in good condition.

Regular cleaning, touch-ups for small defects, and resealing or repainting every 2-3 years help to maintain a vibrant appearance and protection.

The number of coats you need to apply when whitewashing a surface depends on how opaque you want the final product to be. If you're going for a transparent, barely there look, a single coat or two may suffice. For fuller coverage, you'll want to use multiple coats. Another option is to use a less diluted paint to get a thicker coverage. 

While the answer varies based on weather, 10 a.m. is a good time to start painting. The dew will have dried, meaning there’s no moisture on the house, and the temperature will likely be moderate and the sunlight less direct. Starting mid-morning should also give you enough daylight and pleasant weather to work on the job for several hours.

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.