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TRUSTED BY CHESTERTOWN, MD HOMEOWNERS

  • Average homeowner rating star icon4.8
    Average homeowner rating
  • Verified reviews icon21
    Verified paving services reviews

Top-Rated Paving pros in Chestertown - Updated Nov 2026

Avatar for Robert & Son Paving
Robert & Son Paving
4.8(
93
)
Gravel or Loose Fill Paving - Install, Spread or ScrapeAsphalt Paving - InstallAsphalt Paving - Install- For Business

Serving Chestertown, MD and surrounding areas

Approved

Super Service Award Winner

In business since 1955

Free estimates

Credit card accepted

"Everything was perfect from start to finish. The price was competitive. The attention to detail was beyond my expectations and the job looked beautiful when it was done. Recommend this company highly for any paving needs to have."
Paved
Paved
Paved
Seal Coat
Seal Coat

+38

Response time9 hrs
2 neighbors recently requested a quote
Recommended by72%of homeowners
Avatar for Evans Paving
Evans Paving
4.2(
85
)
Asphalt Paving - Repair or PatchAsphalt Paving - InstallAsphalt Paving - Install- For Business+1 more

Serving Chestertown, MD and surrounding areas

Approved

In business since 1974

Free estimates

Emergency services offered

"Tom C. ⭐️⭐️⭐️⭐️⭐️ Excellent Service from Evans Paving, LLC I couldn’t be more impressed with the outstanding work Evans Paving did on our challenging driveway. They professionally paved over 1,500 feet of driveway, including two large parking pads, pitched driveway for water runoff and completely transformed our property. Their team didn’t just pave — they went the extra mile by removing and cutting away invasive tree roots that had destroyed the old driveway. The attention to detail was clear from start to finish, and they sealed the entire project beautifully, leaving us with a clean, smooth driveway. Every step of the project was handled with professionalism, quality and attention to detail at a very reasonable price. If you’re looking for quality work, a reliable crew, and a reasonable price, Evans Paving is the team to call. We already recommended them to our family and friends."
Tar n chip
Tar and chip driveway
Tar and chip
Parking lot
Parking lot

+17

Response time2 days
2 neighbors recently requested a quote
Recommended by88%of homeowners
Zweemers Paving and Sealcoating
4.4(
34
)
Asphalt Paving - InstallAsphalt Paving - Install- For BusinessAsphalt Paving - Repair or Patch+1 more

Serving Chestertown, MD and surrounding areas

Approved

In business since 1995

Free estimates

Emergency services offered

"Jimmy and his crew were on time, worked well together and completed our driveway in a professional and orderly fashion. I would strongly recommend Zweemer paving Mason E"
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+10

Response time2 days
Response rate100%
3 neighbors recently requested a quote
DDC Property Maintenance LLC
4.4(
11
)
Gravel or Loose Fill Paving - Install, Spread or Scrape

Serving Chestertown, MD and surrounding areas

Approved

In business since 2018

Free estimates

Offers commercial services

"Wilson prepped the pad for our barndominium, installed our bioswale, helped with tree removal, Installed our septic, and did our driveway for our custom home build. He was great with dealing with the county for us and made things smooth and easy. All work exceeded our expectations. Great guy and it was great to support a small local family in our area."
Response time2 days
7 neighbors recently requested a quote
Recommended by70%of homeowners
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Paving Services FAQs, answered by experts

Interlocking pavers offer a number of advantages over regular pavers. For instance, they’re more durable, more resistant to shifting, and easier to repair. There are also permeable options that allow for drainage. However, interlocking pavers are more often more expensive than regular pavers and are prone to growing weeds over time.

An asphalt driveway should be at least 3 inches thick over a compacted gravel base. Areas with poor drainage should have a thicker stone base. To install a new asphalt driveway over an existing driveway, the new asphalt should be at least 2 inches thick and the existing driveway should be in relatively good condition.

The stones do not work well on uneven ground. If the stones are not buried into the ground and made level upon installation, they almost certainly will shift or crack on uneven ground. Additionally, rainwater or water from sprinklers can run under the edge of an uneven paver, causing erosion. In a freeze and thaw cycle, trapped water under the paver can cause the problem to worsen by shifting the stepping stones around. Use a bubble level to make sure the ground under each paver is as even as possible, even if the nearby ground is uneven.

Driveway paving costs around $4,500 on average, but depending on many factors, you could pay anywhere from $2,500 to $6,600 or more. The size of your driveway will usually be the most significant factor, with more square footage increasing your costs. You can expect to pay between $2 and $15 per square foot for paving services. Some other factors that play a role include the following:

  • Quality of the materials

  • Contractor’s experience and expertise

  • Site preparation and grading, if necessary

  • Layout of your driveway

Outdoor kitchens get wet and are sometimes next to pools. To avoid accidents, go with a non-slip material like concrete, brick, or rubber. Avoid materials like ceramic and porcelain, as they are known to be quite slippery. Wood and composite flooring can be slippery if untreated, so make sure to stain or finish these materials.

The Chestertown, MD homeowners’ guide to paving services

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