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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 time10 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

Maintaining a driveway depends on its material. For concrete and asphalt, it's best to clean the surface thoroughly twice a year with a stiff broom and a pressure washer to remove accumulated dirt and debris. Sealing the driveway is crucial to protect it from water damage and freeze-thaw cycles. Before applying a sealant, pressure wash the surface to remove any loose sealant, dirt, or stains, as sealing over them will trap them. Any cracks or expansion joints should be filled with a flexible polyurethane caulk or asphalt sealer. In colder climates, use sand instead of salt for de-icing. Sand helps melt snow and ice without accelerating the freeze-thaw process, which can cause cracks.

Yes, recycled asphalt driveway costs can be substantially lower than new asphalt. With new asphalt costing between $90 and $190 per ton, this option can cost as much as 10 times more than laying down asphalt millings.

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.

While paving a driveway is possible to do as a DIY project, we don’t recommend it. Hiring a driveway professional to pave it will ensure that your driveway looks neat and clean and lasts for years to come, and it will also prevent a weak driveway and, potentially, damage to your foundation. Paving a driveway requires heavy machinery, and while you can rent the equipment needed, operating it close to your garage slab or around your home’s foundation can crack it and lead to structural issues. 

Depending on project size, typically 1 to 3 days, including preparation and installation.

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.