138 Fomer Rd # A, Southampton, MA 01073
Paving & Driveways in Chester, Massachusetts
Compare contractors serving Chester, Hampden County — call them directly, or send one request and let qualified pros come to you.
50 contractors serving Chester.
Contractors serving Chester
- Better PathwaysServes Chester · 9.1 mi★★★★★5.0 rating
- Serves Chester · 12.0 mi
81 Valley Rd, Southampton, MA 01073
- Geeleher Enterprises IncServes Chester · 12.0 mi★★★★★5.0 rating
39 College Hwy, Southampton, MA 01073
- J.L. Raymaakers & Sons, Inc.Serves Chester · 12.8 mi★★★★☆3.9 rating
109 Falcon Dr, Westfield, MA 01085
- RJM Landscaping, IncServes Chester · 13.4 mi★★★★★5.0 rating
13 Airport Dr, Westfield, MA 01085
- Ocare Landscaping & Lawn CareServes Chester · 13.7 mi★★★★★4.9 rating
20 Chestnut St, Westfield, MA 01085
- Dodson & Flinker, IncServes Chester · 14.3 mi★★★★★4.5 rating
40 Main St Suite 101, Florence, MA 01062
- Crack ManServes Chester · 15.0 mi★★★★★4.6 rating
14 Clifton St, Westfield, MA 01085
- LB CorporationServes Chester · 16.3 mi★★★★★4.8 rating
95 Marble St, Lee, MA 01238
- Keiter CorporationServes Chester · 16.6 mi★★★★★4.9 rating
1 Interstate Dr, West Springfield, MA 01089
- Barko's | Excavating & Material DeliveryServes Chester · 16.6 mi★★★★★4.7 rating
71 San Souci Dr, South Hadley, MA 01075
- The Hardscape CompanyServes Chester · 16.9 mi★★★★★5.0 rating
9 Cedar St, Southwick, MA 01077
- G & H Landscaping, Inc.Serves Chester · 17.2 mi★★★★☆4.3 rating
58 Commercial St, Holyoke, MA 01040
- Always Reliable Excavating IncServes Chester · 18.1 mi★★★★★4.8 rating
35 Fairlawn St, South Hadley, MA 01075
- Rapid Quality Construction LLCServes Chester · 18.4 mi★★★★★5.0 rating
1129 Riverdale St #1016, West Springfield, MA 01089
- Serves Chester · 18.9 mi
98 Main St, Hatfield, MA 01038
- Integrastone LandscapingServes Chester · 19.0 mi★★★★★5.0 rating
1589 East St Suite C, Pittsfield, MA 01201
- Rockland Masonry & RestorationServes Chester · 19.1 mi★★★★☆4.0 rating
1500 East St suite c, Pittsfield, MA 01201
- H.A. O'Neil Masonry, LLCServes Chester · 19.2 mi★★★★★4.8 rating
1478 East St, Pittsfield, MA 01201
- Beyond Landscape ContractingServes Chester · 19.3 mi★★★★☆4.4 rating
83 State Rd, South Deerfield, MA 01373
- Serves Chester · 20.0 mi
50 W State St, Granby, MA 01033
- Louis A Pallotta Asphalt PavingServes Chester · 20.0 mi★★★★☆4.1 rating
15 Keating Ln, Agawam, MA 01001
- Cosgrove ConstructionServes Chester · 20.1 mi★★★★★4.6 rating
77 Heywood Ave, West Springfield, MA 01089
- First Peak ConstructionServes Chester · 20.2 mi★★★★★5.0 rating
425 Union St Unit 13, West Springfield, MA 01089
- By Design Landscape Concepts, Inc.Serves Chester · 20.2 mi★★★★☆4.2 rating
50 Russo Cir, Agawam, MA 01001
- Air Sweep IncServes Chester · 20.2 mi★★★★★4.5 rating
54 Russo Cir, Agawam, MA 01001
- Serves Chester · 20.3 mi
70 Windsor St, West Springfield, MA 01089
- Ethan's Eden Landscape and Design, LLCServes Chester · 20.7 mi★★★★★5.0 rating
21 N Maple St, Hadley, MA 01035
- Witch Enterprises IncServes Chester · 20.8 mi★★★★★4.5 rating
467 Silver St, Agawam, MA 01001
- JL Construction CorpServes Chester · 20.8 mi★★★☆☆3.4 rating
203 Circuit Ave, West Springfield, MA 01089
- Ondrick Natural EarthServes Chester · 21.0 mi★★★★★4.7 rating
729 Fuller Rd, Chicopee, MA 01020
- Ondrick Materials & RecyclingServes Chester · 21.0 mi★★★★★4.8 rating
22 Industry Rd, Chicopee, MA 01020
- JAF ContractingServes Chester · 21.2 mi★★★★★5.0 rating
346 Wahconah St, Pittsfield, MA 01201
- Chagnon Building & Remodeling, LLCServes Chester · 21.3 mi★★★★★4.6 rating
91 Stockbridge St, Hadley, MA 01035
- Valley ExcavatingServes Chester · 21.4 mi★★★★★4.9 rating
39 Knightly Rd, Hadley, MA 01035
- CMJ Paving & Landscaping INCServes Chester · 21.9 mi★★★★☆4.1 rating
20 Oakdale St, Springfield, MA 01104
- State Line PavingServes Chester · 22.0 mi★★★★★5.0 rating
2 S Bridge Dr, Agawam, MA 01001
- Superior Sealcoat & Asphalt RepairServes Chester · 22.2 mi★★★★★5.0 rating
45 Santa Maria St, Pittsfield, MA 01201
- Williams PavingServes Chester · 22.5 mi★★★★★5.0 rating
52 Great Barrington Rd, West Stockbridge, MA 01266
- City Enterprise IncServes Chester · 22.6 mi★★★★★5.0 rating
52-60 Berkshire Ave, Springfield, MA 01109
- Amherst ExcavatingServes Chester · 23.1 mi★★★★★5.0 rating
256 S East St, Amherst, MA 01002
- ACME Site Work Inc.Serves Chester · 23.5 mi★★★★☆4.4 rating
33 Albert Ave, Indian Orchard, MA 01151
- Serves Chester · 23.9 mi
24 Scacebrook Rd, Pittsfield, MA 01201
- Pete's Sales & ServiceServes Chester · 24.4 mi★★★★☆4.0 rating
69 S Main St, Sheffield, MA 01257
- Polnorth Contractors Inc.Serves Chester · 24.5 mi★☆☆☆☆1.0 rating
2 River Rd, Wilbraham, MA 01095
- Olies Concrete Contractors LLCServes Chester · 24.6 mi★★★★★5.0 rating
61 Clearbrook Dr, Springfield, MA 01118
- Haluch's Landscaping ProductsServes Chester · 25.5 mi★★★★★4.5 rating
1014 Center St, Ludlow, MA 01056
- Dave Ryan LandscapesServes Chester · 27.4 mi★★★★★5.0 rating
60 Ravenwood Dr suite B, Ludlow, MA 01056
- Ace Asphalt PavingServes Chester · 27.5 mi★★★★★4.8 rating
997 Tinkham Rd, Wilbraham, MA 01095
- We Landscape LLCServes Chester · 27.6 mi★★★★★5.0 rating
149 Cave Hill Rd, Leverett, MA 01054
Paving & Driveways in Chester — what to know
Rebates & incentives
Mass Save does not apply to paving, which covers neither heating nor water heating, so there is no driveway rebate here. Worth noting: Chester is served by the Chester Municipal Light Plant, a municipal utility, which means residents are outside Mass Save's investor-owned territory and not eligible for its energy rebates at all — but that distinction is about electricity and heating, not paving, where no rebate exists for anyone regardless of utility.
The local angle that does matter is permits and drainage. A new or widened drive tying into a town road needs a curb-cut or driveway permit from the Chester DPW or building department, a Route 20 tie-in can require MassDOT review, and adding impervious surface near the Westfield River branches or wetlands can trigger Conservation Commission review under the Wetlands Protection Act.
Permits in Chester
Massachusetts has no statewide paving license, but residential paving contractors must hold Home Improvement Contractor (HIC) registration, with a Construction Supervisor License for structural work. In Chester, a new or widened driveway connecting to a town road needs a curb-cut or driveway permit, opening the traveled way requires a street-opening permit, and a tie-in onto Route 20 can need MassDOT approval. New impervious area near the Westfield River branches, brooks, or mapped wetlands can trigger Conservation Commission review under the Wetlands Protection Act. Permit fees vary by cycle.
Typical project cost
Western Massachusetts hill-country paving runs below Boston-metro rates, but Chester's steep grades, narrow lots, and remote hauls can raise totals. A new asphalt driveway typically runs $4,500–$12,000 depending on length and slope. Sealcoating runs about $250–$700. Concrete drives run roughly $8–$18 per square foot. The main cost drivers are slope, tear-out versus overlay, the depth of frost-damaged base repair over rocky soils, and drainage work to handle runoff on steep riverside lots.
About Chester homes
Chester is a Hampden County hill town of about 1,403 residents across roughly 689 housing units, set in the Westfield River valley along Route 20 west of Huntington. The housing stock averages around 71 years old, much of it older homes on steep, narrow lots near the river and rail line.
The terrain defines local paving: steep approach drives, narrow road frontages, and runoff toward the Westfield River branches. Hill-country freeze-thaw over rocky and clay soils produces sub-base failure and frost cracking, so rebuilding bases, regrading for drainage, and reworking crumbling aprons are the recurring jobs in Chester.
Common questions — Paving & Driveways in Chester
- I'm in Chester — does my municipal utility change anything for paving?
- No. Chester is served by the Chester Municipal Light Plant, which keeps residents out of Mass Save energy rebates, but Mass Save never covered paving for anyone anyway. Paving rules here come down to local curb-cut and wetlands permits, not your electric provider.
- Do I need a permit to pave my driveway in Chester?
- A new or widened tie-in to a town road needs a curb-cut or driveway permit from the DPW or building department, a cut into the road needs a street-opening permit, and a Route 20 tie-in can require MassDOT approval. A resurface inside your existing drive usually doesn't.
- Why does my steep driveway crack near the top every spring?
- Steep hill grades concentrate runoff that undermines the base, and freeze-thaw lifts it from below. Regrading for drainage and rebuilding the sub-base on the slope is the lasting fix, not a surface patch.
- I'm near the Westfield River — will that affect my project?
- It can. Adding impervious surface near the river branches, brooks, or wetlands may require Conservation Commission review under the Wetlands Protection Act, especially for a new or expanded driveway.
- How long should a new asphalt driveway last in Chester?
- With a properly built base and good drainage, 15 to 20 years is realistic, though hard hill-country freeze-thaw shortens that if water reaches the base. Sealcoating every few years and filling cracks promptly extends its life.
