40 Main St Suite 101, Florence, MA 01062
Paving & Driveways in Chesterfield, Massachusetts
Compare contractors serving Chesterfield, Hampshire County — call them directly, or send one request and let qualified pros come to you.
50 contractors serving Chesterfield.
Contractors serving Chesterfield
- Dodson & Flinker, IncServes Chesterfield · 9.3 mi★★★★★4.5 rating
- Better PathwaysServes Chesterfield · 11.0 mi★★★★★5.0 rating
138 Fomer Rd # A, Southampton, MA 01073
- Geeleher Enterprises IncServes Chesterfield · 11.4 mi★★★★★5.0 rating
39 College Hwy, Southampton, MA 01073
- Beyond Landscape ContractingServes Chesterfield · 11.7 mi★★★★☆4.4 rating
83 State Rd, South Deerfield, MA 01373
- Serves Chesterfield · 12.6 mi
98 Main St, Hatfield, MA 01038
- Serves Chesterfield · 13.8 mi
81 Valley Rd, Southampton, MA 01073
- Barko's | Excavating & Material DeliveryServes Chesterfield · 14.8 mi★★★★★4.7 rating
71 San Souci Dr, South Hadley, MA 01075
- Valley ExcavatingServes Chesterfield · 14.8 mi★★★★★4.9 rating
39 Knightly Rd, Hadley, MA 01035
- Chagnon Building & Remodeling, LLCServes Chesterfield · 14.9 mi★★★★★4.6 rating
91 Stockbridge St, Hadley, MA 01035
- Ethan's Eden Landscape and Design, LLCServes Chesterfield · 15.0 mi★★★★★5.0 rating
21 N Maple St, Hadley, MA 01035
- J.L. Raymaakers & Sons, Inc.Serves Chesterfield · 15.4 mi★★★★☆3.9 rating
109 Falcon Dr, Westfield, MA 01085
- Always Reliable Excavating IncServes Chesterfield · 16.3 mi★★★★★4.8 rating
35 Fairlawn St, South Hadley, MA 01075
- RJM Landscaping, IncServes Chesterfield · 16.5 mi★★★★★5.0 rating
13 Airport Dr, Westfield, MA 01085
- G & H Landscaping, Inc.Serves Chesterfield · 17.0 mi★★★★☆4.3 rating
58 Commercial St, Holyoke, MA 01040
- Amherst ExcavatingServes Chesterfield · 17.4 mi★★★★★5.0 rating
256 S East St, Amherst, MA 01002
- Serves Chesterfield · 17.7 mi
50 W State St, Granby, MA 01033
- Keiter CorporationServes Chesterfield · 18.2 mi★★★★★4.9 rating
1 Interstate Dr, West Springfield, MA 01089
- Ocare Landscaping & Lawn CareServes Chesterfield · 18.3 mi★★★★★4.9 rating
20 Chestnut St, Westfield, MA 01085
- Crack ManServes Chesterfield · 19.0 mi★★★★★4.6 rating
14 Clifton St, Westfield, MA 01085
- Integrastone LandscapingServes Chesterfield · 19.5 mi★★★★★5.0 rating
1589 East St Suite C, Pittsfield, MA 01201
- We Landscape LLCServes Chesterfield · 19.7 mi★★★★★5.0 rating
149 Cave Hill Rd, Leverett, MA 01054
- Rockland Masonry & RestorationServes Chesterfield · 19.7 mi★★★★☆4.0 rating
1500 East St suite c, Pittsfield, MA 01201
- H.A. O'Neil Masonry, LLCServes Chesterfield · 19.8 mi★★★★★4.8 rating
1478 East St, Pittsfield, MA 01201
- Rapid Quality Construction LLCServes Chesterfield · 20.1 mi★★★★★5.0 rating
1129 Riverdale St #1016, West Springfield, MA 01089
- Ondrick Natural EarthServes Chesterfield · 21.1 mi★★★★★4.7 rating
729 Fuller Rd, Chicopee, MA 01020
- Ondrick Materials & RecyclingServes Chesterfield · 21.2 mi★★★★★4.8 rating
22 Industry Rd, Chicopee, MA 01020
- LB CorporationServes Chesterfield · 21.6 mi★★★★★4.8 rating
95 Marble St, Lee, MA 01238
- JAF ContractingServes Chesterfield · 21.8 mi★★★★★5.0 rating
346 Wahconah St, Pittsfield, MA 01201
- CMJ Paving & Landscaping INCServes Chesterfield · 22.1 mi★★★★☆4.1 rating
20 Oakdale St, Springfield, MA 01104
- The Hardscape CompanyServes Chesterfield · 22.4 mi★★★★★5.0 rating
9 Cedar St, Southwick, MA 01077
- First Peak ConstructionServes Chesterfield · 22.4 mi★★★★★5.0 rating
425 Union St Unit 13, West Springfield, MA 01089
- Cosgrove ConstructionServes Chesterfield · 22.6 mi★★★★★4.6 rating
77 Heywood Ave, West Springfield, MA 01089
- Serves Chesterfield · 22.7 mi
70 Windsor St, West Springfield, MA 01089
- Pioneer Stone SealsServes Chesterfield · 22.9 mi★★★★★5.0 rating
112 S Prospect St, Millers Falls, MA 01349
- Louis A Pallotta Asphalt PavingServes Chesterfield · 22.9 mi★★★★☆4.1 rating
15 Keating Ln, Agawam, MA 01001
- By Design Landscape Concepts, Inc.Serves Chesterfield · 23.0 mi★★★★☆4.2 rating
50 Russo Cir, Agawam, MA 01001
- Air Sweep IncServes Chesterfield · 23.0 mi★★★★★4.5 rating
54 Russo Cir, Agawam, MA 01001
- JL Construction CorpServes Chesterfield · 23.1 mi★★★☆☆3.4 rating
203 Circuit Ave, West Springfield, MA 01089
- City Enterprise IncServes Chesterfield · 23.4 mi★★★★★5.0 rating
52-60 Berkshire Ave, Springfield, MA 01109
- ACME Site Work Inc.Serves Chesterfield · 23.5 mi★★★★☆4.4 rating
33 Albert Ave, Indian Orchard, MA 01151
- Superior Sealcoat & Asphalt RepairServes Chesterfield · 23.9 mi★★★★★5.0 rating
45 Santa Maria St, Pittsfield, MA 01201
- Haluch's Landscaping ProductsServes Chesterfield · 23.9 mi★★★★★4.5 rating
1014 Center St, Ludlow, MA 01056
- Polnorth Contractors Inc.Serves Chesterfield · 24.0 mi★☆☆☆☆1.0 rating
2 River Rd, Wilbraham, MA 01095
- Witch Enterprises IncServes Chesterfield · 24.2 mi★★★★★4.5 rating
467 Silver St, Agawam, MA 01001
- State Line PavingServes Chesterfield · 24.2 mi★★★★★5.0 rating
2 S Bridge Dr, Agawam, MA 01001
- Olies Concrete Contractors LLCServes Chesterfield · 25.6 mi★★★★★5.0 rating
61 Clearbrook Dr, Springfield, MA 01118
- Dave Ryan LandscapesServes Chesterfield · 26.3 mi★★★★★5.0 rating
60 Ravenwood Dr suite B, Ludlow, MA 01056
- Serves Chesterfield · 26.5 mi
24 Scacebrook Rd, Pittsfield, MA 01201
- Williams PavingServes Chesterfield · 27.3 mi★★★★★5.0 rating
52 Great Barrington Rd, West Stockbridge, MA 01266
- Ace Asphalt PavingServes Chesterfield · 27.7 mi★★★★★4.8 rating
997 Tinkham Rd, Wilbraham, MA 01095
Paving & Driveways in Chesterfield — what to know
Rebates & incentives
Mass Save covers heating and water heating, not paving, so there is no driveway rebate in Chesterfield. The relevant local concern is permits and drainage. A new or widened drive tying into a town road needs a curb-cut or driveway permit from the DPW or building department, and any cut into the road surface requires a street-opening permit.
Chesterfield is served by National Grid, not a municipal light plant, but that's an electric-service distinction with no effect on paving. With the Westfield River, Chesterfield Gorge, brooks, and wetlands across the highlands, adding impervious surface near water can require Conservation Commission review under the Wetlands Protection Act, and the town's steep terrain makes drainage and frost durability central.
Permits in Chesterfield
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 Chesterfield, a new or widened driveway connecting to a town road needs a curb-cut or driveway permit, and opening the traveled way requires a street-opening permit. New impervious area near the Westfield River, brooks, or mapped wetlands can trigger Conservation Commission review under the Wetlands Protection Act. Permit fees vary by cycle, so confirm current amounts with town hall first.
Typical project cost
Western Massachusetts hilltown paving runs below Boston-metro rates, though Chesterfield's steep grades, long rural drives, and remote hauls can raise totals. A new asphalt driveway typically runs $4,500–$12,000, with long steep drives landing at the upper end. Sealcoating runs about $250–$700. Concrete drives run roughly $8–$18 per square foot. The main cost drivers are slope and length, gravel-to-asphalt conversion, the depth of frost-damaged base repair over rocky soils, and drainage work to handle hilltown snowmelt.
About Chesterfield homes
Chesterfield is a Hampshire County hilltown of about 996 residents across roughly 504 housing units, west of Northampton in the highlands above the Westfield River. The housing averages around 53 years old, with homes on large wooded lots and long approach drives off roads like Route 143 and Main Road.
Those long hill drives are the bulk of local paving work. Hilltown freeze-thaw over rocky soils produces sub-base failure and frost cracking, so rebuilding bases, regrading for drainage, and converting washed-out gravel drives to asphalt are the recurring jobs in Chesterfield.
Common questions — Paving & Driveways in Chesterfield
- Do I need a permit to pave my driveway in Chesterfield?
- A new or widened tie-in to a town road needs a curb-cut or driveway permit from the DPW or building department, and a cut into the road surface needs a street-opening permit. A resurface inside your existing drive usually doesn't.
- I'm near the Westfield River or the Gorge — will that affect paving?
- It can. Adding impervious surface near the river, brooks, or wetlands may require Conservation Commission review under the Wetlands Protection Act, particularly for a new or expanded driveway in this protected corridor.
- Does Mass Save help pay for a driveway in Chesterfield?
- No. Mass Save funds only heating, cooling, and water heating. Paving isn't eligible, whether you're a National Grid customer or not.
- Should I convert my long gravel drive to asphalt?
- Many Chesterfield owners do to stop washouts and regrading, but the base and drainage must be built right first. Paving over saturated hill soil without that work just traps water and invites frost heave.
- Why does my driveway crack near the top of the slope?
- Hill grades concentrate runoff that undermines the base, and freeze-thaw lifts it from below. Regrading to carry water away and rebuilding the sub-base on the slope is the durable fix, not a surface patch.
