39 College Hwy, Southampton, MA 01073
Paving & Driveways in Montgomery, Massachusetts
Compare contractors serving Montgomery, Hampden County — call them directly, or send one request and let the ones who want the job come to you.
30 contractors serving Montgomery.
Contractors serving Montgomery
Claimed listings within 5 miles come first, then the rest by rating, then distance. Google ratings as of October 2026. How we list and rank contractors
- Geeleher Enterprises IncServes Montgomery · 7.2 mi★★★★★5.0 Google rating
- The Hardscape CompanyServes Montgomery · 11.7 mi★★★★★5.0 Google rating
9 Cedar St, Southwick, MA 01077
- Rapid Quality Construction LLCServes Montgomery · 12.3 mi★★★★★5.0 Google rating
1129 Riverdale St #1016, West Springfield, MA 01089
- First Peak ConstructionServes Montgomery · 14.0 mi★★★★★5.0 Google rating
425 Union St Unit 13, West Springfield, MA 01089
- State Line PavingServes Montgomery · 15.9 mi★★★★★5.0 Google rating
2 S Bridge Dr, Agawam, MA 01001
- City Enterprise IncServes Montgomery · 16.6 mi★★★★★5.0 Google rating
52-60 Berkshire Ave, Springfield, MA 01109
- Olies Concrete Contractors LLCServes Montgomery · 18.5 mi★★★★★5.0 Google rating
61 Clearbrook Dr, Springfield, MA 01118
- JAF ContractingServes Montgomery · 27.3 mi★★★★★5.0 Google rating
346 Wahconah St, Pittsfield, MA 01201
- Williams PavingServes Montgomery · 28.2 mi★★★★★5.0 Google rating
52 Great Barrington Rd, West Stockbridge, MA 01266
- Superior Sealcoat & Asphalt RepairServes Montgomery · 28.3 mi★★★★★5.0 Google rating
45 Santa Maria St, Pittsfield, MA 01201
- Pioneer Stone SealsServes Montgomery · 30.5 mi★★★★★5.0 Google rating
112 S Prospect St, Millers Falls, MA 01349
- Property Masters Driveway Repair and MaintenanceServes Montgomery · 31.1 mi★★★★★5.0 Google rating
33 Hardwick Pond Rd, Ware, MA 01082
- Keiter CorporationServes Montgomery · 10.5 mi★★★★★4.9 Google rating
1 Interstate Dr, West Springfield, MA 01089
- Ace Asphalt PavingServes Montgomery · 21.5 mi★★★★★4.8 Google rating
997 Tinkham Rd, Wilbraham, MA 01095
- LB CorporationServes Montgomery · 22.0 mi★★★★★4.8 Google rating
95 Marble St, Lee, MA 01238
- APMI Asphalt Paving & MaintenanceServes Montgomery · 27.9 mi★★★★★4.7 Google rating
113 Bethany Rd, Monson, MA 01057
- Stanley & Sons PavingServes Montgomery · 29.2 mi★★★★★4.7 Google rating
62 Munn Rd, Monson, MA 01057
- Crack ManServes Montgomery · 9.1 mi★★★★★4.6 Google rating
14 Clifton St, Westfield, MA 01085
- Cosgrove ConstructionServes Montgomery · 13.9 mi★★★★★4.6 Google rating
77 Heywood Ave, West Springfield, MA 01089
- Witch Enterprises IncServes Montgomery · 14.8 mi★★★★★4.5 Google rating
467 Silver St, Agawam, MA 01001
- Henry's PavingServes Montgomery · 36.6 mi★★★★☆4.4 Google rating
223 Brookfield Rd, Sturbridge, MA 01518
- Louis A Pallotta Asphalt PavingServes Montgomery · 13.9 mi★★★★☆4.1 Google rating
15 Keating Ln, Agawam, MA 01001
- CMJ Paving & Landscaping INCServes Montgomery · 15.9 mi★★★★☆4.1 Google rating
20 Oakdale St, Springfield, MA 01104
- Pete's Sales & ServiceServes Montgomery · 27.9 mi★★★★☆4.0 Google rating
69 S Main St, Sheffield, MA 01257
- J.L. Raymaakers & Sons, Inc.Serves Montgomery · 6.7 mi★★★★☆3.9 Google rating
109 Falcon Dr, Westfield, MA 01085
- JL Construction CorpServes Montgomery · 14.7 mi★★★☆☆3.4 Google rating
203 Circuit Ave, West Springfield, MA 01089
- Polnorth Contractors Inc.Serves Montgomery · 18.6 mi★☆☆☆☆1.0 Google rating
2 River Rd, Wilbraham, MA 01095
- Serves Montgomery · 14.2 mi
70 Windsor St, West Springfield, MA 01089
- Serves Montgomery · 14.9 mi
50 W State St, Granby, MA 01033
- Serves Montgomery · 16.4 mi
98 Main St, Hatfield, MA 01038
Paving & Driveways in Montgomery — what to know
Rebates & incentives
Mass Save has nothing to do with paving — it funds heating, cooling, and weatherization, not driveways — so there is no paving rebate in Montgomery, even though it sits in Eversource territory and qualifies for Mass Save energy work. The rules that govern a driveway are local. Montgomery requires a driveway and curb-cut permit and a street-opening permit through the highway department before a new or widened drive connects to a town road.
The town's streams feed the Westfield River, so lots near water or wetlands can trigger Conservation Commission review under the Wetlands Protection Act, and added impervious surface may need to manage runoff. On Montgomery's grades the practical concern is drainage paired with a base built for deep frost — a hillside drive that doesn't shed water heaves and cracks fast.
Permits in Montgomery
Massachusetts has no paving license, but residential paving contractors must carry a state Home Improvement Contractor (HIC) registration, and structural retaining walls on sloped lots require a licensed Construction Supervisor. In Montgomery the highway department issues driveway and curb-cut permits, and tying into a town road needs a street-opening permit and inspection. Lots near a stream or wetland may require a Conservation Commission filing under the Wetlands Protection Act first. Fees are modest and set per recent cycles; a contractor familiar with the Westfield-area hilltowns handles the public-way and conservation steps.
Typical project cost
Paving in the Hampden County hilltowns runs unevenly against the statewide band: lower labor than Boston metro, but travel from Westfield-area plants and steep, ledge-prone lots add haul and excavation cost. A standard asphalt driveway install typically runs $4,500–$12,000, with long hillside drives near the top. Sealcoating generally runs $250–$700. Concrete is around $8–$18 per square foot, and permeable pavers higher. Slope, drive length, sub-base repair, and the drainage required to survive freeze-thaw are the main cost drivers.
About Montgomery homes
Montgomery is a small Hampden County hilltown of about 877 residents and just 404 housing units, perched in the hills above Westfield near Russell, Huntington, and Southampton. The median home is around 47 years old, younger than the old river-valley towns because much of Montgomery built out as rural residential lots later in the 20th century.
That means a lot of newer homes on long, sloped, wooded drives feeding off Route 66 and narrow town roads. Paving work is dominated by grade and drainage: steep approaches, deep roadside ditches, and frost. Many owners pave a solid apron and the steepest section and keep the back stretch as gravel.
Common questions — Paving & Driveways in Montgomery
- Do I need a permit to pave a driveway in Montgomery?
- For a new or widened connection to a town road, yes — Montgomery's highway department issues a driveway and curb-cut permit and a street-opening permit with inspection. Repaving an existing drive in place usually does not require one.
- Why does my Montgomery driveway heave in winter?
- Hill-country freeze-thaw and water under a thin base lift the asphalt. A deeper compacted base and ditching that carries meltwater off the grade outlast a thicker top coat.
- Can I pave only the steep part of my drive?
- Yes. Many Montgomery owners pave the apron and steepest pitch for traction and keep the rest gravel. A paver builds a solid transition and a drainage swale where pavement meets gravel.
- Do I need Conservation Commission approval near a stream?
- Possibly. If your lot is near a stream or wetland feeding the Westfield River, adding impervious driveway surface can trigger a Wetlands Protection Act filing with the Montgomery Conservation Commission.
- Is there a rebate for paving in Montgomery?
- No. Mass Save pays only for heating, cooling, and weatherization, never paving, and Massachusetts has no statewide driveway rebate.
