Living in the Berkshires means your roof takes a beating. Heavy snow loads, ice dams, freeze-thaw cycles, and summer storms are all part of life here and they all wear on your roof faster than in most parts of the country.
When it’s finally time to replace or repair your roof, homeowners in Berkshire County often feel the same anxiety: Who can I actually trust with this?
At Adam Quenneville Roofing & Siding, we’ve been helping homeowners across Western MA throughout Berkshire County for over 30 years. And one question comes up all the time:
“If we don’t choose you, who else would you recommend in the Berkshires?”
Roofing is a big decision. We believe trust is built on transparency, so yes, this article includes other reputable roofing contractors in our area.
Because at the end of the day, the right roofer is the one who’s the best fit for your home, your budget, and your expectations, even if that’s not us.
This guide will help you make that decision with confidence.
By the end of this article, you’ll know:
- What makes a roofing contractor reputable and trustworthy in the Berkshires
- The unique roofing challenges of Berkshire County
- How we evaluated the contractors on this list
- Detailed insights into the top 6 roofing companies in Berkshire County (in alphabetical order, except our own at the end)
- How to avoid roofing scams and high-pressure sales tactics
- How to choose the roofer that fits your needs
Let’s start with the biggest question.
What Makes a Great Roofing Contractor in Berkshire County?
Not every roofer is equipped for the climate, regulations, or architectural styles of New England homes. Here’s what matters most when hiring a roofer in the Berkshires.
Proper Licensing & Insurance. A roofer should always carry active liability insurance and workers’ compensation. This protects you from surprise costs if an accident happens on your property. Always ask for proof before signing anything.
Experience With Berkshire Weather. Our roofs face freeze-thaw cycles, ice dams, heavy snowfall (especially in Northern Berkshire County), high winds, and humidity-driven algae growth. You want someone who builds roofs specifically designed to withstand this climate, not a contractor who learned their trade somewhere else and is figuring it out here.
Google Reviews & Local Reputation. Look for consistent patterns: reliability, clean job sites, strong communication, and warranty follow-through. One 5-star review doesn’t matter. Dozens or hundreds of them do.
Strong Warranty Coverage. This means both a manufacturer’s warranty on materials and a workmanship guarantee from the contractor. A warranty is only as good as the company standing behind it.
Transparent Pricing. Clear estimates, line items, and flexible payment options help you understand exactly what you’re investing in. If a contractor won’t break down their quote, that’s a warning sign.
Professional Communication. A great roofer answers questions, shows up when they say they will, provides clear expectations, and respects your time and home.
Thorough Cleanup & Safety Practices. You shouldn’t be finding nails in your driveway or garden beds months after the job is done.
How We Evaluated the Contractors on This List
To build this list, we evaluated companies based on verified Google reviews, years in business, range of services offered, responsiveness and professionalism, local reputation and community presence, transparency in communication, and specialization in products made for New England weather.
This list was created using the same criteria we’d use to guide a close friend or neighbor.
The Top 6 Roofing Contractors in Berkshire County, Massachusetts (Listed In Alphabetical Order)
| AC Wood Contracting, Inc. | |
|---|---|
|
Location |
Lanesborough, MA |
|
Years In Business |
15+ |
|
Specialties |
Asphalt shingles, EPDM flat roofing, dormers, skylights |
|
Known For |
GAF Master Elite® certification; strong customer communication |
|
Google Rating |
4.9 stars • 90+ reviews |
AC Wood Contracting is a Lanesborough-based contractor serving all of Berkshire County. They hold a GAF Master Elite® certification – a designation earned by fewer than 2% of roofing contractors in the country, which means they can offer GAF’s enhanced warranties on your roof. Customers praise their responsiveness, professionalism, and the quality of their crews.
Pros
- GAF Master Elite® certified, unlocking the highest-tier manufacturer warranties available
- Strong reputation for clear communication from estimate through completion
- Handles both residential and commercial projects across the county
Cons
- AC Wood is a full-service general contractor, meaning roofing is one of several service lines alongside excavation and trucking, not their sole focus
- Smaller team compared to larger regional competitors, which can affect scheduling during peak seasons
| Adam Quenneville Roofing & Siding | |
|---|---|
|
Locations |
Pittsfield, MA • South Hadley, MA • Manchester, CT |
|
Years In Business |
30+ |
|
Specialties |
Roof replacement, siding, gutter guards, roof cleaning and Rejuvenation |
|
Known For |
Regional presence across Western MA and the Berkshires; education-first approach |
|
Google Rating |
5.0 stars • 100+ reviews (Pittsfield) · 1,260+ reviews company-wide |
Adam Quenneville Roofing & Siding has been serving Western Massachusetts homeowners for over 30 years. With three locations, including our Pittsfield office that serves all of Berkshire County, we are one of the few roofing companies in the region with the team size, infrastructure, and local knowledge to handle both residential and commercial projects across the entire county. Our company-wide Google review count of 1,260+ is among the highest of any roofing contractor in the region.
Beyond roof replacement, we offer roof cleaning through our AQ MossBuster service, gutter guard installation, and siding, making us a full exterior partner for homeowners who want to work with one trusted company over time.
Pros
- Three locations, including Pittsfield, providing full Berkshire County coverage
- Large, experienced team enables fast turnaround and reliable scheduling
- One of the highest total review counts in the region
- Offers roof replacement, roof cleaning, gutter guards, and siding under one roof
- An education-first approach means you’ll understand exactly what we’re doing and why
Cons
- Because we prioritize thorough inspections and education, our process takes longer than “quick-quote” competitors, by design
- Homeowners looking for same-day emergency patch work from a single-person crew may be better served by a smaller local contractor
| Berkshire Roofing Co LLC | |
|---|---|
|
Location |
Stockbridge, MA |
|
Years In Business |
20+ (Founded 2002) |
|
Specialties |
Standing seam metal roofing, asphalt shingles, EPDM flat roofing, cedar shingles |
|
Known For |
High-end metal roofing; certified master installations |
|
Google Rating |
4.9 stars • 50+ reviews |
Founded in 2002 by Mike and Dorota Linde, Berkshire Roofing Co LLC has built a strong local reputation for premium roofing systems, particularly standing seam metal roofs, which are one of the most durable options available for New England winters. They hold a BBB A+ rating and carry certifications as a Master Installer for both Owens Corning and Drexel Metals standing seam panels.
Pros
- Certified Master Installer for Owens Corning and Drexel Metals, a strong indicator of technical expertise
- Standing seam metal roofing is an excellent long-term investment for Berkshire County homes
- Long-standing local reputation with a BBB A+ rating
Cons
- Fewer total Google reviews than some competitors, making it harder to assess patterns over time
- Premium materials and certifications typically come with a higher price point
| Chris Battaini Roofing & Seamless Gutters | |
|---|---|
|
Location |
Lee, MA |
|
Years In Business |
20+ |
|
Specialties |
Residential and commercial roofing, seamless gutters |
|
Known For |
Owner involvement on every job; strict clean-site guarantee |
|
Google Rating |
5.0 stars • 160+ reviews |
Chris Battaini Roofing is one of the most highly reviewed roofing contractors in Berkshire County, holding a perfect 5.0 rating across more than 160 Google reviews. What sets this company apart is owner Chris Battaini’s direct involvement on job sites. Customers frequently mention his hands-on presence, the crew’s professionalism, and the company’s “clean site guarantee”, a promise that your yard and walkways will be nail-free at the end of every workday. They also back their work with 15-to-50-year workmanship and material warranties.
Pros
- Perfect 5.0 Google rating with a strong, high-volume review history
- The owner is actively involved and often on-site throughout the project
- “Clean site guarantee” is a meaningful commitment, not just a marketing claim
Cons
- A smaller crew size may mean longer lead times during peak storm seasons
- Coverage is strongest in South and Central Berkshires; homeowners in Northern Berkshire County should confirm service availability
| J Smegal Roofing • Gutters • Repairs (Klaus Roofing Systems) | |
|---|---|
|
Location |
Lenox, MA (also South Hadley, MA) |
|
Years In Business |
15+ (since 2010) |
|
Specialties |
Roof replacement, roof repair, gutters, spray foam insulation |
|
Known For |
The “Klaus Roofing Way”; comprehensive property protection |
|
Google Rating |
4.9 stars • 270+ reviews |
Klaus Roofing Systems by J Smegal has been serving Berkshire County homeowners since 2010. With a Lenox office and a second location in South Hadley, they are positioned to serve both the Berkshires and the broader Western MA region. Their review volume is among the highest of any roofer in Berkshire County, and customers highlight their project management, communication, and attention to detail. They also offer spray foam insulation, an add-on for homeowners dealing with ice dams or energy efficiency issues.
Pros
- One of the highest review volumes of any Berkshire County roofer, with a 4.9 rating
- Comprehensive service offering that includes insulation and gutters alongside roofing
- Strong project management process with dedicated foremen on each job
Cons
- Being part of a larger branded network (Klaus Roofing Systems) may feel less personal to homeowners who prefer a small, owner-operated company
- Their large multi-county service area means scheduling can vary depending on demand
| R&T Roofing & Remodeling | |
|---|---|
|
Location |
Pittsfield, MA |
|
Years In Business |
10+ |
|
Specialties |
Residential and commercial roofing, siding, and windows |
|
Known For |
Fast turnaround; 0% financing options |
|
Google Rating |
4.8 stars • 80+ reviews |
R & T Roofing is a Pittsfield-based contractor that handles residential and commercial roofing alongside siding and window replacement. They offer 0% financing options, which can be a meaningful differentiator for homeowners managing a tight budget. Their crews are known for completing residential roofs quickly, often in a single day, and they operate seven days a week with emergency services available.
Pros
- 0% financing options make larger projects more accessible
- Fast turnaround, with many residential roofs completed in one day
- Full exterior services allow homeowners to bundle roofing, siding, and windows
Cons
- Some past reviews mention inconsistencies in communication and contract follow-through; worth asking specific questions before signing
- Manufacturer certifications are not prominently featured, so it’s worth asking about warranty coverage during your estimate
Comparing The Top Roofing Contracts: A Quick Overview
Now that you’ve had a chance to look at each company individually, here’s a quick side-by-side overview to make comparing them a little easier. This chart highlights each contractor’s years in business, specialties, and Google rating so you can quickly see how they stack up at a glance.
| Company | Years in Business | Specialties | Google Rating |
|---|---|---|---|
|
AC Wood Contracting Inc. |
15+ |
Asphalt shingle roofing, EPDM flat roofing, dormers, skylights |
4.9 |
|
Adam Quenneville Roofing & Siding |
30+ |
Roof replacement, siding, gutter and guards, roof cleaning, roof rejuvenation |
5.0 |
|
Berkshire Roofing Co LLC |
20+ |
Standing seam metal roofing, asphalt shingles, EPDM flat roofing, cedar shingles |
4.9 |
|
Chris Battaini Roofing |
20+ |
Residential roofing, commercial roofing, seamless gutters |
5.0 |
|
J Smegal Roofing |
15+ |
Roof replacement, roof repair, gutters, spray foam insulation |
4.9 |
|
R&T Roofing & Remodeling |
10+ |
Residential roofing, commercial roofing, siding, windows |
4.8 |
How to Avoid Roofing Scams in Berkshire County
Roofing scams spike after severe storms and the Berkshires see their share of them. Here’s how to protect yourself.
Red Flags to Watch For:
- Contractor asks for a large payment upfront before materials are delivered
- No physical address or verifiable local license
- High-pressure tactics (“This price is only good today”)
- Refuses to show proof of insurance or certifications
- Quote is significantly lower than all others you’ve received
Green Flags of a Reputable Roofer:
- Clear, written estimate with line items
- Proof of liability insurance and workers’ compensation
- Manufacturer certifications (GAF, Owens Corning, CertainTeed)
- Local references and a verifiable business address
- A Google review history spanning years, not months
- Willing to answer every question without pressure
Choosing the Right Roofer for Your Berkshire Home
The right roofing contractor isn’t only the one with the best price. It’s the one who gives you confidence, clarity, and long-term peace of mind.
We created this guide to help you compare trusted local roofing companies and choose the one that best fits your home, your budget, and your situation.
If that ends up being us, we’d be honored.
But even if you choose another reputable contractor from this list, you’ll still be in excellent hands.
Ready for a second opinion or want to compare quotes?
Request a free, no-pressure roof inspection from our team at Adam Quenneville Roofing & Siding. We serve all of Berkshire County from our Pittsfield location, with additional teams available from our South Hadley and Manchester, CT offices. We’re here to help you make the right decision, even if you don’t choose us.
