The best-rated tree services serving Pittsfield, MA, independently researched and ranked on rating, review volume and genuine local reputation.
The best tree services in Pittsfield, MA are Kelley Brothers Tree Service, Kevin Holden Tree Trimming & Removal, Northern Oak Tree & Home Services, Berkshire Tree Service and Woodchuck Tree Service. Each is an independently researched local operator, ranked on reputation, reviews and genuine local presence, and none paid to appear.
One business can feature above the Top 5 on this page, clearly labeled. A great way for a newer or smaller pro to get seen first.
Kelley Brothers Tree Service is a family-owned Pittsfield tree company that has built a strong local following over more than a decade in the Berkshires. The team is fully licensed and insured, keeps a Certified Tree Care Safety Professional on staff and belongs to the Tree Care Industry Association, handling everything from crane and lot clearing to stump grinding, forestry mulching and emergency storm work. Named a 'Best of the Berkshires' winner several years running, they carry one of the most respected reputations among local homeowners.
Kevin Holden Tree Trimming & Removal is a family-run tree care firm based in Richmond, just west of Pittsfield, where owners Kevin and Benn are on site for every job. Fully insured and guided by ISA arboriculture standards, they cover the whole of Berkshire County with pruning, removals, cabling and bracing, stump grinding and crane-assisted work. Their hands-on, owner-present approach has earned them a dependable name across the central Berkshires.
Northern Oak has served Pittsfield and the surrounding Berkshire towns since 2000, pairing tree work with land clearing and broader property services. From its Pittsfield base the crew handles tree removal, trimming, debris cleanup and lot clearing across Adams, Dalton, Lenox, Great Barrington and the wider county, with round-the-clock emergency response. Long established and locally rooted, they are a practical choice for homeowners wanting one accountable local contractor.
Berkshire Tree Service is a family-owned operation with more than three decades of tree care experience across the Berkshires. Working out of the Pittsfield area, they take on tree removal, land clearing, stump grinding, storm-damage cleanup and related landscaping, and offer 24-hour emergency service for fallen and hazardous trees. Their long tenure in the region has made them a familiar name for local property owners.
Run by Tim Hamilton, Woodchuck Tree Service is a family-owned, fully insured tree company serving Pittsfield and the wider Berkshires from nearby West Stockbridge. The crew covers everyday tree removal and trimming through to larger jobs across the county, and has built a solid word-of-mouth reputation among Berkshire homeowners. As a small owner-run outfit, they suit people who prefer dealing directly with the person doing the work.
The best tree services serving Pittsfield, MA are based in and around Pittsfield, Richmond and West Stockbridge. With the Northeast's four seasons and older housing stock to contend with, trees can grow fast and quickly become a hazard, so a proven local pro makes all the difference, and we've done the legwork to surface only the operators worth calling.
Kelley Brothers Tree Service currently tops the list, but every business here earns its place the same way: we research each tree service genuinely operating near Pittsfield, weigh real customer reviews and ratings from sources like Google and the Better Business Bureau, and rank on merit. No business can pay into this list, the single featured spot above it is the only paid placement, and it's always clearly labeled.
| Business | Best for |
|---|---|
| 1. Kelley Brothers Tree Service | Consistent, top-reviewed service |
| 2. Kevin Holden Tree Trimming & Removal | Fast response and repairs |
| 3. Northern Oak Tree & Home Services | Professional workmanship |
| 4. Berkshire Tree Service | Dependable service and value |
| 5. Woodchuck Tree Service | Everyday, all-round jobs |
Our current top picks are Kelley Brothers Tree Service, Kevin Holden Tree Trimming & Removal, Northern Oak Tree & Home Services, Berkshire Tree Service and Woodchuck Tree Service. Every business is independently researched and ranked on merit, never paid placement.
We research every tree service genuinely operating in and around Pittsfield, then weigh real customer reviews and ratings from sources like Google and the Better Business Bureau, review volume, and a genuine local track record. No business can pay to appear in the ranked Top 5.
No. The ranked Top 5 is editorial and cannot be bought. The only paid option is the single featured spot above the list, which is always clearly labeled as featured.
Start with the five above, then get written quotes from two or three, read their most recent reviews, and confirm they cover your part of Pittsfield. A good tree service responds promptly, explains the work clearly, and is upfront about pricing.
We rank on independent reputation and reviews, not licensing checks. Requirements vary by state and trade, so always confirm a pro's current license and insurance directly with them before any work begins.
Own the featured spot above this Top 5, clearly labeled. A great way for a newer or smaller pro to get seen first. Early-adopter rate $19/month for your first 6 months, then $39/month.