Top-rated tree service pros.

Get matched with top tree service pros in Cheshire, MA

Enter your ZIP and get matched with up to 5 pros

Need a pro for your tree service project in Cheshire, MA?

Select your specific project to find the pro for you.

TRUSTED BY CHESHIRE, MA HOMEOWNERS

  • Average homeowner rating star icon4.7
    Average homeowner rating
  • Verified reviews icon148
    Verified tree services reviews

Find Tree service pros in Cheshire

Casey's Tree Service

5.00(
2
)
Approved Pro

Casey's Tree Service

5.00(
2
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
5 years of experience

Casey's Tree Service is dedicated to providing our customers with the best quality and craftsmanship. We are here to build relationships with our customers and communities and to provide our employees with a great place to work. We look forward to working with you!

"We had a rather large pine tree lake front obstructing our view We did not want to remove it but just wanted it professionally trimmed back. Casey did an excellent job. Now we have great, clear views of the waterfront. He showed up on time, was very professional and cleaned up the entire area."

Deborah F on January 2024

Casey's Tree Service is dedicated to providing our customers with the best quality and craftsmanship. We are here to build relationships with our customers and communities and to provide our employees with a great place to work. We look forward to working with you!

"We had a rather large pine tree lake front obstructing our view We did not want to remove it but just wanted it professionally trimmed back. Casey did an excellent job. Now we have great, clear views of the waterfront. He showed up on time, was very professional and cleaned up the entire area."

Deborah F on January 2024


"Really great job "

John L on November 2025

We are committed to delivering exceptional work at competitive and reasonable prices, which has earned us the trust of our community. We invite you to contact us for a complimentary quote.

"Really great job "

John L on November 2025


Stump Wrecker

No reviews yet

Stump Wrecker

No reviews yet
Emergency services offered

Professional Stump Grinding and Stump Removal Service. We are proud to be the Capital Regions number one Stump Grinding Service. Free Estimates and Fully Insured.

Professional Stump Grinding and Stump Removal Service. We are proud to be the Capital Regions number one Stump Grinding Service. Free Estimates and Fully Insured.


Avatar for K browns Property Maintenance

K browns Property Maintenance

No reviews yet

K browns Property Maintenance

No reviews yet
Free onsite estimate

K Browns Property maintenence is a locally owned and operated Company in Berkshire County with reliable pricing my areas I cover is and services I offer Handy men work 14 year experience Snow plowing Snow blowing 10 year experience furniture assembly 3 year expensive Any work that you need done around house I am will to help fully licensed and insured Give me call at 413-841-7736 to discuss further on details of stuff you would like done as always stay safe stay blessed and have a great day Richmond ma Pittsfield ma Lanasbroro ma Chesher ma Adams ma And more Depending on job North adams ma

K Browns Property maintenence is a locally owned and operated Company in Berkshire County with reliable pricing my areas I cover is and services I offer Handy men work 14 year experience Snow plowing Snow blowing 10 year experience furniture assembly 3 year expensive Any work that you need done around house I am will to help fully licensed and insured Give me call at 413-841-7736 to discuss further on details of stuff you would like done as always stay safe stay blessed and have a great day Richmond ma Pittsfield ma Lanasbroro ma Chesher ma Adams ma And more Depending on job North adams ma


"Nick was recommended to me by a family member who recently had their lawn hydroseeded by Coyne Brothers. They were professional, informative, and here when they said they would be! I too would recommend their services."

Chelsea B on August 2023

Family owned business with over 9 years of experience for residential and commercial Landscaping, Hydroseeding, light Excavation, Lawn and Yard work, mulch, bed maintenance.

"Nick was recommended to me by a family member who recently had their lawn hydroseeded by Coyne Brothers. They were professional, informative, and here when they said they would be! I too would recommend their services."

Chelsea B on August 2023


Eco Forestry and land management

No reviews yet

Eco Forestry and land management

No reviews yet
10 years of experience

We are a forestry mulching and land management company proudly serving New Hampshire, Vermont, & Maine We have a wide range of top of the line, cutting edge heavy equipment to help you with your projects. We treat every project equally, with our famously high standard of workmanship. Projects large or small, get it done right the first time! We are licensed & fully Insured.

We are a forestry mulching and land management company proudly serving New Hampshire, Vermont, & Maine We have a wide range of top of the line, cutting edge heavy equipment to help you with your projects. We treat every project equally, with our famously high standard of workmanship. Projects large or small, get it done right the first time! We are licensed & fully Insured.



Berkshire Property Rehab

No reviews yet

Berkshire Property Rehab

No reviews yet

Landscaping Tree Trimming Planting (Trees, Shrubs, Flowers, etc.) Ornamental Stonework Clearing Overgrowth Power Washing We can power wash anything from houses to driveways and everything in between. Clean Outs Whether you inherited a property or bought a house full of stuff you don't want or need, we can take care of most residential and commercial clean-outs for you. Mold Removal Do you have a mold issue that needs to be addressed? We can help identify the source and remove any affected materials. Property Renovation Consulting Do you need help with a plan to better utilize and add value to your property? Let us design a perfect layout for any budget. Floating Floor Installation Do you need an affordable way to upgrade your property? Floating floors come in a variety of styles and colors to fit your needs perfectly.

Landscaping Tree Trimming Planting (Trees, Shrubs, Flowers, etc.) Ornamental Stonework Clearing Overgrowth Power Washing We can power wash anything from houses to driveways and everything in between. Clean Outs Whether you inherited a property or bought a house full of stuff you don't want or need, we can take care of most residential and commercial clean-outs for you. Mold Removal Do you have a mold issue that needs to be addressed? We can help identify the source and remove any affected materials. Property Renovation Consulting Do you need help with a plan to better utilize and add value to your property? Let us design a perfect layout for any budget. Floating Floor Installation Do you need an affordable way to upgrade your property? Floating floors come in a variety of styles and colors to fit your needs perfectly.


Diggin It LLC

No reviews yet

Diggin It LLC

No reviews yet
Emergency services offered

We are a small owner-operated excavation company established in july of 2021 out of Westfield, MA. We offer a wide range of affordable services from excavation to retaining walls and everything in between. Licensed and insured.

We are a small owner-operated excavation company established in july of 2021 out of Westfield, MA. We offer a wide range of affordable services from excavation to retaining walls and everything in between. Licensed and insured.


Dylan's Landscaping & Handyman Services

No reviews yet

Dylan's Landscaping & Handyman Services

No reviews yet
4 years of experience

Here at Dylan's Landscaping & Handyman Services we offer alot from landscaping to tree work and removal (including brush) spring/fall clean-ups. We also do small repair jobs aswell, something broke and/or needs fixing? Dylan's Landscaping & Handyman Services can come out and fix it! A little about me, My name is Dylan and I am the proud Owner of Dylan's Landscaping & Handyman services. I just started up my business in the spring of 2021. I am a local to the Berkshires, i was born and raised here so i know my way around. I strive to do the best work. Some people seem to think i can be a perfectionist at times because of how long a project might take me just to make it look that much better. There's just no good quality in your work when you rush to get something done.

Here at Dylan's Landscaping & Handyman Services we offer alot from landscaping to tree work and removal (including brush) spring/fall clean-ups. We also do small repair jobs aswell, something broke and/or needs fixing? Dylan's Landscaping & Handyman Services can come out and fix it! A little about me, My name is Dylan and I am the proud Owner of Dylan's Landscaping & Handyman services. I just started up my business in the spring of 2021. I am a local to the Berkshires, i was born and raised here so i know my way around. I strive to do the best work. Some people seem to think i can be a perfectionist at times because of how long a project might take me just to make it look that much better. There's just no good quality in your work when you rush to get something done.

Showing 1-10 of 49
Tree Service questions, answered by experts

Many species, especially when well-established, are not fans of transplantation. You’ll need to decide if you want to risk splashing the cash, understanding that transplantation isn’t always successful. Again, this is where hiring a pro is helpful, as they can give you all the essential info you need to ensure your tree stands a fighting chance.

In most cases, leaving tree roots underground is not a problem if the stump has been removed or ground below the soil. However, some larger roots may decompose, leaving dents in your soil. Additionally, some aggressive trees, including willows, oaks, elms, maples, and poplars may grow back from roots. Large aggressive trees with established root systems are more likely to grow back.

No. Most of the time, suckers are only a sign that the tree is experiencing stress. However, they can also be the canary in the coal mine, letting you know that something else is stressing your tree. If you have lots of suckers on your tree, calling in an arborist or a tree care expert is always a good call to determine the cause and develop a solution that de-stresses your tree.

Generally, you should prune around 20% of an apple tree’s growth—and never more than 30%. This means that if you have a severely overgrown tree, it can take a few seasons to prune it back enough to produce the healthiest fruit. 

If you’re dealing with a newly planted or juvenile tree, hold off on pruning beyond the initial shaping. Wait at least a couple of seasons into fruit production since pruning can increase the number of water sprouts and unproductive foliage.

Yes, tree roots can regenerate after they’re pruned or cut. In fact, trimming can stimulate new growth, especially in healthy trees. The tree’s roots can still grow back even after a tree is cut down, (and learning how to get rid of regrowing tree roots is a separate feat). Still, if you don’t wish to harm a tree, pruning the roots should be done with extreme care, and ideally by a professional.

The Cheshire, MA homeowners’ guide to tree services

From average costs to expert advice, get all the answers you need to get your job done.

What do you need done? We’ll find top pros.
  • 🌱 "Mow a small front yard"
  • 🛠 "Fix a leaking pipe under the sink"
  • 🏠 "Repair shingles on an asphalt roof"