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TRUSTED BY CHESHIRE, MA HOMEOWNERS

  • Average homeowner rating star icon4.6
    Average homeowner rating
  • Verified reviews icon150
    Verified tree services reviews

Verified Reviews for Tree Service pros in Cheshire, MA

*The Angi rating for Tree Service companies in Cheshire, MA is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Tree Service needs.

*The HomeAdvisor rating for Tree Service companies in Cheshire, MA is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Tree Service needs.

Last update on January 21, 2026

Find Tree service pros in Cheshire

Avatar for Day and Sons Enterprises LLC

Day and Sons Enterprises LLC

5.00(
8
)
•Approved Pro

Day and Sons Enterprises LLC

5.00(
8
)
•Approved Pro
Customers say: Quick response
5 years of experience
Free onsite estimate

Day and Sons Enterprises LLC has 20 years experience in landscaping. We are a veteran owned & operated business serving the Capital District of New York. Whether its hardscaping, landscaping, hydroseeding, excavation or snow removal we are the company that will provide you with professional service.

"Ryan has provided top-notch service in taking care of my mother-in-law‘s house – mowing, trimming, plowing, etc., and has always been attentive and responding to any requests. I highly recommend this service."

Robert R on January 2026

Day and Sons Enterprises LLC has 20 years experience in landscaping. We are a veteran owned & operated business serving the Capital District of New York. Whether its hardscaping, landscaping, hydroseeding, excavation or snow removal we are the company that will provide you with professional service.

"Ryan has provided top-notch service in taking care of my mother-in-law‘s house – mowing, trimming, plowing, etc., and has always been attentive and responding to any requests. I highly recommend this service."

Robert R on January 2026

Avatar for Aligned Design Landscaping, LLC

Aligned Design Landscaping, LLC

4.94(
8
)
•Approved Pro

Aligned Design Landscaping, LLC

4.94(
8
)
•Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
3 years of experience

Aligned Design Landscaping is a fully insured LLC based in Berkshire County, Massachusetts. Co-owners Eliot James DeLeo and Lucas Deambrogio have over 15 years of landscaping experience combined. The Berkshire natives specialize in landscape design, tree & plant installation, mulching, trimming, patio/stone work, as well as spring & fall cleanups. Aligned Design Landscaping prides themselves on top-tier quality, efficiency, attention to detail, customer satisfaction, and integrity. Servicing both residential and commercial properties, Aligned Design’s goal is to keep the Berkshires beautiful, one landscape at a time!

"ð good job"

Charles P on November 2023

Aligned Design Landscaping is a fully insured LLC based in Berkshire County, Massachusetts. Co-owners Eliot James DeLeo and Lucas Deambrogio have over 15 years of landscaping experience combined. The Berkshire natives specialize in landscape design, tree & plant installation, mulching, trimming, patio/stone work, as well as spring & fall cleanups. Aligned Design Landscaping prides themselves on top-tier quality, efficiency, attention to detail, customer satisfaction, and integrity. Servicing both residential and commercial properties, Aligned Design’s goal is to keep the Berkshires beautiful, one landscape at a time!

"ð good job"

Charles P on November 2023

Pittsfield Handyman

4.17(
3
)
•Approved Pro

Pittsfield Handyman

4.17(
3
)
•Approved Pro
Customers say: Quality work
11 years of experience

Hi. My name is Liz, and together with my husband, Luis, his son Marcelo, and his nephew Renato, we are Berkshire Handyman. We are in Pittsfield and we serve central Berkshire County. We do what we say and we say what we will do. We don’t make promises we can’t deliver on. We’re not the cheapest. But, personally, I think we are the best. (We’re also really nice.)

"Prompt and courteous. Worked through completion."

Matt C on January 2023

Hi. My name is Liz, and together with my husband, Luis, his son Marcelo, and his nephew Renato, we are Berkshire Handyman. We are in Pittsfield and we serve central Berkshire County. We do what we say and we say what we will do. We don’t make promises we can’t deliver on. We’re not the cheapest. But, personally, I think we are the best. (We’re also really nice.)

"Prompt and courteous. Worked through completion."

Matt C on January 2023

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
6 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

Avatar for My Computer Works

My Computer Works

4.61(
231
)

My Computer Works

4.61(
231
)
Customers say: Quality work
21 years of experience

When your P.C. , Tablet or Cell Phone has you stumped you need an American based tech team on speed dial: Call Now: 877-378-9258. Remote, online, and in home support from the good old USA. In need of a performance improving tune-up? Have a virus or spyware issue? We have you covered. Have questions about a program, your printer, importing photos, working with websites, working with your computer, or just needing advice on what to buy? My Computer Works membership gives you go to access to the IT support you need, a data-back up solution second to none, and training all in one place.

"Went very well :)"

Margie H on June 2022

When your P.C. , Tablet or Cell Phone has you stumped you need an American based tech team on speed dial: Call Now: 877-378-9258. Remote, online, and in home support from the good old USA. In need of a performance improving tune-up? Have a virus or spyware issue? We have you covered. Have questions about a program, your printer, importing photos, working with websites, working with your computer, or just needing advice on what to buy? My Computer Works membership gives you go to access to the IT support you need, a data-back up solution second to none, and training all in one place.

"Went very well :)"

Margie H on June 2022

Avatar for Pridemark Tree Services LLC

Pridemark Tree Services LLC

4.79(
19
)

Pridemark Tree Services LLC

4.79(
19
)
Customers say: Super punctual
Recommended by 94% of Angi customers
Recommended by 94% of HomeAdvisor customers

We specialize in Tree Removal, Tree Trimming, Stump Grinding, Brush Clearing, Land Clearing, Tree Pruning, Hedge Trimming, and Gutter Cleaning. When necessary, we remove large or dangerous trees using a crane or a bucket truck. We also use technical rigging and climbing. In addition, during the winter, we can clear ice dams and snow from roofs/decks/etc.

"Steve and his team were great from beginning to the end. Steve worked me into his schedule as I had a fast approaching deadline, many other companies wouldn't even call back or even consider trying to get me in earlier in there schedule. I had a 80-90 foot pine tree between 2 houses, a garage, and a vinyl fence possibly the most worrisome case for most home owners. When Steve came and gave the estimate, he walked me through where his crane was going to be placed with its outriggers and how the removal was going to be performed. When it came to the removal, his crew was clean cut, professional and organized. They removed the tree without incident, and when they left you would have had no idea they were just there with a crew, equipment and a 135 foot crane. To me the price didn't matter since Steve took such great care of the removal, I could probably have had it removed a little cheaper but how smooth the transaction was with Pridemark I had no issue at all paying what I paid. Also all day I had neighbors coming over saying they watched the whole removal and were blown away by how great of a job Pridemark did. They will be the ones I call for all my tree issues and the only tree removal contact I now have saved in my phone."

Tanner B on May 2020

We specialize in Tree Removal, Tree Trimming, Stump Grinding, Brush Clearing, Land Clearing, Tree Pruning, Hedge Trimming, and Gutter Cleaning. When necessary, we remove large or dangerous trees using a crane or a bucket truck. We also use technical rigging and climbing. In addition, during the winter, we can clear ice dams and snow from roofs/decks/etc.

"Steve and his team were great from beginning to the end. Steve worked me into his schedule as I had a fast approaching deadline, many other companies wouldn't even call back or even consider trying to get me in earlier in there schedule. I had a 80-90 foot pine tree between 2 houses, a garage, and a vinyl fence possibly the most worrisome case for most home owners. When Steve came and gave the estimate, he walked me through where his crane was going to be placed with its outriggers and how the removal was going to be performed. When it came to the removal, his crew was clean cut, professional and organized. They removed the tree without incident, and when they left you would have had no idea they were just there with a crew, equipment and a 135 foot crane. To me the price didn't matter since Steve took such great care of the removal, I could probably have had it removed a little cheaper but how smooth the transaction was with Pridemark I had no issue at all paying what I paid. Also all day I had neighbors coming over saying they watched the whole removal and were blown away by how great of a job Pridemark did. They will be the ones I call for all my tree issues and the only tree removal contact I now have saved in my phone."

Tanner B on May 2020

Avatar for Beaver Tree Works

Beaver Tree Works

4.93(
14
)

Beaver Tree Works

4.93(
14
)
Customers say: Quick response
Recommended by 92% of Angi customers
Recommended by 92% of HomeAdvisor customers

Don't trust your trees to just anyone. The quality of your tree removal job may be measured by what you don't see after it is done! We protect your beautiful greenscape and property and leave it as nice or better than when we arrived.

Don't trust your trees to just anyone. The quality of your tree removal job may be measured by what you don't see after it is done! We protect your beautiful greenscape and property and leave it as nice or better than when we arrived.

Avatar for Hugh's Tree Svc

Hugh's Tree Svc

5.00(
7
)

Hugh's Tree Svc

5.00(
7
)
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers

Hugh's Tree service specializes in tree removal, pruning, storm damage & snow removal. We strive on giving our customers the fairest prices.

Hugh's Tree service specializes in tree removal, pruning, storm damage & snow removal. We strive on giving our customers the fairest prices.

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Tree Service questions, answered by experts

An arborist specializes in tree care, performing tasks such as pruning, treating diseases, and removing hazardous trees. They also assess soil conditions, plant trees, and develop landscaping plans to ensure healthy growth. They also manage debris cleanup, inspect equipment, and record maintenance activities. Arborists often collaborate with landscapers and professional tree maintenance services, applying their specialized knowledge and problem-solving skills to maintain tree health and safety.

Pruning a tree is a yearly DIY job that involves removing small dead branches, leaves, and blooms to help the tree grow bigger and stronger. You can often complete the job with basic home gardening tools. Trimming a tree, however, removes larger sections to control the direction the tree grows in and protects your home, utility wires, and yard from potentially dangerous branches.

Yes, you should trim the lower branches of your maple tree for safety. Trimming maple trees as they grow helps lift the crown and canopy and trains it to grow straight up. A good rule of thumb is to prune enough branches to leave 6 feet of clearance under the 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.

Finding a reliable arborist starts with researching specialists in your area and checking their licensing and certifications. Use online resources like the Better Business Bureau (BBB) to conduct research on each company. Next, contact the arborist and ask the following questions to see whether they are the right fit for your project:

  • Do you handle or specialize in dealing with the issue I’m having?

  • Are you fully insured?

  • Do you have customer references I can call?

  • Do you have any third-party certifications?

  • What equipment and strategies do you plan to use?

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.

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