Tree Service in Chestertown, MD

Chestertown is about 20 miles north of our yard in Queenstown. Our trucks come up MD 213 through Centreville, pass through Kingstown and cross the Chester River bridge right into town. We work on the brick homes of the historic district, the waterfront along Water Street, the streets around Washington College and the newer neighborhoods at the edge of town. Old, tall shade trees on small lots are a big part of the work here. Our crews are led by a Maryland Licensed Tree Expert (LTE# 1929), and we answer storm calls 24/7.

Here’s How It Works

Get in touch today to learn more about us and our services. We’ll provide you with a free estimate to help you make the right decision for your project and your budget.

Let us do the work. Our expert team will arrive on time at your Chestertown, Maryland, home or business and will quickly, safely, and effectively remove the specified tree(s).

After we’ve finished removing the trees/branches, etc., we will thoroughly clean the work area and remove all debris, leaving your property neat and tidy.

Big Trees in a Historic River Town

Chestertown is the Kent County seat, and its historic district is full of older homes with trees to match. Large oaks and maples grow close to porches, chimneys, slate roofs and brick walks. Taking one down usually means climbing it and lowering it in sections instead of dropping it whole.


The town looks after its trees. Chestertown is a Tree City USA community with its own tree committee, and the town may require a permit and a licensed tree expert’s report before a larger tree on private property is removed. Street and park trees are covered by town rules as well. We check what the town needs before any work starts and provide the LTE documentation.


Lots along the Chester River and Radcliffe Creek are also in the Chesapeake Bay Critical Area. Inside town limits, Chestertown runs its own Critical Area program, so approvals go through Town Hall rather than Kent County. We can help you sort out which rules apply to your yard and what replanting, if any, will be needed.

Worker in a bucket lift trimming tree branches beside power lines under a blue sky

When the Chester River Rises and Trees Come Down

Chestertown’s waterfront sits low along the Chester River. During Hurricane Isabel in September 2003, tidal flooding reached into Chestertown and pushed inland along the river, while the record tide upriver at Tolchester Beach reached 7.91 feet. Even ordinary high tides can flood the lowest streets near the river. Wet ground loosens roots, and a strong wind can then lay a big tree across a roof, car or street. If that happens at your place, call 410-827-5198 any time, day or night. We run 24/7 and will make the scene safe.

Person cutting a large tree trunk with a chainsaw in a yard, sawdust flying.
Worker using a stump grinder to remove a tree stump beside a sidewalk

Common tree problems in Chestertown:

Trees crowding old houses. Many historic homes have shade trees just a few feet from the walls. Limbs rub roofs and gutters, and roots push against old foundations. Careful pruning or a sectional removal protects the house and the yard.

Soggy ground near the water. Yards near the Chester River and Radcliffe Creek stay wet much of the year. Trees there grow shallow roots, which makes them more likely to tip over in a storm when the soil is saturated.

Ash trees in decline. Emerald ash borer was confirmed in Kent County in 2017. Ash trees in town yards and along streets can die within a few years of infestation, and a dead ash is brittle and unpredictable to take down.

Roots under brick walks. Big street and yard trees can lift brick sidewalks, patios and driveways as their roots grow. We can trim, assess or remove the tree and grind the stump so the area can be repaired.


Our Chestertown customers count on us for tree removal on tight lots, trimming and pruning of mature shade trees, stump grinding and storm damage cleanup. Riverfront owners can also hire us for Marsh Master phragmite control, and anyone can order seasoned firewood. We are permitted to move and sell wood under Maryland rules. Ask for a free estimate and we will come take a look.

Neighborhoods and Nearby Towns We Serve

We work all over Chestertown, from the historic district and the Water Street waterfront to the Washington College area, Radcliffe Creek and the newer homes on the edge of town. Close by, we serve Kingstown just across the Chester River bridge in Queen Anne’s County, plus Fairlee, Georgetown, Worton, Butlertown, Langford and Lynch. See our Kent County tree service page, or visit our pages for Rock Hall and Centreville.


Chestertown Tree Service FAQ

Do I need a permit to remove a tree in Chestertown?
Possibly. Chestertown may require a town permit and a licensed tree expert’s review before a larger tree on private property comes down, and street trees fall under town rules. Small trees and routine pruning are usually simpler. We check with the town before we start, so you are not caught off guard.


Who approves tree work on my riverfront lot in town?
Inside Chestertown limits, the town handles the Chesapeake Bay Critical Area program, so approvals for trees near the Chester River or Radcliffe Creek go through Town Hall. Just outside town, Kent County handles them. We can tell you which office applies to your address.


Do you also work in Kingstown?
Yes. Kingstown is right across the Chester River bridge in Queen Anne’s County, and it is on our way to Chestertown from Queenstown. Waterfront lots there fall under Queen Anne’s County’s Critical Area permit rules, which we work with regularly.


Can you take down a big tree on a small downtown lot?
Yes. When there is no room to fell a tree, our climbers take it apart from the top down and lower each piece by rope, away from roofs, fences and neighbors. We clean up the debris and can grind the stump the same visit.

Schedule tree service in Chestertown today!