Year-End Tax Checklist for Cape Cod Business Owners

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Hard deadlineBest done early

October

November

December

January

01Look at the summer you actually hadDetailsNow

Look at the summer you actually had

Do this first, in October

Pull your profit and loss through September and compare it with last year. If the season ran well ahead of last year, your estimated payments were probably based on the smaller number, and it’s much easier to adjust now than to find out in April.

That review of your season is really the start of a bigger fall planning window. We’ve mapped out what to look at in our guide to Q4 tax planning for business owners. It’s a good companion to this checklist.

Year-to-date profit compared with the same point last year
Estimated tax payments made so far in 2026, federal and Massachusetts
Any one-time income this year, like the sale of equipment, property or a piece of the business

06Clean up the books before the year closesDetailsOct to Nov

Clean up the books before the year closes

October and November

A clean set of books is what makes every other item on this list possible. If your bookkeeping slipped during the season, and it usually does on the Cape, the off-season is the right time to catch it up.

Reconcile every bank and credit card account through September
Separate any personal expenses that ended up in the business accounts
Flag anything you’re not sure how to categorize so we can look at it together

04Retirement contributions, while there’s still time to set one upDetailsBy Nov

Look at retirement contributions while there’s still time to set one up

A conversation for October, not February

Some retirement plans have to be set up before December 31 to count for this year, and others can wait until you file. Which one fits depends on whether you have employees, how you’re structured and how much room you want.

Note what you’ve contributed so far this year
Tell us if you’ve added employees, since that changes which plans make sense
If you already have a plan, confirm the deadline for this year’s contribution

07Think about your structure for next yearDetailsNov to Dec

Think about your structure for next year

Model it before December

If your business has grown, the way it’s set up may not fit anymore. Changes like an S corporation election have their own deadlines and trade-offs, and they’re worth modeling with real numbers before you commit.

If you’re a contractor working for yourself, self-employment tax is often the part of the structure question that catches people off guard. We’ve written about the self-employment tax trap that Cape Cod contractors run into. It’s worth a read before you sit down to talk about next year.

Note any big changes planned for 2027, like hiring, a second location or bringing in a partner
Ask us whether your current structure still makes sense for where the business is heading

03Decide on equipmentDetailsDec 31

Decide on equipment before December 31

In service by December 31

Equipment, vehicles and tools generally have to be placed in service by December 31 to be depreciated on this year’s return. Buying something in December only helps this year if it’s actually delivered and in use before the new year.

List anything you were planning to buy in the first quarter anyway
Ask us how the purchase would be treated before you sign, not after
Keep the invoice and the date it was put to work

02Check your fourth-quarter estimated paymentDetailsDec 15 / Jan 15

Check your fourth-quarter estimated payment

Individuals: January 15, 2027. Mass. corporations: December 15

The last federal and Massachusetts estimated payments for individuals are due January 15, 2027. If you run a corporation, the Massachusetts fourth-quarter payment lands earlier, on December 15.

Recalculate the Q4 payment using this year’s actual numbers, not last April’s guess
If you’re an S corporation owner, confirm your salary and distributions still make sense for the year
If income jumped this year, ask us whether the Massachusetts 4% surtax is in play (for 2026 it applies to taxable income over $1,107,750)

05Payroll and contractor records ready for JanuaryDetailsFeb 1

Get payroll and contractor records ready for January

W-2s and 1099-NECs due Monday, February 1, 2027

W-2s and 1099-NECs are due at the end of January. In 2027 that deadline is Monday, February 1, because January 31 falls on a Sunday. The weeks after the holidays go quickly, and chasing a contractor’s W-9 in mid-January is nobody’s favorite project.

Collect a W-9 from every contractor you paid this year
Confirm addresses and Social Security numbers for seasonal staff who have already left
Review anyone you paid as a contractor who worked like an employee, because Massachusetts takes a strict view of that line

Let’s go through it together

Every business is different, and tax rules change often enough that a checklist can only get you started. If you’d like us to go through your year-end numbers with you, book a time and we’ll look at where you stand while there’s still room to act.

Book a time with our teamTax laws change frequently. This checklist is for general informational purposes. Talk with a tax professional about your specific situation.

The Cape Cod Business Owner’s Year-End Tax Checklist

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