Missing a business tax deadline is one of the most avoidable and expensive mistakes a small business can make. The tricky part in our region is that you may answer to more than one government: the IRS, your state, and your city or county, each with its own dates. A business in Fairfax County, one in the City of Alexandria and one in DC do not follow the same calendar.

Here is a practical 2027 calendar for businesses in Northern Virginia, Maryland and Washington, DC. Dates that fall on a weekend or holiday generally move to the next business day, and in 2027 that applies to a few of these, which we flag below. Always confirm your own dates, because rules and deadlines change.

January and February

  • January 15: fourth-quarter 2026 federal estimated tax payment for owners and self-employed taxpayers.
  • February 1: Forms W-2 and 1099-NEC are due to recipients and to the IRS. The usual January 31 date falls on a Sunday in 2027. Remember that the 1099 reporting threshold is now $2,000 for payments made in 2026.

March

  • March 1: local business license (BPOL) renewals in the Virginia localities we work in, including Fairfax County, Arlington, the City of Alexandria, the City of Fairfax and the Town of Vienna. Filing and payment are generally due together, and late filing can bring a 10% penalty.
  • March 15: federal returns for calendar-year S corporations and partnerships (or an extension request).

April

  • April 15: federal returns for individuals and C corporations (or an extension), and first-quarter estimated tax payments.
  • April 15: Maryland annual report and business personal property return with the State Department of Assessments and Taxation for every Maryland business entity.
  • April 15: DC franchise tax returns for calendar-year corporations and unincorporated businesses.

May

  • May 1: business tangible personal property returns in Fairfax County, Arlington and the City of Alexandria (and for businesses in the Towns of Vienna, Herndon and Clifton, who file the property return with Fairfax County). May 1, 2027 falls on a Saturday, so confirm how your locality treats the date.

June through September

  • June 15: second-quarter federal estimated tax payment.
  • July 31: DC business personal property return. It is due every year even when no tax is owed, because DC excludes the first $225,000 of property value. July 31, 2027 is a Saturday.
  • September 5: Arlington business tangible property tax payment, after the May return.
  • September 15: third-quarter estimated tax payment, and the extended deadline for S corporation and partnership returns.

October through December

  • October 5: Fairfax County and City of Alexandria business property tax payments.
  • October 15: extended deadline for individual and C corporation returns.
  • Before December 31: the window for year-end tax planning, equipment purchases and retirement contributions. See our year-end tax planning checklist for what to do.

How the rules differ by location

The same calendar does not apply everywhere, so here is where the local rules split:

Map of the Washington, DC region with pins marking Northern Virginia, DC and Maryland locations

  • Fairfax County, including Reston and Tysons: the county business license is due March 1, the property return by May 1 and the payment by October 5. Learn more on our page for a CPA firm in Fairfax, VA and our guide for Reston, VA.
  • Town of Vienna: the business license is issued by the town, not the county, while the property return still goes to Fairfax County. Our Vienna, VA guide explains the difference.
  • Arlington: the license is due March 1, the property return by May 1, and the payment by September 5. See our guide for an Arlington, VA CPA firm.
  • City of Alexandria: an independent city with its own business tax office, and a rule that a business starting up after January 1 owes no business personal property tax for that year. See our Alexandria, VA guide.
  • Washington, DC: franchise tax, a July 31 property return and a Basic Business License that requires a Certificate of Clean Hands. See our Washington, DC guide.
  • Maryland: an April 15 annual report, county income tax collected on the state return, and an optional pass-through entity election. See our Bethesda, MD guide.

Tips for staying on top of the calendar

Two coworkers setting tax deadline reminders on a shared calendar

  1. Put every date on one shared calendar with a reminder at least two weeks ahead, not on the day.
  2. Know which jurisdiction you are in. A Vienna or Herndon mailing address does not always mean you are inside the town limits.
  3. Do not rely on a mailed form. Several localities mail renewals, but not receiving one does not excuse a late filing.
  4. Keep a fixed asset list. It supports your property tax returns and your federal depreciation.
  5. Ask for help early. Extensions often have to be requested before the deadline, not after.

If you want help keeping all of these straight, we handle business tax filings across Virginia, Maryland and DC as part of our accounting services. Get in touch or call (703) 865-4565.

This article is for general information only and is not tax, legal or accounting advice. Deadlines and rules change, and how they apply depends on your circumstances.