The Maryland Small Business
Annual Calendar

Running a Maryland business means a steady rhythm of filings, payments, and renewals across the year. This calendar walks through the deadlines and opportunity windows that matter for most small businesses — federal and Maryland-specific — so nothing sneaks up on you.

A note on accuracy: Tax dates and SDAT fees can change. Treat this as a planning calendar and verify the specifics against Maryland SDAT, the Maryland Comptroller, the IRS, and FinCEN (for BOI) before relying on a specific date or fee for your filing.

January

• Jan 15 — Q4 prior-year federal and Maryland estimated tax payment due (Form 1040-ES; MD Form 502D).
• Jan 31 — W-2s due to employees and to the Social Security Administration; 1099-NEC due to non-employee contractors and to the IRS.
• Jan 31 — Q4 Maryland Unemployment Insurance return and payment due.
• Watch for: Many TEDCO programs reopen application windows at the start of the calendar year.

February

• Mid-month — Workers’ comp policy audits commonly land here; respond promptly to avoid premium adjustments.
• Feb 28 — Paper 1099 filings to the IRS due (electronic filers have until Mar 31).

March

• Mar 15 — S-corporation (Form 1120-S) and partnership (Form 1065) federal returns due. K-1s out to owners.
• Mar 15 — Maryland pass-through entity return (Form 510) due.
• Watch for: Start SDAT annual report prep — pull last year’s asset list for the personal property return.

April — The Big One

• Apr 15 — Federal individual return (Form 1040) and C-corp return (Form 1120) due. Six-month extension to Oct 15 available.
• Apr 15 — Maryland individual income tax (Form 502) due.
• Apr 15 — Q1 federal and Maryland estimated tax payment due.
• Apr 15 — SDAT Annual Report and Personal Property Return due for most domestic entities (LLC, Corp, LP, LLP). The standard filing fee for most for-profit entities has long been $300 — confirm current fee on the SDAT site.
• Apr 30 — Q1 Maryland UI return and payment due.

May

• Quiet month for filings — use it to catch up on bookkeeping, plan summer hiring, and review pricing for the second half of the year.
• Watch for: County small-business loan and grant rounds often open in late spring.

June

• Jun 15 — Q2 federal and Maryland estimated tax payment due.
• Jun 30 — Mid-year close opportunity. Trial-balance your books, look at gross margin, and update your 13-week cash forecast.

July

• Jul 31 — Q2 Maryland UI return and payment due.
• Jul 31 — Form 5500 (qualified retirement plan return) typically due for calendar-year plans.
• Watch for: EARN Maryland workforce training grants generally run on the state fiscal year (Jul–Jun), so funding cycles often refresh in July.

August

• Quiet month — a good window to draft a year-end tax plan with your CPA and review benefits decisions before fall open enrollment.

September

• Sep 15 — Q3 federal and Maryland estimated tax payment due.
• Sep 15 — Extended S-corp and partnership returns due (for those who filed extensions in March).

October

• Oct 15 — Extended individual (Form 1040) and C-corp (Form 1120) returns due.
• Oct 31 — Q3 Maryland UI return and payment due.
• Watch for: Year-end planning territory — bonuses, Section 179 / bonus depreciation purchases, retirement contributions, charitable giving.

November

• Open enrollment — Most group health insurance renewals land here.
• Watch for: Begin collecting W-9s from contractors so January 1099s aren’t a scramble.

December

• Dec 31 — Final date for most year-end tax moves: equipment placed in service, retirement contributions for the year, charitable donations.
• Dec 31 — Last chance to collect W-9s from contractors paid in the current year.
• Watch for: SDAT typically begins accepting next year’s annual reports in early January — filing in the first weeks of the year avoids the April rush.

Year-round watch list

• Maryland Sales & Use Tax — Returns generally due the 20th of the month following the period covered (most filers are monthly; lower-volume filers may be quarterly or annual). File through the Maryland Comptroller’s online system.
• Local business licenses — Renewal cadence varies by county and city. Check with your county clerk; many counties operate on a fiscal-year cycle.
• Trader’s license — Required in many Maryland counties for businesses selling tangible goods. Renewals are typically annual.
• BOI (Beneficial Ownership Information) reporting — Reporting under the Corporate Transparency Act has shifted multiple times due to court action. Verify current FinCEN requirements before assuming a deadline applies to you.
• Workers’ compensation — Annual policy renewal with an audit at year-end; budget for premium true-ups.

Maryland small-business funding cycles

Funding doesn’t follow a tax-style calendar, but a few patterns repeat:

• TEDCO — Multiple programs with rolling and quarterly windows. Check the TEDCO portal at the start of each quarter.
• MSBDFA — Maryland Small Business Development Financing Authority; rolling intake, but funding decisions tend to cluster in the middle of the year.
• EARN Maryland — Workforce training grants generally cycle with the state fiscal year (Jul–Jun).
• County funds — Many counties run small-business loan or grant programs that open in spring and fall. Watch your county’s economic development page.

Bookmark worth making: SDAT, Maryland Comptroller, and the FinCEN BOI portal. Verify specifics on the source before relying on them for your filing.