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Our Maryland small business tax calendar will hopefully help new and small business owners know when taxes are coming up and stay on top of their finances.
Running a business in Maryland means juggling clients, cash flow, growth plans, and of course, taxes. Staying compliant is much easier when you can see everything in one place, which is why having a reliable Maryland small business tax calendar is essential. Whether you’re a startup founder, LLC owner, freelancer, or solo entrepreneur, knowing your federal and state deadlines can help you avoid penalties, interest fees, and last-minute stress. This guide breaks down the most important Maryland and federal tax dates into a simple, one-page cheat sheet you can reference all year long.
Important Note: While we have done our best to offer an accurate and helpful year-long tax calendar, dates and regulations can change quickly. Always double-check the information for any relevant tax filings and keep an open line of communication with your business advisor, who will help you stay on top of all of your business taxes.
Why a Maryland Small Business Tax Calendar Matters
Missing a tax deadline doesn’t just mean inconvenience, it can cost real money. Filing late (or paying late) may lead to:
- Penalties and interest charges
- Delayed refunds or credits
- Increased audit risk
- Disrupted cash flow
A structured Maryland small business tax calendar keeps you organized so you can:
- Plan ahead for quarterly payments
- Track annual filings
- Stay compliant with state and federal rules
- Reduce surprise tax bills
For startups and solo owners especially, predictable scheduling = fewer headaches.
One-Page Cheat Sheet: Maryland + Federal Tax Deadlines
Use this as your quick-reference calendar for the year. Not every deadline applies to every business, but most Maryland LLCs, S-corps, partnerships, freelancers, and single-member owners will fall under at least several of these categories.
Tip: If a deadline falls on a weekend or holiday, it usually moves to the next business day.
January Deadlines
January 15: Q4 Estimated Federal Tax Payment Due
For self-employed owners, freelancers, and pass-through entities.
January 31: IRS Forms Due to Workers & Contractors
- W-2 to employees
- 1099-NEC to contractors
- Copies filed with IRS & SSA
Maryland Withholding & Employer Filings
- Annual MD withholding reconciliation (if applicable)
February Deadlines
Mid-February: 1099 & W-2 Filing with States (If Required)
Many businesses file at the same time as federal copies.
Review:
- Payroll records
- Contractor summaries
- Sales & expense documentation
March Deadlines
March 15: Business Entity Tax Returns (Federal)
Applies to:
- S-Corporations (Form 1120-S)
- Partnerships (Form 1065)
Maryland Pass-Through Entity Returns
- Maryland Form 510 (if applicable)
Extensions may be filed, but taxes must still be paid on time.
April Deadlines
April 15: Individual / Single-Member / Freelance Returns
- Federal Form 1040 + Schedule C
- Maryland Form 502
Also due:
- Q1 Estimated Federal Taxes
- Maryland Individual Estimated Taxes (if required)
This is the key date for:
- Freelancers
- Consultants
- Startup founders paying pass-through income
June Deadlines
June 15: Q2 Estimated Tax Payments
Federal + Maryland (if applicable):
- Self-employed owners
- Gig workers
- Single-member LLCs
September Deadlines
September 15: Q3 Estimated Tax Payments
Also:
- Extended partnership & S-corp returns due (if extension filed)
Great checkpoint to review:
- Profit-to-tax ratio
- Write-offs
- Year-end planning opportunities
October Deadlines
October 15: Extended Individual & Single-Member Returns
If you filed an extension in April, this is your final due date.
December Deadlines
December 31: Year-End Payroll & Recordkeeping
Before closing your books:
- Run year-end payroll adjustments
- Record asset purchases
- Finalize retirement contributions (where eligible)
Great time to meet with a tax professional or advisor.
Maryland Sales & Use Tax Filing (If Applicable)
Many Maryland small businesses must file:
- Monthly
- Quarterly
- Or annually
Deadlines depend on your assigned filing frequency.
Examples include:
- Retailers
- Service businesses charging taxable services
- Online sellers with MD nexus
Check your:
- Maryland Sales & Use Account
- Filing schedule assigned by the Comptroller
Who This Maryland Small Business Tax Calendar Helps Most
This cheat sheet is especially useful for:
- Solo entrepreneurs & consultants
- Freelancers & creatives
- Startup founders & tech professionals
- Single-member and multi-member LLCs
- S-corp owners
- Independent contractors
If you receive pass-through income or pay quarterly taxes, bookmarking this calendar is a must.
Quick Reminders for Startups & Solo Owners
Here are a few smart habits to stay ahead of deadlines:
- Set calendar reminders 2–3 weeks before each due date
- Keep separate business banking accounts
- Track expenses monthly (not at year-end)
- Save receipts & digital statements
- Talk to a CPA before switching entity types
- Review quarterly profit to adjust estimated payments
A consistent workflow today prevents tax panic later.
Final Note (Not Legal or Tax Advice)
This Maryland small business tax calendar is meant as a helpful planning guide. Specific requirements may vary based on:
- Business structure
- Revenue level
- Industry
- Filing frequency
- Local regulations
Always confirm deadlines with a licensed tax professional or the Maryland Comptroller.
Trust the Professionals at the Harding Group
Unlike other accounting firms, The Harding Group, located in Annapolis, MD, will never charge you for consultations and strive for open communication with our clients.
Are you interested in business advising, tax preparation, bookkeeping and accounting, payroll services, training + support for QuickBooks, or retirement planning? We have the necessary expertise and years of proven results to help.
We gladly serve clients in Annapolis, Anne Arundel County, Baltimore, Severna Park, and Columbia. If you are ready to take the stress out of tax time, contact us online or give us a call at (410) 573-9991 for a free consultation. Follow us on Facebook, Twitter, YouTube, and LinkedIn for more tax tips.