Small Business Calendar 2026: Key Dates for Business Owners in Canada

Here we are at the outset of a brand new year. You’ve likely planned well in advance to tackle and achieve your small business’s sales and project goals in 2026, but it can be easy for important upcoming dates throughout the year to slip your mind as you make the shift into high gear.

Starting a new year on the right track is essential. But there are some dates and deadlines that no small business owner or independent professional should overlook.

From tax return deadlines to business insurance renewals to administrative tasks, our small business calendar serves as a reminder of key dates so nothing is accidentally missed.

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January 2026

• Determining your business’s budget: If you haven’t already, map out your business’s 2026 financial position and sales forecasts.

• Business insurance renewals: Although due dates vary, many small businesses’ and self-employed professionals’ insurance policies are up for renewal at the start of the year. It may be time to get a free insurance quote to see if you can secure better coverage at a lower cost, or for new businesses, it’s definitely the time to do so.
  
  Business owners should review their existing policies and consider what has changed in their operations in 2025 to ensure their renewed policies adequately address their liability risks going forward. 

• January 31: GST/HST payments are due if your business files sales taxes each quarter for taxes collected from October to December. Most GST/HST registrants can use NETFILE, the Canada Revenue Agency’s (CRA) online tax-filing portal.

February 2026

• February 16: Family Day (as it’s called in Ontario) is a national holiday that occurs on the third Monday in February. Its name varies by province.

• February 24: The CRA is expected to open NETFILE for employees, self-employed individuals, and sole proprietors to file their tax returns on this date.

• February 28: Employers must issue T4 slips (employment income) to their employees by this date.

March 2026

• March 1: The start of Fraud Prevention Month, which runs through to the 31st. This annual awareness campaign educates consumers and business owners on how to spot and prevent fraud.

• March 2: The deadline to contribute to a Registered Retirement Savings Plan (RRSP), Pooled Registered Pension Plan (PRPP), or Specified Pension Plan (SPP). 

• March 8: International Women’s Day. This global campaign celebrates the achievements of women and aims to drive gender parity. Celebrate the women on your team and in your life, and consider offering limited-time discounts on goods or services your business provides to female customers.

• March 31: Ontario-based businesses with Workers’ Safety and Insurance Board (WSIB) coverage must submit their 2025 payroll reconciliation if they report monthly.

April 2026

• April 3: Good Friday is a federal statutory holiday observed in all provinces and by employees covered by Canada’s labour laws.

• April 6: Easter Monday is an optional holiday in most provinces.

• April 30: If a sole proprietor or self-employed professional owes the Canada Revenue Agency (CRA)  money, settle up on this date or the CRA will begin charging you daily compound interest as of May 1.

May 2026

• May 4: It’s the start of Emergency Preparedness Week, which runs until May 10. This annual campaign aims to raise awareness to tackle emergencies by identifying local hazards and taking action to minimize those risks.

• May 11: May is an ideal time to get your business summer-ready. For example, for professional services organizations and consultants, it’s a good time to extend audit offers to customers and prospects, whether your focus is on finances, technology services, or marketing.
  
  For landscapers and lawn care professionals, gym owners and fitness instructors, health and wellness professionals, and life and career coaches, May is an excellent time to promote summer packages to your target customer base.

• May 18: Victoria Day is a statutory holiday in most provinces. It’s often called the “May Long Weekend” and marks the unofficial start of summer.
  
  It’s when peak season typically begins for campgrounds and RV parks. If you own and operate a campground or RV park, be sure to get the comprehensive business insurance policy you need before the season starts.
  
  It’s also around this time that many seasonal farmers’ markets and street festivals kick off in communities large and small across Canada. 

June 2026

• June 1: Many business owners and independent professionals wisely do a midyear business insurance review in June. A Zensurance broker can help review your existing policy and recommend changes if necessary to close any gaps in your coverage.
  
  For example, consider adding business interruption insurance to a commercial property insurance policy to cover your operational expenses if you’re forced to close for repairs following an insurable loss, such as a fire.
  
  Additionally, it’s a good idea to get a free quote to see if you can get better coverage or the same coverage you need at a lower premium. You can switch insurance providers at any time, but if you cancel an existing policy early, you might not be entitled to a pro rata refund of the premium paid. 

• June 15: Most sole proprietors and self-employed professionals must file a tax return by or before this date.

• June 30: For corporations with a December 31, 2025, fiscal year-end, T2 corporate tax returns are due on this date.

July 2026

• July 1: Canada Day is a national holiday celebrating the anniversary of Canadian confederation. Wave the flag and celebrate our beautiful country!
  
  However, as it’s a national statutory holiday, for most employers that means you must either give employees a paid day off or pay them additional statutory holiday pay on this date.
  
  Also, if your business is closed on July 1, don’t forget to update your Google My Business profile and website to state that, and communicate it on your social media networks in advance.

• July 31: GST/HST payments are due if your business files sales taxes each quarter for taxes collected from April to June.

August 2026

• August 3: Civic Holiday is a public holiday observed in most Canadian provinces.

• August 10: Back-to-school season is next month! Many private tutors, teachers, and academic professionals need to get or renew their liability insurance before Labour Day.

• August 17: Treat August as the launch ramp ahead for September and for the busiest quarter of the year – October to December. For example, if you need to hire seasonal or temporary help for September or the holiday season, start recruiting in August. Or, if it’s necessary to make tweaks or changes to your systems – point-of-sale, CRM, online reservation bookings – do it before the busy season hits.

August is also a good month to review your revenue, profit margins, and mission-critical projects initiated in the first seven months of the year, to help set clear, achievable sales targets and goals for the balance of the year.

September 2026

• September 1: For snow removal contractors and landscapers offering snow removal services who haven’t yet obtained snow removal insurance, this is the time to get covered before winter’s arrival.

• September 7: Labour Day is a Canada-wide statutory holiday. Just as you would for Canada Day, remember to update your Google My Business profile and website to reflect any closure. Be sure to communicate this in advance on your social media channels.
  
  For retailers, Labour Day sales can boost their bottom lines and clear out summer inventory, while for restaurant owners, it’s a good time to transition to autumn-themed menus.
  
  Meanwhile, for business consultants, your customers are likely starting to plan their budgets and projects for next year. Reach out to them and pitch pilots and retainers, or host webinars, lunch-and-learns, and in-person events.

October 2026

• October 1: Cybersecurity Awareness Month begins and runs to the end of the month. Its goal is to educate businesses and consumers on how to stay safe online and practice smart cyber hygiene habits.
  
  This date also marks the start of Small Business Month in Canada – when small businesses are recognized and celebrated nationwide for their entrepreneurship, resilience, and collective contribution to our country’s success. 

• October 4: Fire Prevention Week runs from October 4 to 10 in Canada. The annual campaign focuses on fire and burn prevention education for households and business owners alike. For Canadian businesses, it’s an ideal time to review workplace fire safety protocols and ensure your insurance coverage includes business fire protection. 

• October 12: Thanksgiving Monday is a national statutory holiday. The Thanksgiving long weekend is also an excellent time to offer your customers exclusive, limited-time discounts and set the stage for Black Friday and the holiday shopping season by providing discounts on future purchases in November and December to woo them back.

• October 31: GST/HST payments due if your business files sales taxes each quarter for taxes collected from July to September (and it’s Halloween!).

November 2026

• November 1: If you have a business vehicle or manage a fleet of commercial vehicles, it’s time to winterize your ride, and especially, get winter tires installed. Many insurers may provide a small discount on your commercial auto insurance premium if you have winter tires on your commercial vehicles from November 1 to April 30.

• November 11: Remembrance Day is our annual observance that marks the end of World War I and is a holiday in many provinces.

• November 27: Black Friday – one of Canada’s biggest retail sales days of the year and a key date for retailers in-store and online.

• November 28: This day marks Small Business Saturday – an annual, national celebration to encourage Canadians to support small businesses in their communities as the holiday shopping season gets underway.
  
  Ramp up your Black Friday deals on Small Business Saturday by offering exclusive, one-day flash-sale discounts, or discounts on future purchases to entice customers who buy from you to return and buy again before the year ends.

• November 30: Cyber Monday is another critical online selling date for retailers and independent sellers. Unlike Black Friday, Cyber Monday focuses on online shopping with big discounts on primarily tech gadgets, smart devices, electronics, and software.
  
  But don’t forget to ensure your business has product liability insurance to cover third-party bodily injuries or property damage caused by any physical or digital product you manufacture, distribute, or sell.

December 2026

• December 1: Annual malpractice insurance renewals for dental hygienists in Ontario.
  
  December is either your business’s busiest and most critical month of the year, or a quiet time perfect for preparing for January.
  
  For retailers, hospitality, and personal services businesses that rely on the holidays to boost sales, early December offers a chance to enhance your sales strategy by rolling out holiday-themed bundles, seasonal discounts, and upselling gift cards to drive repeat business. These 10 holiday retail planning tips can help generate ideas that may work for your business.
  
  If December is your company’s ‘quiet time’, use it to plan for next year. For example, if costs are on the rise, finalize and pre-announce any price increases for your goods and services, set 2027 revenue and profit goals, and map out your budget and cash flow expenses so you’re ready to go in January.

• December 16: Annual malpractice insurance renewals for dental hygienists in B.C.

• December 31: Annual malpractice insurance renewals for Registered Nurses and Registered Massage Therapists in most provinces. It’s also New Year’s Eve!

Be 2026 Ready With Low-Cost Business Insurance for Your Small Business

A vital part of ensuring your business is ready for 2026 to achieve its growth goals is protecting your finances and assets with a comprehensive business insurance policy.

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Zensurance is Canada’s leading online small business insurance brokerage. With access to over 50 partner insurers, we can secure the ideal policy that matches your budget and addresses your specific risks quickly and completely online.

– Reviewed by Ryan Insalaco, Practice Leader, Digital Solutions Team, Zensurance.