Small Business Month 2026: Nine Events Owners Can Register for Now

Small Business Expo, America's largest small business event series, connects more than 100,000 business owners annually — and its New York and Boston stops in May anchor a month of programming for entrepreneurs during National Small Business Month.

The Small Business Administration (SBA) opens the observance with National Small Business Week 2026, running Sunday, May 3, through Saturday, May 9. The SBA hosts the week to support and show appreciation for entrepreneurs across the country. Organizations including the U.S. Chamber of Commerce extend the celebration through the entire month with in-person events and online sessions for seasoned owners and aspiring founders alike.

Here are nine events open for registration.

CO— Small Business Day 2026 — Thursday, May 7

CO— by the U.S. Chamber of Commerce kicks off Small Business Month with a day of learning and networking for small business owners. Attendees will learn how to strengthen their business with insights from leading executives on policy, cybersecurity, retail, and more. This year's event is hybrid: main stage programming runs both virtually and in person at the U.S. Chamber of Commerce headquarters in Washington, D.C. In-person attendees can also join a hands-on AI training session and an exclusive wine-tasting reception after the main stage programming. Registration is open on the CO— Small Business Day homepage.

NSBW Virtual Summit — Tuesday, May 5, and Wednesday, May 6

The SBA's free two-day virtual summit features educational presentations from industry leaders, exhibit booths, free resources, and expert advice from Small Business Development Centers (SBDCs). Entrepreneurs can register online to reserve a spot.

U.S. Chamber of Commerce Foundation Virtual Broadcast — Tuesday, May 5

As part of the Foundation's 2026 Building Resilience Conference, this virtual broadcast highlights the Small Business Readiness for Resiliency Program (R4R), a multi-year initiative supporting preparedness for disaster-affected small businesses across the country. Representatives from the program's sponsors and partners will discuss R4R's impact and how small businesses can participate.

Inc. Small Business Week — Monday, May 4, through Friday, May 8

The Inc. Small Business Week Series, produced in partnership with Shark Tank, brings together business leaders to share their playbooks for scaling and strategic leadership. Virtual sessions run daily from 2:00 to 3:00 p.m. ET, covering topics from AI automation to customer engagement in an algorithm-driven world. Registrants can select the sessions that fit their schedule.

Thurston Economic Development Center: Intro to Business — Wednesday, May 6

Pre-business and early-stage entrepreneurs can join a free live webinar from 9 to 10 a.m. PT (12 to 1 p.m. ET) covering the fundamentals of business planning and the steps to turn a vision into reality. Registrants receive a Zoom link 24 hours before the event.

Lieutenant Governor's Small Business Academy — Tuesday, May 5, through Friday, May 8

Wisconsin Economic Development's free annual academy supports owners in launching and scaling their operations. Programming includes practical advice from successful entrepreneurs plus workshops on financing, legal and regulatory issues, and business certifications. Virtual sessions run Tuesday, May 5, through Thursday, May 7, with in-person components across Wisconsin on Friday, May 8.

Small Business Expo — May 7 in New York, May 27 in Boston

The free-to-attend expo series runs in the Northeast this Small Business Month. The New York City spring session takes place at the Javits Convention Center on Thursday, May 7. The Boston session follows on Wednesday, May 27, at The Westin Boston Seaport District.

Freedom Makers Monthly Momentum Meeting — Thursday, May 14

Freedom Makers Virtual Services, which connects small businesses with military spouse virtual assistants, hosts a free monthly networking session on Zoom at 2:00 p.m. ET. The May meeting gives entrepreneurs, small business owners, and nonprofit leaders a forum to discuss business strategy and make connections.

NJSBDC Workshops — Throughout May

The New Jersey Small Business Development Center runs online workshops — many free — on starting, running, and growing a business. May offerings include sessions on AI tools for productivity, government contracting opportunities, and social media and content marketing strategy.

Owners outside New Jersey have options too. Several SBDCs across the country, including those in Arizona, Missouri, and Virginia, will host similar event series, and the SBA website lists the nearest center. With most of these programs free or low-cost, the barrier to entry for owners seeking expert guidance this May is essentially registration deadlines.