National Small Business Month

Cambridge Celebrates Small Businesses in May!

The city of Cambridge celebrates National Small Business Week this May! All month long, there will be workshops, networking, and other fun things to do. National Small Business Month brings our community together to celebrate, uplift, and highlight local businesses in Cambridge. This May, join us for inspiring opportunities to connect and support small businesses!

• Free workshops: Learn new skills for your business. 
• Networking: Meet other business owners and make connections. 
• Community events: Join fun gatherings for everyone. 

Everyone is welcome to these events, but some events need you to sign up ahead of time. People who own businesses in Cambridge and Cambridge residents will get first spots if an event fills up. Some event details might change.

Want to help small businesses right now? 

Start the month by visiting the different shopping areas in Cambridge and buying from small businesses! Here are some ways to find them:  

• Cambridge Business Diversity Directory (online dashboard) 
• Shopping and dining recommendations in Inman Square and East Cambridge 
• Shopping and dining recommendations in Harvard Square 
• Shopping and dining recommendations in Central Square 
• Shopping and dining recommendations in Kendall Square 
• Cambridge Local First's Member Directories and Guides
• Cambridge-Somerville Black Business Network Events  

Use the #ShopCambMA on social media all month long as we celebrate Cambridge's small businesses. Use the logo available here: Cambridge National Small Business Month logo.

Thank you to partners Cambridge Chamber of Commerce, Cambridge Local First, Central Square Business Improvement District, East Cambridge Business Association, Harvard Square Business Association, Kendall Square Business Association, and Cambridge-Somerville Black Business Network. 

To learn more about all the events happening during National Small Business Month, visit cambridgema.gov/smallbusinessmonth. 

Schedule of Events 

Please check back as events may be added throughout the month. Most events are free and open to all. 

Friday, May 1, 2026 

Succession Stories: Local Lessons on Selling a Business, 9:00 – 11:00 a.m. 

Location: Cambridge City Hall, Sullivan Chamber, 795 Massachusetts Ave., Cambridge

Join us for a coffee talk about small business succession planning. Hear from local businesses about their experience selling or buying their business. This event is best for small business owners and organizations that support small businesses.

Registration required. Register here 

Friday, May 1, 2026 – Sunday, May 3, 2026 

2026 Black Business Spring Marketplace, 12:00 – 7:00 p.m.  

Location: One Brattle Square, Harvard Square, Cambridge

Shop, connect, and support amazing local Black-owned businesses in the heart of Harvard Square. Free and open to all. Sponsored by the Cambridge-Somerville Black Business Network

RSVP is encouraged, but not required. RSVP here

Wednesday, May 6, 2026  

Legacy Business Luncheon, 12:00 – 1:30 p.m.  

This event celebrates some of the oldest small businesses in Cambridge. Click here for more information on Legacy Businesses. 

This event is closed to the public. 

Wednesday, May 6, 2026

Business Networking to Celebrate National Small Business Month and Asian American / Pacific Islander Heritage Month, 4:00 – 6:00 p.m.

Location: Sumiao Hunan Kitchen, 270 Third St., Cambridge   

The Cambridge Community Development Department and the Boston Foundation’s Asian Business Empowerment Council host a networking event to celebrate our Asian-American / Pacific Islander (AAPI) entrepreneurs and business owners. Free and open to all. 

Registration is required. Register here

Selling Online with Squarespace Workshop Series, 6:00 – 8:00 p.m.  

Location: Online with Zoom  

Ready to take your retail business online? Let’s turn visitors into customers! Small business owners should leave feeling prepared to securely sell online. Business owners may need to purchase a business web domain or subscription to Squarespace. Presented by CCTV (Vinny Prezioso). Free and open to all.  

Registration Required: Register here.

Thursday, May 14, 2026

Are You Bankable? Prepare Your Business for a Loan, 6:00 - 8:00 p.m.

Location: Cambridge Public Library - Central Square Branch, 45 Pearl St., Cambridge

Need a business loan but don’t know where to start? Learn from financial experts at Zenagos and Eastern Bank. This workshop introduces key lending terms and explains what makes a business “bankable.” We will help you tell a story with your business numbers to attract lending support. After the workshop, you will leave prepared to work with a traditional bank. Cambridge businesses who attend this workshop may be eligible for free one-on-one financial coaching.

Registration encouraged. Register here. 

Sunday, May 17, 2026 

Inman Eats & Crafts, 12:00  – 4:00 p.m. 

Location: Inman Square, Cambridge 

Experience the best of Inman Square at Inman Eats & Crafts! This street fair showcases our unique shops, talented makers, and delicious food. Explore and enjoy all that Inman has to offer! Click here for more information. Free and open to all.

Thursday, May 21

Small Business Administration’s Financial Matchmaker, 9:30 a.m. – 12:00 p.m.

Location: Cambridge Foundry, 101 Rogers St., Cambridge

Are you looking for funding or assistance to start, grow, or expand your business? Network with local SBA-approved lenders and small business resource providers. Learn about the variety of resources available to help your business thrive. Discover funding opportunities to fuel your growth! 

Registration is encouraged. Register here

Sunday, May 31, 2026 

41st Annual Harvard Square May Fair, 11:00 a.m.  – 6:00 p.m. 

Location: Harvard Square, Cambridge

 The 41st Annual MayFair is back on the streets of Harvard Square on Sunday, May 31 . Experience food inspired by cultures from all over the world, unique gifts and crafts, al fresco beer gardens, music, entertainment and dance! Click here for more information. Free and open to all.

For More Information

If you have questions about Cambridge’s National Small Business Month activities, please contact Allyson J. Allen at aallen@cambridgema.gov or 617/349-9122.