Worcester, MA Networking Events You Don't Want to Miss - May 2025 Edition
- Makin' It Marketing
- Apr 30
- 3 min read
Looking for the best business networking events in Worcester, MA this May? This curated list of events in Worcester, MA is made for you if you're a small business owner, seasoned entrepreneur, freelancer, or growth-minded professional. This month is packed with opportunities to make new connections, build your referral network, and expand your visibility across Central Massachusetts.
From casual meetups and virtual panels to conferences and cause-driven community events, this list features Worcester’s top May 2025 networking events — all organized in chronological order with links to register. If you’ve been searching for “Worcester, MA networking events,” “entrepreneur meetups near me,” or “business events in Central MA,” you’re in the right place.
May 2025 Worcester, MA Networking Calendar - At a Glance
Date | Event Name | More Info | Location |
Thursday, May 8th | Celebrate & Connect Virtual Networking | Zoom | |
Friday, May 9th | Woostapreneurs Forum | Worcester, MA | |
Saturday, May 10th | 2nd Annual Cornhole Tournament – Team Ava | Nichols College, Dudley, MA | |
Wednesday, May 14th | Women in Business Sturbridge Networking Event | Sturbridge, MA | |
Wednesday, May 21st | Fun at 5 at Rapscallion | Spencer, MA | |
Wednesday, May 28th | Central Mass Women’s Group Mix & Mingle | Worcester, MA | |
Thursday, May 29th | Mastermind Conference | Worcester, MA |
Networking Events in Worcester, MA This May
Celebrate & Connect: National Small Business Week Virtual Event
Thursday, May 8th, 2025
Hosted on Zoom, this Massachusetts statewide virtual networking session invites small business owners to build connections and have meaningful conversations in rotating breakout rooms. A great fit for those looking to expand their network without leaving the office.
Woostapreneurs Forum
Friday, May 9th, 2025
The Worcester Chamber’s Woostapreneurs Forum is a free event that brings together entrepreneurs and small business leaders from across the city. Attendees can expect educational sessions, networking opportunities, and insight from business support organizations.
2nd Annual Cornhole Tournament – Team Ava
Saturday, May 10th, 2025
Taking place at Nichols College Football Field from 12:00 to 3:00 PM, this community fundraiser supports pediatric Fanconi cancer research. The event includes food trucks, a live auction, raffles, and games. Registration is $100 per team, and teams who sign up by May 1st receive a tournament T-shirt.
Women in Business Sturbridge Networking Event
Wednesday, May 14th, 2025
Women in Business Sturbridge hosts monthly events that foster collaboration and support among local women professionals. This May gathering will offer attendees a chance to build new connections and grow their network in a welcoming space.
Fun at 5 at Rapscallion
Wednesday, May 21st, 2025
This after-hours Chamber mixer will be held at Rapscallion in Spencer and offers a relaxed setting for professionals to enjoy food, drinks, and casual conversation with other members of the business community.
Central Mass Women’s Group Mix & Mingle
Wednesday, May 28th, 2025
Led by Meagan Matthy (That Dental Office Manager) and Tara Ostromecky (Makin' It Marketing), this free, informal ladies' night event invites local women to come together over light appetizers for connection and conversation. No sales pitch — just community.
Mastermind Conference
Thursday, May 29th, 2025
This day-long event hosted by Ryan Richards and Ben Carbone at Off The Rails in Worcester brings together real estate professionals, business owners, investors, and entrepreneurs. Attendees will hear from speakers, connect with like-minded individuals, and leave with tangible takeaways.
So, Will We See You There?
No matter your industry or experience level, showing up to the right networking events can open doors to new opportunities, partnerships, and support for your business. With options ranging from virtual chats to in-person mixers and full-day conferences, Worcester’s May 2025 networking events offer something for everyone.
Be sure to bookmark this post, share it with a colleague, and subscribe on our homepage to stay updated on the latest business events in Worcester, MA and beyond. Reach out — we’re here to help Worcester businesses keep connecting and keep growing.
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