May 2026’s Top Startup Events in Boston
- Stephanie Roulic
- May 1
- 5 min read
May is shaping up to be a massive month in Boston’s startup ecosystem, with a packed calendar of events bringing together founders, operators, investors, students, and ecosystem builders. From Boston Tech Week and Robotics Tech Week to climate gatherings, venture capital dinners, product showcases, and founder-focused networking, this month is all about momentum, collaboration, and building what’s next.
Startup Boston is helping anchor the month with a series of community-powered experiences. Here are four to have on your radar:
Cofounder Matching (May 4) - perfect for both folks with and without a startup idea who are excited to become a founder
From Vibe Coding to Viable Products: How AI-Native Teams Ship (May 6) - we’re teaming up with OrangeLoops to break down how AI-native startups are moving beyond “vibe-coding” and building real, scalable products
Skip the Pitch, Try the Product: Test Early-Stage Startups IRL (May 26) - be the first to experience the products being built right here in Boston
TBD Angels Happy Hour (May 28) - Startup Boston is partnering up with TBD Angels to host an epic happy hour bringing together the entire startup community during Boston Tech Week
Whether you’re actively fundraising, exploring emerging technologies like AI and robotics, looking to meet potential cofounders, or simply trying to plug deeper into the community, May offers no shortage of ways to get involved. Below is a roundup of the top startup events happening across Greater Boston this month - each one a chance to learn, connect, and build alongside the people shaping the future.
May’s Top Startup Events
Techstars Startup Weekend Boston
Date: Friday, May 1 - Sunday, May 3; Learn more and register
Discount code: 20% off with code STARTUPBOS
Organizer: Boston New Technology
a 54-hour experience where aspiring founders pitch ideas, form teams, and build real prototypes - no prior experience or team required. Attendees get the chance to meet potential cofounders, collaborate with people who know how to ship, and turn ideas into something tangible in one weekend instead of waiting months.
Boston Climate Week
Date: Sunday, May 3 - Sunday, May 10; Learn more and register
Organizer: ClimateBase
Boston’s largest climate-focused week, bringing together seven days of events, conversations, and community action dedicated to accelerating the city’s sustainable future. The week connects residents, founders, operators, policymakers, and advocates through programming designed to spark ideas, collaboration, and measurable impact.
The Legends Of Venture Capital
Date: Tuesday, May 5 from 5:00pm - 7:00pm; Learn more and register
This intimate session will bring together leading founders and operators for a candid discussion on venture capital, company building, and what it takes to scale enduring businesses in today’s market. Guests can expect an evening of insight, perspective, and meaningful connection with two of the minds helping shape the future of innovation.
She Builds Boston: Brewing Bold Ideas
Date: Wednesday, May 6 from 9:30am - 11:00am; Learn more and register
Organizer: Startup Boston
Our monthly gathering for female investors and female founders of product-driven startups (i.e. software, hardware, life science and consumer products). This event consists of both structured and open networking.
Eastward x NEVCA Rising VC Leaders Dinner
Date: Thursday, May 7 from 6:00pm - 9:30pm; Learn more and register
Organizer: New England Venture Capital Association
The gathering will bring together Principals and emerging leaders from across the New England venture ecosystem who are actively shaping investment strategy and growing into the next generation of firm leadership.
UXPA Boston 2025 Conference
Date: Friday May 9; Learn more and register
Organizer: UXPA
A leading UX conference for New England and the Greater Boston area, with the 2025 theme, Shaping Change: Design for a Dynamic World. Professionals from around the world will gather for a full day of insightful presentations, interactive workshops, and networking opportunities focused on the latest trends and techniques in user experience design.
Fireside Chat with Paul English (Cofounder & CTO, Kayak) | Presented by TNT
Date: Tuesday, May 12 from 5:00pm - 6:00pm; Learn more and register
Organizer: TNT
TNT is hosting a fireside chat with Paul English, the entrepreneur and technologist best known for co-founding Kayak, one of the most influential travel platforms on the internet. This conversation will explore his path from software engineer to serial founder, along with lessons on building product-driven companies and scaling startups through multiple stages of growth.
RESOLVE: The MassChallenge Annual Gathering
Date: Wednesday, May 13 from 5:30pm - 8:00pm; Learn more and register
Organizer: MassChallenge
MassChallenge is bringing its community together once again for RESOLVE '26, the annual night where founders, investors, partners, alumni, operators, and civic leaders come together to celebrate the people building what’s next. After 16 years of ecosystem impact, this signature gathering is designed as an evening of convergence, connection, and real conversation with food, drinks, live music, and immersive experiences.
Greentown Labs x TEDxHarvard Square Climate AI Hackathon
Date: Thursday, May 14; Learn more and register
Organizer: TEDxHarvard Square and Greentown Labs
A full-day hackathon at Greentown Labs, bringing together founders, engineers, researchers, and operators to build at the intersection of climate tech and AI.
The Blueprint Showcase
Date: Wednesday, May 20 from 2:00pm - 5:30pm; Learn more and register
Organizer: The Engine
A full-day, invitation-only gathering where teams from the 12th S2026 Blueprint cohort present their technologies, receive live feedback from expert judges, and celebrate the culmination of the program alongside The Engine community. In the afternoon, the event opens to the broader Tough Tech ecosystem for poster sessions, stage presentations, and networking with founders building first-of-a-kind technologies.
Dealflow Mixer: Meet CIC’s Social Impact Cohort
Date: Thursday, May 21 from 9:30am - 11:30am; Learn more and register
Organizer: Startup Boston & CIC
Startup Boston is thrilled to welcome investors to meet CIC’s Social Impact Cohort - a powerhouse lineup of startups led by historically underserved entrepreneurs from Massachusetts. This is a targeted networking and matching event designed to connect complementary funders and founders, fostering meaningful relationships and potential investment opportunities.
Robotics Tech Week
Date: Tuesday May 26 - Friday 29; Learn more and register
A city-wide collection of high-impact events and networking opportunities launched in Boston, one of the world’s oldest hubs for robotics innovation. Designed to bring together founders, operators, investors, researchers, and industry leaders, the week focuses on advancing robotics and AI venture building and scaling. Attendees can expect meaningful connections, fresh ideas, and a front-row seat to the future of intelligent systems.
Boston Tech Week
Date: Tuesday, May 26 - Sunday, May 31; Learn more and register
Organizer: a16z
For the first time, Andreessen Horowitz is bringing Tech Week to Boston from May 26–31, joined by more than 80 founding hosts representing the best of Boston’s tech ecosystem and beyond. The week will feature a citywide lineup of events, conversations, and networking opportunities spotlighting the founders, builders, and companies shaping the future of innovation.
Some honorable shoutouts for events you’ll want to have on your radar:
May 26: Boston Tech Week wakeup run
May 26: Skip the Pitch, Try the Product: Test Early-Stage Startups IRL
May 27: Ditch the Deck
May 27: Innovation unConference
May 28: TBD Angels Happy Hour
Boston Life Sciences Showcase: In Conversation with Mohan S. Iyer: From Genentech to IndieBio
Date: Friday, May 29 from 12:00pm - 2:00pm; Learn more and register
Organizer: The Startup Oasis Network
The bi-monthly series is designed to create high-impact connections between startup teams and aligned funders while advancing collaboration across the life sciences ecosystem. This edition features Mohan S. Iyer of SOSV, whose career spans leadership roles at Genentech, Tethys Bioscience, Second Genome, and Pendulum Therapeutics. Attendees can expect candid insights on investing in deep tech startups, what first-check investors look for, and live feedback as three selected startups pitch directly to Mohan.
Check out our full event calendar right here to stay connected with the Boston startup community. Also, remember to subscribe to our newsletter using the form below for monthly updates!
