Deadline calendar

Built from the listings, as of Oct 17, 2026. Dates come from the provider pages linked on each listing. Times matter: for example, the mikeroweWORKS deadline is 11:59 p.m. Pacific Time. Confirm every date on the provider's site.

Fixed dates still ahead

Rolling or ongoing

• Free community college (MassReconnect + MassEducate) (MA): No single state deadline: Mass.gov says awards are made by each college at enrollment through the year. Each college sets its own admission deadlines (for example, MassBay's page lists Aug 28, 2026 for Fall 2026 and says it is accepting Spring, Summer and Fall 2027 applications).
• Maine Free College Scholarship (community colleges) (ME): Enroll no later than Summer 2027 (2024 graduates), Summer 2028 (2025 graduates), Summer 2029 (2026 graduates), per MCCS.
• Mary Ann Handley Award (formerly PACT): debt-free tuition at CT State Community College (CT): CT's student aid page says apply by July 15 for priority; later applicants can still apply, especially for spring, while funds last.
• Rhode Island Promise (free CCRI right after high school) (RI): Tied to the term right after graduation.
• CCRI Momentum Scholarship (two free classes for returning adults) (RI): The page says the scholarship is currently offered for the Fall 2026 semester; check CCRI for later terms.
• Vermont Advancement Grant (short-term, non-degree career training) (VT): For classes starting Jul 1, 2026 to Jun 30, 2027, while funding lasts (first-come, first-served per VSAC). VSAC's FAQ says you can still apply for a course you already finished if it began in the funded year.
• WorkReadyNH (free professional-skills course) (NH): Ongoing; class schedules are posted by the colleges.
• WIOA and WorkNowNH tuition help at NH community colleges (NH): Ongoing; talk to a Career Navigator before enrolling. Some funding requires enrollment in the state program before classes start (a Reddit commenter in r/skilledtrades said the same; confirm with the program).
• Become an apprentice in Massachusetts (state Division of Apprentice Standards) (MA): Each recruitment sets its own dates; see the state's list.
• Massachusetts Building Trades union apprenticeship directory (MA): Varies by trade and local; see each program.
• Building Pathways pre-apprenticeship (free, construction trades) (MA): Information sessions held regularly through the year; sign up on the program page.
• Emerge Career free HVAC, diesel and CDL training (via MassHire Central) (MA): See each program page for dates.
• MassHire Central free training catalog (Worcester area) (MA): Each listing links to its own deadlines.
• ApprenticeshipNH (Registered Apprenticeship openings in New Hampshire) (NH): Each opening sets its own dates.
• Maine Apprenticeship Program (find an apprenticeship) (ME): Each employer sets its own dates.
• Vermont Registered Apprenticeship (how to become an apprentice) (VT): Each sponsor sets its own dates.
• Connecticut Office of Apprenticeship Training (CT): Each sponsor sets its own dates.
• CareerConneCT (free or low-cost job training) (CT): Ongoing registration.
• Become an apprentice (Rhode Island DLT) (RI): Each sponsor sets its own dates.
• Rhode Island free or reduced-cost training (including Real Jobs RI) (RI): Each program recruits on its own schedule.
• Vermont WIOA-funded training (through Vermont Job Centers) (VT): Ongoing; contact a Job Center before enrolling.
• Apprenticeship.gov Apprenticeship Finder (National): Varies by listing.
• American Job Center finder (CareerOneStop) (National): Ongoing.
• Workforce Pell Grants (short-term training, starting July 1, 2026) (National): Ongoing; file the FAFSA and ask the school which programs qualify.

Windows that already closed (watch for next cycle)

Many scholarships reopen on a similar calendar each year. These are not guaranteed to repeat.

• DEWALT Trades Scholarship (via SkillPointe) (National): 2026 cycle closed February 28, 2026. Last cycle's window opened in early November; watch for the next one.
• The River Fund Maine Trade Scholarships (western Maine) (ME): 2026 application closed Monday, May 11 (10 PM). Watch for the 2027 window, which opened in April this year.
• ABC Massachusetts Building Our Future Scholarship (MA): 2026 deadline was May 29, 2026 (apprenticeship version for the Gould Construction Institute, and the collegiate version). Check for the 2027 cycle.
• IBEW Local 300 electrical apprenticeship (Vermont) (VT): Annual application window: June 15 to August 1 (2026 window has passed; next expected from June 15, 2027 as stated each year).