Small Business, Big Dreams Contest

At Rockland Trust, we know that behind every small business is a big dream—and we want to help bring yours to life! 


Rockland Trust Small Business Big Dreams contest.
Congratulations to the Rockland Trust 2026 Small Business, Big Dreams Contest Grand Prize Winner!
 

CRAIC SAUCE



Meet the 2026 Finalists


Craic Sauce
Dainty Scripts
Fortin Gage

 

Rockland Trust Small Business, Big Dreams Contest provides small businesses for a chance to win our $25,000 to fuel businesses the next stage of growth. Whether you’re expanding your service offerings, investing in equipment, or researching a new location, this could be the opportunity you’ve been waiting for to take that next step. Plus, two additional finalists will each receive $5,000 to support their business goals.*

 

Previous Contest Winners

Rockland Trust Small Business, Big Dreams former winners of the grand prize.
 
*No purchase necessary. An account will not increase the chances of winning. Void where prohibited. Open to legal residents of MA, RI, and NH who meet the eligibility criteria set forth in the Official Rules. Entrant must be an authorized agent of a for-profit small business that is headquartered in these areas, which has been in continuous operations selling a product or service and under the same majority ownership for at least two (2) years, with annual revenues under $3,000,000. One (1) entry per business. Entrant must be 18 or older. Sponsor reserves the right to modify dates. Additional restrictions apply; see Official Contest Rules or request a copy by calling 508.732.7078.

Come Back in 2027

Our Small Business, Big Dreams Contest will return in 2027 with another chance for entrepreneurs to shine. Keep building, keep dreaming, and check back next year for your opportunity to apply and become our next winner.

Frequently Asked Questions

Beginning March 2027, you can take our qualification survey using the 'Get Started' button!

If your business was disqualified during the survey, please review our Official Contest Rules. There are a number of reasons this may have happened, such as the location of the business or how long it has been in operation.

If you're applying on behalf of a non-profit (501(c)(3), you may be eligible for support through our Charitable Foundation HERE.

If you have questions regarding your disqualification, please email SmallBusiness@RocklandTrust.com.

After completing the qualification survey, if you quality—you will receive an email with a link to the required submission questions. 

From that same page, you will upload your final submission as a Word or PDF file. Submissions must not be over five (5) pages in length.

If you do not receive an email after completing the survey, please email SmallBusiness@RocklandTrust.com.

Rockland Trust will notify all applicants by email with an update on their submission status.