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Small Business, Big Dreams! $25,000 Grand Prize Contest

By: Julie Gosselin
Published: March 2, 2026
Categories:
Small Businesses

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!

Official Contest Rules

Beginning March 2, you can enter the Rockland Trust Small Business, Big Dreams Contest for a chance to win our $25,000 Grand Prize to fuel your 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.*

There are two steps to the Small Business, Big Dreams Contest application process:

Step 1: You must qualify! Once you’ve reviewed the Official Contest Rules, beginning March 2nd, you can take the qualification survey by clicking the ‘Get Started’ button.

Get Started!

 Step 2: If your business qualifies, you will complete a written business overview with detailed responses to the questions requested by Rockland Trust. We ask that submission be no longer than five (5) pages to be considered.

You’ve submitted your entry. Now what?

Rockland Trust will select and interview eight (8) semifinalists. Based on these interviews, three (3) finalists will be selected and partnered with a Rockland Trust business banker to develop a business plan for review by our panel of judges. The panel will deliberate and select one lucky business owner to be the winner of the $25,000 grand prize! Both runners-up will each receive $5,000.

Follow along with us!

(Note that all dates are subject to change)

March 2 at 9:00 a.m. ET Contest Submission

Period Opens

  • One you have reviewed the official Official Contest Rules, select the ‘Get Started’ button to take our qualification survey!
  • If your business qualifies, you will receive an email with details for completing the final submission.
March 31 at 5:00 p.m. ET Contest Submission

Period Closes

  • Submission window will close at 5:00 p.m. ET.
  • No late submissions will be accepted.
April 13 Semifinalists Selections
  • Eight (8) semifinalists are virtually interviewed by Rockland Trust and Boston 25 News.
April 24 Finalist Selections
  • Finalists are paired with a Rockland Trust business banker to create a business plan presentation for a panel of judges.
  • Finalists shoot a promotional video with Boston 25 News, highlighting their business – this video will air on TV for everyone to see!
(On or About) June 2 Final Contest Judging
  • Shot in-person at Boston 25 News in Dedham, MA.
  • All finalists must be able to attend the final judging in-person on June 2.

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Finishing out the week and ready to celebrate summ Finishing out the week and ready to celebrate summer with our neighbors at Faneuil Gardens for their Annual Unity Day Celebration! We also got to celebrate with the kids of Brighton Future Forward. This program is run through our partners from @allstonbrightoncdc. The afterschool program provides academic support, youth development and enrichment opportunities for the kids at Faneuil and we had a great year participating with the program! We hope everyone has a happy summer! #brightonma #brightonmainstreets #unityday #community
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We were so excited to be able to attend the @bosto We were so excited to be able to attend the @bostonoeoi @cityofboston Legacy Business Awards and celebrate our two amazing Brighton businesses chosen for the honor! @amandasflowers6560 and @devlins02135 collectively have over 60 years in business in our community and we are so grateful and proud! Their longevity in our neighborhood represents a legacy of dedication, trust, and commitment, providing generations of residents with reliable service while helping to strengthen the character and vitality of our community. We want to thank @bostonoeoi @bostonmainstreetsfoundation and everyone who nominated and voted for our winners! We want to congratulate all of the legacy businesses winners across the city for their contributions. Special shout out to Ben Tocchi from @staterepmike for attending the event in support of our small businesses. We were happy to be in solidarity with our fellow main streets directors @hydeparkmainstreets and @missionhillmainstreets! The Bruce Bolling building in @nubiansquaremainstreets district of Roxbury provided a perfect backdrop for such a beautiful evening! #brightonmainstreets #brightonma #legacybusiness #eatandshoplocal
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