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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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🎨🍂 @sparkalifewithart Spark a Life with ART! retur 🎨🍂 @sparkalifewithart Spark a Life with ART! returns to the Brighton Farmers’ Market TODAY!

Join us today, October 7, from 3:30–5:30 PM for the third installment of our free fall art series with Spark a Life with Art and artist Lauren McGrath, proudly sponsored by Brighton Main Streets!

👻🎃 Today’s theme: “Whimsical Halloween: Friendly Ghosts & Autumn Magic”

A playful, creative and non-scary Halloween art activity for all ages! Come get into the fall spirit and create something magical.

📍 Brighton Farmers’ Market – Brighton Common
📅 Today – Wednesday, October 7
⏰ 3:30–5:30 PM
🎨 FREE & open to all ages

Stop by, make some art, visit our local farmers and vendors, and enjoy an afternoon of community and creativity in Brighton! 🍁

A big thank you to Spark a Life with Art for continuing to bring creativity, imagination and fun to our community!

#BrightonMainStreets #BrightonFarmersMarket #SparkALifeWithArt #BrightonMA #AllstonBrighton 02135 CommunityArt HalloweenFun SupportLocal
📣 SAVE THE ALLSTON POST OFFICE! 📬 Join neighbors, 📣 SAVE THE ALLSTON POST OFFICE! 📬

Join neighbors, local businesses, and community leaders TODAY for a Rally & Press Conference with Mayor Michelle Wu and City Council President Liz Breadon in support of keeping the Allston Post Office in our community.

The Allston Post Office is more than a place to pick up the mail. It is an important neighborhood resource that residents, seniors, families, small businesses, and community organizations rely on every day. Allston deserves accessible, reliable postal service right here in the neighborhood.

📅 TODAY — Monday, October 5
⏰ 4:00 PM
📍 19 Harvard Ave., Allston
Parking lot next to O’Brien’s Pub

Come out, stand with the Allston community, and help send a strong message:

📬 SAVE THE ALLSTON POST OFFICE!

Please share and help spread the word!

#SaveTheAllstonPostOffice #Allston #AllstonBrighton #BrightonMA #CommunityMatters SupportAllston Boston USPS
We hope to see everyone tomorrow at swissbäkers fo We hope to see everyone tomorrow at swissbäkers for Coffee with a Cop! Come meet our officers from Boston Police Department District 14!
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