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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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🍀 Learn Irish Dance in Brighton! 🍀 Looking for a 🍀 Learn Irish Dance in Brighton! 🍀

Looking for a fun new activity for your child? Join the O’Shea Chaplin Irish Dancers for their Brighton Beginner Class! ☘️

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💃 Opportunities to compete & perform
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📅 Wednesdays | 4:30–5:15 PM
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@osheachaplin has been sharing the tradition of Irish dance for more than 70 years and three generations. Come learn, make friends, build confidence, and experience the joy of Irish dance!

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MoonLight Nails & Spa 💅 NEW LOOK. NEW MANAGEMENT. MoonLight Nails & Spa
💅 NEW LOOK. NEW MANAGEMENT. SAME GREAT CARE! 💅

We are excited to welcome you to our renovated salon and new beginning! Come relax, refresh, and enjoy a beautiful nail experience in our newly updated space. 💕✨

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🥐 Taste Brighton’s history as we celebrate Boston 🥐 Taste Brighton’s history as we celebrate Boston 250! 🇺🇸

Brighton Main Streets is excited to partner with Allston-Brighton Food Tours to present “Menu of the Day: Revolutionary Brighton — Discovering 250 Years of Community, Courage, and Change.”

Brighton has a fascinating place in the story of the American Revolution—and what better way to discover that history than by walking our neighborhood, visiting local businesses, sharing a meal, and learning the stories of the people and places that helped shape our community?

Join us for a FREE walking and food tour exploring Brighton’s past, present, and future:

🥞 Thursday Breakfast Tours
August 13 & 20 | 8–9 AM

🍽️ Saturday Dinner Tours
August 15 & 22 | 7–9 PM

🥐 Sunday Brunch Tours
August 16 & 23 | 11 AM–1 PM

Food is included, tours are free and open to the public, and space is limited—registration is required.

A huge thank you to Boston 250 and the partners whose support helped make this programming possible. Boston 250 is a public-private partnership between the City of Boston and private-sector partners including Meet Boston, State Street, The Boston Foundation, John Hancock, Eastern Bank, Liberty Mutual, Blue Cross Blue Shield of Massachusetts, Vertex Pharmaceuticals, and PNC Bank.

We are grateful for their investment in neighborhood programming that gives us the opportunity to celebrate Boston’s 250th anniversary right here in Brighton—and to support the local businesses and community organizations that make Brighton special.

And a special thank you to Allston-Brighton Food Tours for helping us bring Brighton’s history to life through something that has always brought communities together: food.

Come hungry. Leave knowing a little more about Brighton. ❤️

📍 FREE & OPEN TO THE PUBLIC
🍴 Food included
🎟️ Limited space — registration required
🔗 ABFoodToursBoston.com/250

#Boston250 #BrightonMA #BrightonMainStreets #AllstonBrighton #BostonHistory #RevolutionaryBoston #SupportLocal #BostonEvents
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