’Twas the day post Thanksgiving and all through the town, Needham businesses hoped shoppers soon would abound.
And they’ve incentivized them to do so by bringing back the small business shopping passport. With 41 stores and restaurants participating — 14 more than last year — there will be even more chances to win a prize from one of these local spots.
Proud Mary owner Eileen Baker and TiN RABBiT owner Hilary Chandler, who organized the holiday raffle again this year, said each business will contribute a prize valued at $100. Unlike last year, however, that amount can be broken up to increase the number of winners. Most places contributed gift cards, which Baker and Chandler will assemble into prize packages.
The raffle is not just a way to boost sales, said Baker, it’s an opportunity for the owners to build camaraderie and cross promote and ideally bring in new customers.

“Gift cards are good because it could bring a new shopper. It could be someone who filled out their passport not at Proud Mary, but wins the Proud Mary gift card, and then we have a new customer,” she said. “It brings after-the-fact business in.”
Shoppers are already abuzz about the passport returning this year. “I had one customer call me twice leading up to it because she was so excited for it,” said Baker “She and her daughter finished it on Small Business Saturday and were the first to turn a passport in. They have come to make it an annual tradition. I saw her yesterday and she said she had so much fun frequenting and supporting the small businesses.”
Baker said the feedback on the increased variety of participating business has been great, and Proud Mary alone has already handed out more than 100 passports less than a week in.
This year, Needham Bank and Copley Motorcars have sponsored the holiday raffle. Chandler said their contribution will cover all printing costs, taking that burden off the business owners. “Anything extra will go to the Needham Community Council. Last year we supported the police department.”
The raffle began Nov. 28 and will run through Dec. 31. Participants must spend a minimum of $35 at participating businesses, and can only receive one stamp per store. Each individual can enter twice for the raffle. Once completed, the passports must be dropped off by Dec. 31 at Proud Mary, TiN RABBiT, or Michelson’s Shoes, and winners will be notified Jan. 10, 2026.

