holiday shopping trail

How It Works

Shop local this holiday season and enter to win great prizes! The Holiday Shopping Trail is online this year with challenges you can complete every day. The more you click, share, and shop, the more chances you have to win!

Play to win the Grand Prize—a $500 splurge at the business of your choice!—or one of many great prizes from shops, restaurants, and venues on the Trail, including gift cards, gift baskets, gadgets, home items, and more!

Grand Prize: $500 to the business of your choice Terms apply.

Second Place: $250 worth of gift cards to participating businesses

Third Place: $100 worth of gift cards to participating businesses

Plus, you get entered to win a random prize drawings – gift cards, gift baskets, and more – just for participating!

See the participating businesses below. More prizes coming soon!


It’s never too late to sign up!

4 Ways to Shop Local

The 2020 Holiday Shopping Trail & Challenge is sponsored by

the day Comcast Business

Thank you to our partner organizations:
Old Saybrook Chamber of Commerce | Southeastern CT Cultural Coalition

Thank you for participating in our Holiday Shopping Trail!

Winners will be notified by email shortly.

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Where to Shop

Filter the table by business category or location and click the + to see if your favorite business is currently running any holiday specials!

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