SPEND LOCAL. WIN LOCAL.

Choose Highwood as your top shopping and dining destination on
Small Business Saturday. Then turn your receipts from Highwood
stores, businesses, bars, and restaurants into Holiday Raffle tickets for a
chance to win a $50.00 gift card from any Highwood Chamber business.
The winning ticket will be drawn December 5 on Facebook Live.

PRESENTED BY :                               SPONSORED BY

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NOV. 28

SMALL BUSINESS
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SATURDAY

Spend Local. Win Local.
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AND Santa Parade

The biggest Highwood for the Holidays activity takes place on Small Business Saturday, November 28. Highwood is using the occasion to celebrate its distinction as a top shopping and dining destination. Visitors who spend the day spending money in Highwood stores, businesses, and restaurants can turn their receipts into Holiday Raffle tickets for a chance to win a $50.00 gift card for any Highwood Chamber business. Receipts should be emailed to info@highwoodchamber.com by Monday, November 30. One raffle ticket will be issued for every $100 spent in Highwood on November 28, with a maximum of five tickets issued for receipts totaling $400.00 or more. The winning ticket will be drawn December 5 at noon on Facebook Live. To delight the youngest members of the family visiting Highwood on Small Business Saturday, Santa will parade through downtown at 4 p.m. escorted by the Highwood Fire Department and the Chamber will set up a COVID-friendly candy cane booth in front of City Hall where the kids can write letters to Santa. 

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NOV. 25

Thru
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DEC. 24

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vote here

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Business Window Wonderland
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Competition

A unique holiday window decorating contest that directly benefits local shops, bars, restaurants, and businesses will light up Highwood for the Holidays starting November 25. Participating locations will compete with each other to put up glittering, wonder-filled window displays and seasonal décor that everyone can enjoy while strolling along the sidewalk or from the comfort of their cars. Residents and visitors can vote as many times as they like for their favorites at www.highwoodchamber.com. Each vote will cost $1.00, with all the vote proceeds gifted to the business selected. In addition, anyone posting a photo of their favorite window to social media with the hashtag #HighwoodHolidays and tagging the Chamber will be entered in a weekly drawing for a $5.00 gift card for a Highwood Chamber business. 

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NOV. 10

Thru
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NOV. 30

Festive Family Photo
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Contest

​This year, it’s also possible to snap the winning shot for the annual holiday card and win this year’s Festive Family Photo Contest at the same time. Sponsored by The Smilelist and Loft 329, the contest is all about great local poses that showcase Highwood’s holiday spirit. Contestants should post their photos on the Highwood Chamber Facebook page or other social media platform with the hashtag #HWDHOLPIC and tag the Highwood Chamber. Winners will be selected in four categories: Best Location in Highwood, Most Festive, Best Family and Pet Shot, and Most Unique.