Step into the spirit of the holidays during the Small Business Saturday Holiday Stroll on November 29. This family-friendly day invites visitors to shop local, enjoy live music, glide on the ice-skating rink, and savor the festive charm that makes Holidays in Highlands shine.
The streets come alive with The City Carolers, a professional a cappella quartet whose rich harmonies and Dickens-inspired costumes bring timeless Christmas cheer to Main Street.
Don't miss the Black Friday Sale at Acorns and a stroll through The Christmas Tree. Between shopping stops, take a spin around the Ice-Skating Rink in Kelsey-Hutchinson Founders Park (open from 1-10pm) or warm up at The Bascom's Holiday Market, where local artisans showcase handcrafted treasures and festive décor. Whether you’re browsing for the perfect gift or simply soaking up the spirit of the season, Highlands offers the perfect mountain escape.
Small Business Saturday Holiday Stroll
Saturday, November 29
11:30am–4pm along Main Street
Downtown Highlands celebrates local shopping with festive fun, treats, and performances throughout the day:
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11:30am: Storytime at Hudson Library
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12–2pm: Southern Highland Band perform live bluegrass
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1:30–2:30pm: Face painting at The Bascom
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2:30pm: The City Carolers in full Victorian garb stroll Main Street with classic carols
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Enjoy candy canes from the Highlands Police Department, and holiday photo ops and special offers from local shops.
Looking for more holiday fun? Stay for our Christmas Tree Lighting in the Park from 6-8pm on the same day! Click Here to learn more about Holidays in Highlands Events.