Christmas Markets Near Windsor 2026

35 christmas markets near Windsor.

Springfield's Festival of Trees presents a grand holiday celebration. For families seeking a charming afternoon, consider the free Shop, Sip & Stroll in Branford.

Explore diverse holiday shopping experiences across Windsor and surrounding towns, from large-scale tree showcases to intimate craft fairs.

All Christmas Markets Around Windsor

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Frequently Asked Questions

Which Christmas markets should I visit in Windsor?

The W.E. Made It: Holiday Market at Jackson Park is Windsor’s marquee holiday market, held every Friday and Saturday during the Bright Lights Windsor festival. Smaller craft fairs and artisan markets also take place in various neighborhoods, offering a range of local goods and seasonal treats.

When and where are the major Christmas markets held in Windsor?

The W.E. Made It: Holiday Market runs every Friday and Saturday during Bright Lights Windsor at Jackson Park, typically from late November through early January. Check local listings for dates and times of other neighborhood markets and craft fairs in Windsor.

Do Windsor Christmas markets charge admission?

Most holiday markets in Windsor, including the W.E. Made It: Holiday Market, are free to attend. Some special events or vendor experiences may have a fee, but general market access is open to all.

Are there family-friendly activities at Windsor’s Christmas markets?

Yes, many markets offer activities for all ages, including visits with Santa, holiday train rides, and live entertainment. The Chalet at Jackson Park provides a cozy spot for families to relax and enjoy food and drinks together during the market season.

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