The holiday season is a magical time around Belleville, with fun traditions, outstanding local shopping, and a great selection of holiday events for the whole family. Take a free horse-drawn carriage ride for a historic holiday tour, visit the best open-air Christmas market near Belleville homes for sale, or bring the kids to see Santa on the Square. Our real estate agents have the details on fun holiday events and traditions that you can look forward to around Belleville this year.

Holiday Events and Traditions in Belleville: What to Do This Season

Belleville Christkindlmarkt – Belleville, IL

Address: IL-159 & Main St., Belleville, IL 62220

Always one of the highlights of the holiday season, the Belleville Christkindlmarkt returns once again for its 12th year of local shopping and family fun. Kick off the holiday season on Thanksgiving Weekend, with the Belleville Christkindlmarkt open every Thursday-Sunday from November 28 – December 23, 2025. The market features unique European and hand-crafted items perfect for holiday gifting, along with delicious seasonal treats and drinks to enjoy while you shop. Additionally, many of the popular holiday activities we'll cover later in the list are held in conjunction with the Belleville Christkindlmarkt, and are conveniently located nearby.

Horse-Drawn Trolley Rides – Belleville, IL

Address: First Block of E. Main St., Belleville, IL 62220

Turn back the clock to another era and explore the beauty of Belleville during the holidays with free Horse-Drawn Trolley Rides, available on weekends from November 28 – December 21, 2025. Each ride travels through historic downtown Belleville and around the decorated Public Square, starting and stopping at the first block of East Main Street. No reservations are required, with tours available on Fridays from 5:00 – 8:00 PM, as well as Saturdays and Sundays from 12:00 – 6:00 PM.

Santa on the Square – Belleville, IL

Address: Public Square, Belleville, IL 62220

Of course, the holiday season wouldn't be complete for kids without a visit with Santa, and the Santa on the Square event makes it easy to create those wonderful holiday memories with the whole family. Kids love meeting with Santa, and parents love capturing holiday photos that can be cherished for years to come. Santa on the Square is open every Wednesday-Sunday for the holiday season, from the Santa Parade on November 28, 2025 through Christmas Eve on December 24, 2025.

Gingerbread 5K Run/Walk & Kids' Dash – Belleville, IL

Address: 510 W. Main St., Belleville, IL 62220

Healthy fun is also on the calendar in Belleville for the holidays, thanks to fun events like the Gingerbread 5K Run/Walk & Kids' Dash hosted by Belleville Parks and Recreation. The fun starts at 8:00 AM on December 6, 2025, with courses that start and end at the Belleville Parks and Recreation office. The 5K Run/Walk is very family-friendly, with both strollers and kids welcome. There will also be a special race just for kids, with the annual Kids' Dash typically taking place just before the 5K Run/Walk.

36th Annual Gingerbread Contest – Belleville, IL

Address: Downtown Belleville, IL 62220

The 36th Annual Gingerbread Contest will be hosted at stores and public places around downtown Belleville from November 26, 2025 – January 2, 2026, showcasing the talents of local bakers and artisans. View amazing gingerbread creations all around town, often displayed in the front windows of shops and restaurants, while you travel from one holiday event to the next.

Searching for your next Belleville home this fall? Our local team is here to help with all of your real estate needs. Contact us to buy and sell homes throughout the Belleville, IL area.