Join us for a night of live music at Havisham Bourbon, Brew & Spirits! We will be showcasing the talented students of the SIU School of Music in an intimate speakeasy setting. Enjoy a unique blend of jazz, blues, and more while sipping on your favorite drink. Don't miss out Read more
Whether relaxing before the rush of the holiday season or beginning your holiday shopping early, Blue Sky Vineyard is the place to be. During your visit enjoy: Wine Club Perks: Be a Wine Club Member for a day and enjoy SOME of the benefits of Wine Club Membership this weekend Read more
Wear your most festive Christmas running gear! The 5k will help kick off “Christmas in Downtown Anna” so PLAN TO ATTEND ALL THE OTHER “CHRISTMAS IN DOWNTOWN ANNA” EVENTS! •Registration for the 5K or 1-Mile Run/Walk is $20; on race day, Nov 25, registration is $25. Registration: 7:15 am 5K Read more
Light Up The Night Parade Union County Chamber of Commerce and the City of Anna are proud to host this festive and fun event in Downtown Anna! November 29, 2025 5:30 PM – 7:00 PM Downtown Anna Join us for Union County Light Up The Night Parade! This free event Read more
The River-to River Trail Society offers free guided hikes in and about the Shawnee National Forest. All hikes are open to the public free of charge. No reservations are required. These hikes are of at least moderate difficulty, and are intended for people in good health who have done some Read more
Meet the alpacas! The ranch will have Christmas decorations up and a few of our alpacas will be dressed for the occasion! Join Us for a Magical Christmas with the Alpacas Event! Get ready to make this holiday season unforgettable! Gather your loved ones and come to Rolling Oak Alpaca Read more
Municipal Building. Meet Santa, Cookies, and caroling.
2 Dates. November 29th at 7:30PM. This is a great way to finish the Christmas In Downtown Anna Festivities. It's at the Davie School Inn and doors will open at 6:30pm. This is our favorite show of the year so this year we have added a second date on December Read more
Join us for Christmas in the Courtyard on December 4th from 4:30pm-7:30pm! Take a picture with Santa, and enjoy free carriage rides graciously provided by Farmers State Bank and FSB Insurance. It's the perfect way to kick off the holiday season with family and friends. See you there! Mrs. Proctor's Read more
• Dec 5 at 7 pm, Dec 6 and 7 at 2 pm: Secret Garden: Spring Version Musical directed by Jaylyn Althoff. This enchanting classic of children's literature is reimagined in brilliant musical style by composer Lucy Simon and Marsha Norman. Orphaned in India, 11-year-old Mary Lennox returns to Yorkshire Read more
Krampus – long overlooked as Santa’s demon sidekick – is visited by Marley’s ghost on Christmas Eve in a twisted take of A Christmas Carol. But unlike Scrooge, Krampus enjoys being bad – and has no interest in redemption. This dark comedy flips the classic tale with humor and holiday Read more
Christmas Jubilee is a heartwarming holiday concert featuring a combined choir of singers from local churches and performance groups. Enjoy timeless carols, modern holiday favorites, and show-stopping performances. Performance Dates • Friday, Dec. 5 | 6:30 p.m. • Saturday, Dec. 6 | 2 p.m. Location Little Chapel Church Auditorium 3859 Read more