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Best events in
Anna

For events and things to do in Anna, IL, the local scene is rooted in small-town community and the natural beauty of the Shawnee Hills. Activity often centers on downtown's historic Main Street, while the surrounding Shawnee Hills Wine Trail provides a scenic backdrop for weekend outings. Large annual festivals at Anna City Park punctuate the calendar, bringing the whole community together for long-standing traditions.

The energy in downtown Anna is focused around its historic Main Street, where venues like Kiki's Coffeehouse host intimate performances and the Shawnee Hills Arts Council holds monthly socials.
Major community celebrations, including the long-running Union County Fair and the annual Annabelle Festival, take place at the sprawling Anna City Park.
A short drive out of town leads to the Shawnee Hills Wine Trail, where wineries like StarView Vineyards and Alto Vineyards offer regular live music and tasting events.

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Moonlight Over the Mississippi - A Witches and Warlocks Night Out 2026

Today • 3:00 PM

Old Town Cape, Inc.

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MAF Teeski & Friends

Sat, Oct 17 • 6:00 PM

Varsity Center

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SIU Alumni 2026 Homecoming Tailgate

Saluki Stadium

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Mosaic pumpkins Craft & Sip at Blue Sky Vineyard

Sun, Oct 18 • 2:00 PM

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Pilgrimage: The Holy Boulders Competition 2026

Sat, Oct 31 • 8:00 AM

Competition Site

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Vampire Murder Mystery Dinner

Sat, Oct 31 • 5:00 PM

Havisham Bourbon, Brew & Spirits

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Fri, Nov 6 • 7:00 PM

Shawnee Community College

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The Next Level: Presented by Safe House of Southeast Missouri primary image

The Next Level: Presented by Safe House of Southeast Missouri

Sat, Nov 14 • 7:00 PM

Buckner-Ragsdale Event Center

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Moonlight Over the Mississippi - A Witches and Warlocks Night Out 2026 primary image

Moonlight Over the Mississippi - A Witches and Warlocks Night Out 2026

Today • 3:00 PM

Old Town Cape, Inc.

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MAF Teeski & Friends primary image

MAF Teeski & Friends

Sat, Oct 17 • 6:00 PM

Varsity Center

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SIU Alumni 2026 Homecoming Tailgate primary image

SIU Alumni 2026 Homecoming Tailgate

Saluki Stadium

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Mosaic pumpkins Craft & Sip at Blue Sky Vineyard primary image

Mosaic pumpkins Craft & Sip at Blue Sky Vineyard

Sun, Oct 18 • 2:00 PM

3150 S Rocky Comfort Rd

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Pilgrimage: The Holy Boulders Competition 2026 primary image

Pilgrimage: The Holy Boulders Competition 2026

Sat, Oct 31 • 8:00 AM

Competition Site

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Vampire Murder Mystery Dinner primary image

Vampire Murder Mystery Dinner

Sat, Oct 31 • 5:00 PM

Havisham Bourbon, Brew & Spirits

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Frozen: The Broadway Musical primary image

Frozen: The Broadway Musical

Fri, Nov 6 • 7:00 PM

Shawnee Community College

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The Next Level: Presented by Safe House of Southeast Missouri primary image

The Next Level: Presented by Safe House of Southeast Missouri

Sat, Nov 14 • 7:00 PM

Buckner-Ragsdale Event Center

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Sat, Oct 24 • 11:30 AM GMT+4

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Tue, Oct 27 • 11:30 AM EDT

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Fri, Oct 30 • 2:00 PM GMT

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Thu, Nov 5 • 1:00 PM GMT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Perfectionnement en programmation Python [en ligne, PYT102]

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HBR Book Webinar: Resilient Optimism

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Sat, Oct 24 • 11:30 AM GMT+4

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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Fri, Oct 30 • 2:00 PM GMT

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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Washington Crossing the Delaware / The Crossing - Film History Livestream

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Frequently asked questions about Anna

Where are the best spots for live music events in Anna, IL?

The Shawnee Hills Wine Trail offers frequent live music in a scenic setting. Wineries like Alto Vineyards and StarView Vineyards regularly host performers, especially on weekends. For a more intimate experience, Kiki's Coffeehouse in downtown Anna also features local and regional acts in a cozy atmosphere.

What are some family-friendly things to do in the Anna area?

Anna City Park is a great destination for family outings. The park hosts large annual events like the Union County Fair and the Annabelle Festival, which feature activities for all ages. Downtown Anna's seasonal street fairs, like Colorfest, also provide a fun, family-friendly atmosphere.

How can I find art events and connect with the local creative scene?

The Shawnee Hills Arts Council is the hub for local arts. The council hosts gallery exhibits and holds a monthly Monthly Art Social for artists and art lovers to connect. These events are a great way to experience the region's creative community and see local work.

What kind of food and drink events happen around Anna?

The Shawnee Hills Wine Trail is central to the area's food and drink scene. Its eleven wineries host tastings and special food pairing weekends throughout the year. For fresh local goods, the Union County Farmer's Market operates weekly in downtown Anna from spring through fall.

Are there free events to attend in Anna, IL?

Many of Anna's community festivals are free to attend. Annual street fairs in downtown Anna, like Colorfest and the Annabelle Festival, offer free entry to enjoy the atmosphere, browse vendors, and see live entertainment. Exploring the Union County Farmer's Market is another free activity.

Is there much of a nightlife scene in Anna?

Anna's nightlife is relaxed and centered on community gatherings. Instead of clubs, evenings feature events like live music at wineries on the Shawnee Hills Wine Trail or karaoke nights at local spots like The VFW Post 3455. The vibe is more social and casual than a typical city scene.

What's a good date night idea in the Anna area?

A visit to a winery on the Shawnee Hills Wine Trail makes for a scenic date. Many wineries, including StarView Vineyards, offer live music and food in a relaxed setting perfect for an evening out. Alternatively, catching a performer at Kiki's Coffeehouse downtown offers a cozier experience.

Which neighborhood is best for finding community events in Anna?

Downtown Anna is the heart of the community's event calendar. The historic Main Street district hosts annual celebrations like Christmas in Downtown Anna and Colorfest. It's a walkable area where you can also find the Shawnee Hills Arts Council and Kiki's Coffeehouse for smaller gatherings.