Annual Events in Old Town

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Annual Events in Old Town Chicago

Old Town Theater Week – Feb. 24 – March 1, 2020
The Third Annual Old Town Theater Week will happen the last week of February in 2020. This yearly celebration of the robust theater community includes week-long deals across Chicago’s historic Old Town neighborhood, allowing residents and visitors a chance to experience Old Town’s historic theater scene.

Small Business Week – May 3-9, 2020
The Old Town Merchants and Residents Association participates in the national Small Business Week by hosting different workshops and social events for small businesses in Old Town.

The 46th Annual Wells Street Art Festival – June 13-14
Art enthusiasts are guaranteed to find plenty of inspiration at the Wells Street Art Festival, which will be held for the 46th time in 2020. Held on the popular Wells Street strip between North Avenue and Division in Chicago’s historic Old Town neighborhood, it’s a treasure trove of creativity and much more.

Over 200 juried artists from across the nation will descend upon Wells Street to showcase their respective crafts. From traditional painting to sculpturing, artisan woodworking to metalsmithing, jewelry to the digital arts, and much more, there is something for everyone.

Second Annual Old Town Restaurant Walk – July
Experience the incredible food scene in the Old Town neighborhood unlike you’ve ever done before. Sample tastes from different restaurants as you traverse the neighborhood along your chosen route.

LiveWell Week – Oct. 5 – 11, 2020
In the lead up to the Chicago Marathon, which runs through Old Town on Wells Street, the Old Town Merchants and Residents Association holds LiveWell Week, an event highlighting the health and wellness businesses in Old Town. The week consists of different experiences put on by the business community including fitness classes and nutrition seminars.

Old Town Tree Lighting – November
To welcome the holiday season, the Old Town Merchants and Residents Association holds an annual Christmas Tree lighting each November.

A Night Out in Old Town
One of the Old Town Merchants and Residents Association’s most popular events are their Nights Out in Old Town. These events consist of dinner at an Old Town restaurant and a ticket to a performance at an Old Town theater.

Seasonal Socials
Throughout the year, the Old Town Merchants and Residents Association will hold seasonal socials to bring the community together for networking in a casual setting.