Sip, Stroll & Grow: Toast of Uptown Returns April 26 — Plus a Free Business Expo Is Coming to Truman College

By Socialhood News · Il/Chicago/Uptown · April 15, 2026

Spring is in full swing in Uptown, and the neighborhood has not one but two can't-miss community events on the horizon. First, mark your calendars: the beloved Toast of Uptown returns on Saturday, April 26, for an afternoon of strolling and sipping through the beautiful Buena and Sheridan Park historic districts. The annual wine walk — organized by Uptown United and the Uptown Chamber of Commerce — takes guests on a tour of the neighborhood's charming businesses, with wine tastes and small bites at every stop along the route. It's one of Uptown's most popular springtime traditions, and tickets are on sale now at exploreuptown.org.

And if you're an entrepreneur with an eye on Uptown's booming economy, save the date for May 16: the Chicago Business Resource Expo is coming to Truman College, right in the heart of the neighborhood. Announced by the City of Chicago's Department of Business Affairs and Consumer Protection on April 9, the free expo runs from 8:30 a.m. to 1:30 p.m. and is designed to connect local small business owners and aspiring entrepreneurs with the resources they need to launch and grow. With Uptown welcoming new restaurants, retailers, and developments at a rapid clip, there's never been a better moment to plug into the city's business support network.

From wine walks to business workshops, Uptown is buzzing with opportunity this spring. Stay in the loop on all neighborhood happenings at exploreuptown.org and right here on Socialhood!

Sources:
1. https://exploreuptown.org/our-events/
2. https://www.chicago.gov/city/en/depts/bacp/provdrs/business_support_tools/news/2026/april/chicagobusinessresourceexpotoempowercurrentandaspiringbusinessowners.html