West Town’s Best: Dancing in the Streets & More


West Town is buzzing with excitement as the annual Dancing in the Streets (DITS) event, presented by On Tour Brewing Company, draws near. From August 4th to 6th, this unique craft beer and live music festival will celebrate art, culture, and camaraderie! Mark Legenza, the innovative founder of On Tour Brewing and a devoted jam band fan, spearheads this event. In his typical style, he ensures that it will pay honest homage to the Grateful Dead song of the same name.

In addition to DITS, West Town is teeming with an array of events and activities throughout the month of August. From Mondays in Dorothy to West Town First Fridays, there is something for everyone to enjoy. Let’s dive into the details of DITS and other exciting happenings in the neighborhood!

Dancing in the Streets

Dancing in the Streets, West Town

DITS is an annual extravaganza that brings music lovers, beer enthusiasts, and community members together for one weekend. The event showcases West Town’s burgeoning craft beer scene alongside a lineup of live music performances. From local food vendors to talented makers, DITS promises a memorable experience for all attendees.

Inspired by the memory of Jerry Garcia, the founder of the Grateful Dead, DITS aligns with the “Days Between.” The week is dedicated to celebrating Garcia’s birthday (August 1st) and commemorating the day he passed away (August 9th). Mark Legenza’s passion for both music and craft beer has made Dancing in the Streets a must-attend event for music enthusiasts and beer connoisseurs alike.

Other West Town Events

Monday, 7/31

Mondays in Dorothy: This unique musical experience invites visitors to step away from the ordinary and embrace new themes and genres of music. In July, the theme is “BETTER THAN THE ORIGINAL,” featuring covers and remixes across different genres and decades. The DJ duo, Do not Disturb, will be rocking the house with their LGBTQ+ community representation and passion for music.

Pro/Am Open Mic Night: On Tour Brewing hosts this event every Monday, showcasing Chicago’s finest musicians, both known and undiscovered. Musicians of all levels get a chance to perform their tunes in the tasting room, making it a vibrant and dynamic night of music.

Wednesdays On Tour Brewing in West Town

Wednesday, 8/2

Wednesday Celebrations at On Tour: On Wednesdays, On Tour Brewing offers a midweek celebration with live music and great beer. Visitors can enjoy a rotating cast of Chicago’s finest musicians or a stream of a full Grateful Dead concert. It’s the perfect way to break up the week and enjoy some excellent tunes.

Thursday, 8/3

“Magical Girls” Fundraising Event: On August 3rd, Dorothy hosts a fundraising event for the queer coming-of-age short film “Magical Girls.” Attendees can enjoy magic shows, tarot readings, visual art, merchandise, and more, all supporting the creation of this beautiful film.

Friday, 8/4 – Sunday, 8/6

Jake Paul vs Nate Diaz Preview Image

West Town First Fridays: This program fosters connections among West Town’s galleries, artists, collectors, and patrons. Participating locations vary each month, so check out the Instagram Guide and walking route map to plan your art-filled evening.

National Oyster Day at Frontier: On August 5th, Frontier celebrates National Oyster Day with a special “Shuck, Sip, & Savor” happy hour. Guests can enjoy oyster and drink specials, making it a delightful way to indulge in this delectable treat. For more ideas on where to celebrate National Oyster Day, click here.

Jake Paul vs. Nate Diaz Viewing Party: Sports fans can witness an explosive showdown between questionable superstar Jake Paul and former MMA icon Nate Diaz on August 5th. Mac’s Wood Grilled offers a great viewing experience with drink deals and a lively atmosphere.

West Town

West Town is truly a vibrant and happening neighborhood, and the upcoming events in August are a testament to its rich culture and sense of community. Whether you’re a music lover, an art enthusiast, or simply seeking a good time, Dancing in the Streets and the plethora of other activities in West Town offer something for everyone to enjoy! 

For more information about West Town events and updates, visit the West Town Chamber of Commerce’s website.

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