Special Events in Wicker Park & Bucktown

Concerts, Festivals & More!

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Renegade Craft Fair is one of our favorite neighborhood festivals for stocking up on gifts! We are always excited to host vendors who know that we are a short walk to the fair when thinking about transporting their goods back and forth. We encourage you to book in advance (this festival is held the first weekend after Labor Day in September every year.) 

This is a family-friendly festival that takes up most of Division St. between Damen & Paulina. Local restaurants provide snacks and drinks. This festival also comes back in December for last-minute gifts! 

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Bucktown Apple Pie Contest is held every fall in the Holstein Park Fieldhouse at Palmer and Oakley. Our innkeeper Robin even entered one year! After the judging pie slices are sold to benefit the Friends of Holstein Park. It's a really fun event and who doesn't like apple pie? 

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Bucktown Arts Fest is an annual street fair adjacent to Holstein Park. Great crafts, food and beers to go around. Another great opportunity to support local artists in Chicago! This is a family-friendly event. 

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Wicker Park Fest is held every summer on Milwaukee Ave. between Damen & Paulina. This festival is usually a small $5 donation and always boasts a great lineup of live music! In addition to live music, a lot of local stores and restaurants set up to sell goods and offer promotions. This is one we look forward to every year!