Discover Berwyn Holiday Events & Fun | Festivals, Gatherings & More

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Discover Berwyn
Restaurants • Events • Hidden Gems • Local Guides

Vintage Pink Cadillac

Berwyn's Biggest Annual Events

From classic car shows and food festivals to craft beer, live music, holiday celebrations, and community traditions, Berwyn hosts incredible events all year long. Whether you're planning a visit or you're a longtime resident, here's your guide to the city's signature annual events.

Mini Golf Pub Crawl

April 18, 2026 12-6 PM

Grab your putter and 3 friends to tour the Depot District's repertoire of taverns and restaurants at the 22nd Annual Depot District Mini-Golf Pub Crawl. Each venue will display a handmade mini-golf green to challenge the event's spirited crowd!

Cruise Nites

1st & 3rd Monday's Jun-Aug 2026

Berwyn Cruise Nites are free, community car shows that take place on the first and third Monday evenings from June through August in the Historic Depot District. Held from 6–9 p.m. along Windsor Avenue, the events feature classic cars, local food and drinks, and live music. Car enthusiasts can show off their vehicles, and families are welcome to attend to enjoy the atmosphere and community spirit.

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Berwyn's Annual Community Wide Garage Sale

June 6 & 7th 2026

Community wide garage sale even all across Berwyn. Dozens of homes participating throughout the city.

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Berwyn's Pride Parade

June 27th, 2026 11-2PM

Celebrate Pride Month at the Berwyn Pride Walk, a display of community support and recognition for the LGBTQ+ community in Berwyn. Join us as we walk together to honor diversity, promote inclusion, and celebrate every identity.

Taste of Cermak

Postponed New Date Aug 13

An annual event in Berwyn where you can sample small plates and treats from various restaurants along Cermak Road. For a single ticket, attendees can enjoy a variety of food, sweets, and drink specials, with a trolley service available to travel between participating locations.

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Corrida del Mariachi 5K

August 15th, 2026

The Corrida del Mariachi 5k returns on August 15, 2026, for our 7th year Anniversary. The Corrida begins promptly at 8:00 am at 16th St. & Wesley Ave. and ends right where it started to enthusiastic cheers, music, & congratulations.
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Rt 66 Car Show

August 29th 2026

This is a yearly event every August/September on Ogden Ave which is also Route 66. Participants show off a wide variety of cars from rusty old pick-ups to original 57 Chevy’s to low riders. If you like cars, it’s definitely worth the trip at least once. There were some awesome rides!

Berwyn Brewfest Remixed

October 3, 2026

Berwyn Brewfest is getting remixed! In addition to dozens of unique craft brews, hard ciders, and seltzers, this year’s event will feature an expanded lineup of distilleries and handcrafted cocktails to explore.

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Depot District
Oktoberfest

September 18 & 19, 2026

Berwyn's annual Oktoberfest takes place in September in the city's Depot District. The family-friendly festival featured live music, food vendors, beer gardens, and a carnival.

Elfin Around
The Depot

Held Every December

Put on your best elf costume, reindeer antlers, or any festive holiday attire and join Berwyn's merriest event of the season! This holiday-themed pub crawl will have you “elfing around” the Depot District, completing a fun scavenger hunt while enjoying festive drinks or specials.

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