Moments on the Modern Trail: Chicago

The hidden gems of Chicago along our Modern Trail Mash Bash and Immersion with Brooklyn Brewery.

Cruising around cities is much better with good company, don’t you think? With that in mind, we partnered with our friends at Brooklyn Brewery to bring you the Brooklyn Brewery Mash Tour – a weekend-long city exploration centered on local music, delicious beer, and good eats. The traveling beer-lovers-dream is on the move – so join us for The Mash as we take over some of our favorite cities this fall including Philadelphia, DC, Boston, Austin, and New Orleans.

Want a sample of what’s to come? Here’s what was served up at the first stop in the Windy City.

Timberland Presents: Mikal Cronin at Thalia Hall

The Chicago Mash Tour kicked off Friday night with a free show from indie powerhouse Mikal Cronin and Chicago-locals Varsity. Meanwhile, Brooklyn Brewery kept the beer flowing, while we cranked out custom screen printed shirts on site for eventgoers.

Built in 1892, Pilsen’s Thalia Hall has deep roots in the neighborhood, which made it the proper introduction to our Pilsen Neighborhood Immersion. And with Dusek’s Board and Beer and the Punch House right downstairs, we thought we never had to leave. But there was a whole neighborhood left to explore, so we made our way to The Trailhead.

Pilsen Neighborhood Immersion

Chicago’s Neighborhood Immersion took us to lively Pilsen, where we kicked things off at our pop-up bar and shop, The Trailhead. At each city tour stop, the Neighborhood Immersion is a chance to grab your friends and explore the area through the eyes of those who know beer best – the folks at Brooklyn Brewery. 

At the Trailhead, you’ll have a chance to check out both sides of the Brooklyn Brewery x Timberland Collaboration, which includes a special bottling of Brooklyn’s experimental ghost bottles and a waxed canvas insulated beer tote. You’ll also pick up the Guide to Good Beer and a thick stack of steals to cash in on along your adventure. You can expect lunch at a local hotspot, free beer at our favorite watering holes, and a ton of other discounts in the neighborhood.

Chicago is home to 97 breweries and over 600 spots to grab a cold Brooklyn Beer. And Pilsen is no stranger to beer – the neighborhood was named by early Czech immigrants after the city of Plzeň, the birthplace of the pilsner beer style. If you missed us in Pilsen, here’s a breakdown of our Guide to Good Beer (and food too, because you’ll need to eat at some point).

Where to Eat:

Bang Bang Pie Shop

Grab a slice of pie – don’t miss their beguiling key lime – and post up in the backyard with your friends. Bang Bang Pie Shop has two locations, 2051 N California Ave. and 4947 N Damen Ave. 

Also check out: Longman & Eagle, The Publican, and Dante’s Pizza.

Where to Drink:

Lost Lake

Journey back into the glory days of tiki bars with this brightly colored cocktail den, featuring food from Thank You Chinese next door. Located at 3154 W Diversey Ave.

Also check out: Three Dots and a Dash, Thalia Hall, The Empty Bottle, Hopleaf, Sportsman’s Club, Twisted Spoke, Emporium, and Beat Kitchen


Solemn Oath Brewery

Belgian, West Coast, hip-hop, punk, and barrel-aged beers make each beer from Solemn Oath a force to be reckoned with. Located at 1661 Quincy Ave #179. 

Also check out: Half Acre Beer Company, Moody Tongue Brewing Company, Burnt City Brewing, Hopewell Brewing Company, and Marz Community Brewing Company.

Chicago, it’s been real. But we have more cities to explore – the tour has just begun. 

Want to meet us at The Trailhead? Check out what city we’re headed to next and snag your tickets.