New Buffalo and Three Oaks, MichiganThe drive: 1.5 hours

I could tell you that my lifelong besties and I make an annual pilgrimage to southwest Michigan’s Harbor Country for the sunsets, which turn the sky and lake into a painter’s palette of lavender and saffron and indigo and invite us to contemplate the fleeting nature of beauty and time and life itself. And that would mostly be true. But even truer is that we like to drink beer in a church. And whiskey in a former buggy whip factory. And margaritas at the Stray Dog Bar & Grill. And Cabernet along the Lake Michigan Shore Wine Trail. 

If a pub crawl grew up, settled down, and invested in a nice little lake retreat, it would look a lot like southwest Michigan. Name the spirit, it’s got it. Name the vibe, it’s there. All nestled among quiet, walkable streets and charming boutiques and vintage lakeside cabins that make you feel a million miles (though actually only about 70) from Chicago’s hustle. 

Journeyman Distillery’s distilling system Photograph: Journeyman Distillery

My besties and I started consolidating our birthday celebrations into one fall getaway five years ago. It’s something of a holy miracle when we can all clear our schedules the same weekend, so it’s only fitting that we kick things off in a church. Specifically, Beer Church Brewing Co., housed inside a former Methodist church built in the 1860s. John Lustina and Jane Simon bought the structure eight years ago and converted it into a delightful brewery and pizza joint, saving it from destruction and adding just a hint of subversion to New Buffalo’s town square, which is otherwise populated by family-friendly spots like Oink’s Dutch Treat (ice cream) and Uncle Jib’s Outpost (paddleboard and kayak rentals). 

For the past two years, we’ve ventured east for an afternoon to Three Oaks, where a refurbished factory building from the 1800s houses Journeyman Distillery. A stroll up and down Elm Street looking for antiques and housewares is the perfect way to walk off the whiskey … just in time to belly up to yet another bar. Froehlich’s Kitchen & Pantry has a great selection of craft beers and, at least the late-October weekend we visited last year, a host dressed like Mike Ditka, right down to the sweater vest. How could you not love this place?

Journeyman Distillery Photograph: Journeyman Distillery

Local KnowledgeFrom John Lustina, cofounder of Beer Church

“Froehlich’s has a Trifecta Pepper Burger that has a three-pepper relish and breaded jalapeño poppers on top. It’s a blend of brisket, short rib, and sirloin. And they know the difference between rare and medium-rare. It’s such a delicious and huge burger. I’m a man that’s way too large and I still have to take half of it home.”