Chicago’s Bucktown neighborhood, just north of Wicker Park, is the city’s rising star, and an afternoon dedicated to Bucktown shopping is an afternoon well spent. The affluent residential neighborhood was once an artists’ community. Record stores, resale shops, and coffee houses are a reminder of the creatives who still reside here. The Bucktown area has especially thrived with boutique shopping, gourmet dining, and a converted train-track walking trail that’s longer than New York’s High Line.
Start your day strolling west on North Damen Avenue, beginning just north of North Avenue. New-to-Chicago stores such as Shinola, which boasts gorgeous wood shelves lined with Americana and all things heritage, and TOMS, the purposeful shoe brand whose Bucktown location includes eyewear and a fair-trade coffee shop, gives you a glimpse into the thriving community. But there’s a little something for everyone if you keep walking north. High-quality men’s and women’s boutiques are mixed in with some unique finds including one of the few U.S.-based stand-alone stores of perfume retailer, Diptyque.
For unique local finds, stop by p.45 and browse their edited racks of stylish women’s clothing made by nationally known Chicago designers. Don’t miss their shoe collection in back as well as a few classic handbags and modern jewelry pieces. There’s also Goddess and the Grocer. It’s one part market and one part restaurant, which makes it the perfect place to break for a light lunch, a quick snack, or a gourmet gift to go. Debate over the hearty soups, classic sandwiches, thoughtful gift boxes, and indulgent coffee drinks downstairs before heading upstairs to enjoy their charming rooftop patio. Your legs can rest while your eyes stay busy watching the interesting crowds on Damen Avenue.
Now that you’re re-energized, continue north on your shopping excursion. Eventually, you’ll spy a pedestrian overpass up ahead. This is the Bloomingdale Trail. Walk up the tree-lined ramp and onto the paved path for an elevated view of Bucktown life. You’ll get to peek into the gorgeous condos and single-family homes that line this former train track. Walk beside moms pushing double strollers, kids on bikes, and young couples with their dogs. The path stretches 2.7 miles and has parks and benches along the way for when your feet need yet another break.
Find your way back to Damen Avenue and exit the Bloomingdale Trail, heading north. Swing into Apartment Number 9, a men’s boutique specializing in high-quality clothing with an impeccable fit. They’re known for featuring pieces with subtle detailing that’s comfortable and classic. There is also a wall of hipster-worthy Warby Parker frames for you to peruse. Keep heading a few blocks north to Stitch, which has been a Bucktown shopping destination for almost 20 years. You won’t know which way to look first when you step inside. The unique store is stocked with modern accessories for men, women, and homes, including furniture, jewelry, and handbags all made by emerging designers.
By now, you’ve likely worked up an appetite again. You’ll never regret stopping for appetizers or dinner just one block further north at Le Bouchon, at the corner of Armitage and Damen. It’s a charming French bistro that operates as if it were truly located in Paris. The fact that it’s always packed is part of the charm, so revel in the cramped bar area with a glass of wine as you wait for a table to open. Order the moules à la Provençale to start. They’re steamed with vermouth, tomato, basil, and fennel, which you can soak up with crisp bread. Finish the late afternoon with one more glass of wine. You didn’t eat dinner as late as the French do, but you ate just as well.