You can credit Greendale’s charm to its unusual history. During the Great Depression, President Franklin Roosevelt launched one of the most ambitious affordable housing projects in American history.
The idea was to buy rural land near major cities and create tiny utopias. This happened in Maryland, Ohio and, of course, Greendale, Wisconsin. The result is a quirky, walkable town with a personality worth exploring.
Tell us who you’d pick to be a Betty this year!
1. Serendipity
5602 BROAD ST.
Located downtown next to the surprisingly lifelike statue of Norman Rockwell, this boutique features vendors from all over Wisconsin. It’s like shopping at your favorite seasonal craft market, except it’s open year-round. Find décor, handmade gifts, clothing and more.
2. Día y Noche
6601 NORTHWAY
This colorful spot is a cafe by day and restaurant by night. Stop in early for Latin American-style beverages and bakery, or grab dinner – the menu changes quarterly and travels across Latin America. Served up iced or hot, the signature latte de coquito is a must, with espresso, coconut milk, cinnamon and vanilla syrups, whipped cream and nutmeg.
3. Scout Lake
5902 W. LOOMIS RD.
Head to Scout Lake to get your steps in. This lily-pad-covered fishing hole is a popular spot for anglers and speed-walkers alike. The main hike is a flat, paved half-mile loop that’s great for laps, but there’s also some fun off-roading to be done in the nearby woods. Pro tip: Check the logs along the shore for groups of sunbathing turtles.
4. Vintage 38
5690 BROAD ST.
This cozy wine bar sports a deliciously long list of options poured by the glass, bottle or flight and a lovely outdoor patio along Broad Street. Vintage 38 specializes in wine that is limited in production or from artisanal winemakers who use Old World techniques. The tap beer list is usually solid, too.
5. The Steakout
6300 INDUSTRIAL LOOP
You’ll get the quintessential supper club experience here, relish tray and all. The spot is known for its friendly owners, devoted following and quality dishes. “It’s the place to go for a drink or to have a really good steak,” Cyborowski says.
6. Field Workshop
5686 BROAD ST.
This art studio – “a great community space,” Cyborowski says – features a glow-in-the-dark splatter room, a drop-in tinker lab (offering crafting, beading, STEM activities) and more. He recommends signing up for one of their monthly paint and sip events.
7. Sugar & Flour
5721 BROAD ST.
Cyborowski is a regular at this lovely bakery and cafe. He enjoys their omelets and sandwiches – from a four-cheese avocado grilled cheese to pot roast on a baguette. Don’t walk out without a s’mores cookie, which he says is “the best cookie I’ve ever had in my life.”
