Milwaukee Through the Lens of an Urban Planner 

What better way to experience Milwaukee than through the lens of an urban planner? Brittany Simmons, a city planner by day and content creator by night from Detroit, Michigan, set out to explore Milwaukee on foot, by boat, bike and bus, discovering just how much of the city you can experience without spending your weekend behind the wheel. 

Her getaway paired Bublr Bikes and The Hop with neighborhood gems, Black-owned businesses, lakefront stops, local food and plenty of Milwaukee flavor along the way. 

Follow Brittany’s itinerary for inspiration and discover just how easy it is to experience Milwaukee one neighborhood at a time. 

Day 1: Meet Milwaukee’s Neighborhoods 

Stay: The Plaza Hotel Milwaukee

Check into The Plaza Hotel, a historic Art Deco-inspired hotel just blocks from the lakefront. Head downstairs to Café at the Plaza for a late lunch, where you can grab a table in the ivy-covered courtyard before heading out to explore.

Spend the Afternoon in Bronzeville 

Make your way to Bronzeville, a neighborhood deeply rooted in Milwaukee’s Black history, culture and entrepreneurship. 

Start at Niche Book Bar, a Black-owned bookstore dedicated to celebrating Black literature across genres. Then stop by 414loral, a Black woman-owned floral shop along Historic King Drive.
 

Sip Something Different 

Continue exploring with a stop at HoneyBee Sage & Wellness Apothecary Cafe, a local spot offering herbal teas and handcrafted nonalcoholic drinks. 
 

Find a New Urban Oasis 

Head west to Davidson Park, a 4.8-acre public park on Harley-Davidson’s corporate campus. Opened in 2024, the park transformed part of the Near West Side into a community gathering space filled with greenery and thoughtful design. 
 

Dinner in Bay View 

End your first full afternoon of exploring with dinner at Room Service in Bay View. If you still have room afterward, make time for one of Milwaukee’s essential desserts: frozen custard. Try a scoop at Kopp’s or Leon’s. 

Day 2: Explore Milwaukee on Two Wheels 

Coffee With a View 

Start the morning at Colectivo Coffee - Lakefront, housed inside a restored 1888 Milwaukee River Flushing Station. As the sun rises along the water of Lake Michigan, you’ll be itching to get out there. 
 

Explore Lake Park 

From there, spend some time in Lake Park, designed by renowned landscape architect Frederick Law Olmsted. Wander its wooded paths, find the North Point Lighthouse and take in views overlooking Lake Michigan. 
 

Grab a Bublr Bike 

Now it’s time to see Milwaukee on two wheels. Hop on a Bublr Bike and make your way toward Bradford Beach, one of the city’s most popular stretches of Lake Michigan shoreline. 

Milwaukee’s lakefront trail makes the journey part of the experience, giving you plenty of fresh-air views along the way. 
 

Bike to a Beer Garden 

Keep pedaling south toward Roundhouse Beer Garden at McKinley Marina. Grab a brat or pretzel and a drink, then find a spot overlooking the marina for a quintessential Milwaukee lunch break. 
 

Trade Two Wheels for The Hop 

Continue toward downtown before swapping your bike for The Hop, Milwaukee’s streetcar. Catch it near The Couture and ride into the Historic Third Ward. 
 

Shop and Stroll the Third Ward 

Spend the afternoon exploring one of Milwaukee’s most walkable neighborhoods. Browse local shops, wander along the Milwaukee RiverWalk and take in the mix of historic warehouses and modern restaurants, galleries and boutiques. 
 

Taste Your Way Through the Milwaukee Public Market 

When hunger hits, head to the Milwaukee Public Market. With independently owned merchants under one roof, everyone can build their own dinner, from Wisconsin favorites to seafood and international flavors. 

If you’re looking for a sit-down alternative, head to Amilinda for Chef Gregory León’s Spanish and Portuguese-inspired cooking. 
 

Keep the Night Going 

Grab a drink at the Third Ward Beer Garden or catch skyline views of Milwaukee at The Outsider. Or venture into another neighborhood for a nightcap like At Random, which has been serving cocktails in Bay View since 1964. It’ll have you stepping back into time with their mid-century ice cream drinks and cocktails; be sure to order the Pink Squirrel, or else it’s not a successful Milwaukee trip. 

Day 3: Markets, Makers & More Milwaukee Flavor 

Start Downtown 

Begin the morning at 3rd Street Market Hall with coffee and breakfast from Café Bebe, then take a look around The Avenue, a former downtown mall transformed into a mix of offices, apartments, dining and gathering spaces. 
 

Shop Like a Local 

On a summer Sunday, head to Shorewood Farmers Market at Estabrook Park. Browse local produce, food and goods while experiencing another piece of the Milwaukee area’s neighborhood culture. 
 

Finish at Zócalo 

Close out the weekend at Zócalo Food Park in Walker’s Point. Milwaukee’s first food truck park brings together a rotating mix of cuisines, local makers and a full-service tavern in a communal indoor-outdoor space. 
 

Brittany’s weekend proves you don’t need a car to pack plenty of Milwaukee into a getaway. So, grab a Bublr, catch The Hop and build your own Milwaukee adventure.

Find Your Milwaukee