As the leaves start to change and the crisp fall air settles in, September is the perfect time to explore all that Milwaukee has to offer. Whether you’re planning a second date or rekindling romance, the city’s rich blend of outdoor and cultural activities makes for a memorable experience. Here are some fun and safe date ideas to enjoy in Milwaukee this September.

1. Stroll Through the Milwaukee Public Market

Start your date with a visit to the bustling Milwaukee Public Market in the Historic Third Ward. Sample fresh seafood, handmade chocolates, or artisan cheeses as you walk hand-in-hand through the market. Grab lunch from one of the vendors and enjoy your meal on the outdoor patio, which offers a view of the surrounding neighborhood.
Pro Tip: Finish off your trip with a coffee or dessert from a local spot like Colectivo Coffee, just a short walk away.

2. Explore the Milwaukee Riverwalk

The Milwaukee Riverwalk offers the perfect mix of scenery and city vibes, with its peaceful riverside paths and stunning public art displays. Spend the afternoon walking along the three-mile trail, which winds through downtown Milwaukee, passing by shops, restaurants, and breweries. Stop at a local spot like Lakefront Brewery for a drink or take a break to watch the boats go by.
Bonus: Keep an eye out for the iconic Bronze Fonz statue along the way for a fun photo opportunity!

3. Take a Brewery Tour

Milwaukee is known as “Brew City” for a reason, and no date in the city is complete without sampling some local brews. Take a tour of one of Milwaukee’s historic breweries, such as the Pabst Brewery or Milwaukee Brewing Company, where you can learn about the city’s brewing heritage and sample fresh craft beer.
Tip: Many breweries now offer guided tours with limited group sizes, so be sure to check availability and book ahead.

4. Relax at Bradford Beach

September is the last chance to enjoy Milwaukee’s gorgeous lakeside beaches before fall truly sets in. Head to Bradford Beach for a relaxing day by Lake Michigan, where you can take a walk along the sandy shore or dip your toes in the water. Pack a picnic and enjoy the peaceful lake views, or stop by the beachside tiki bar for a refreshing drink.
Pro Tip: Arrive in the evening for a romantic sunset date with the stunning Milwaukee skyline as your backdrop.

5. Take a Cruise on the Milwaukee Boat Line

Get a unique view of the city by taking a boat tour on the Milwaukee Boat Line. Cruise along the Milwaukee River and out onto Lake Michigan while learning about the city’s history and landmarks. There are themed cruises available, including happy hour or sunset cruises, perfect for a relaxed and scenic date on the water.
Tip: Book tickets in advance, and choose an open-air deck for the best experience!

6. Attend Milwaukee’s Oktoberfest

Milwaukee’s German heritage shines during Oktoberfest, with celebrations happening throughout the city in September. Head to the Bavarian Bierhaus for traditional German food, music, and, of course, plenty of beer. Dance the night away to live polka music, try a stein-holding competition, and enjoy the lively atmosphere with your date.
Tip: Opt for an outdoor beer garden setting, where you can enjoy the festivities with fresh autumn air.

7. Catch a Movie at the Avalon Theater

For a cozy date night, head to the historic Avalon Theater in Bay View. The theater offers a vintage movie experience with plush seating and a charming, old-school vibe. Choose from the latest releases or classic films, and enjoy dinner and drinks served directly to your seat. September evenings are perfect for a low-key date at one of Milwaukee’s best independent cinemas.
Pro Tip: Reserve seats in advance to ensure you get the best spot, as the theater is popular for its cozy atmosphere.

8. Bike Along the Oak Leaf Trail

If you’re feeling active, rent bikes and take a ride along Milwaukee’s Oak Leaf Trail. This scenic path winds through parks, neighborhoods, and along the Lake Michigan shoreline, offering beautiful views of the city. Stop for a break at a local café or enjoy a lakeside picnic together.

9. Visit the Milwaukee Art Museum

For a more cultured and artistic date, spend an afternoon exploring the Milwaukee Art Museum. Its stunning architecture and diverse collection of exhibits provide plenty of conversation starters. Wander through the galleries, admire the famous Quadracci Pavilion, and take in the breathtaking views of Lake Michigan from the museum’s grounds.
Pro Tip: Visit on the weekend to catch the iconic “wings” of the museum’s Burke Brise Soleil as they open and close at noon.

10. Take a Day Trip to Cedarburg

If you’re looking for a picturesque fall day trip, head to Cedarburg, just a 30-minute drive from Milwaukee. This charming town is known for its quaint shops, historic buildings, and beautiful fall foliage. Stroll hand-in-hand through Cedar Creek Park, visit the local wineries for a tasting, and stop by a café for coffee or hot cider.
Bonus Tip: Cedarburg’s Wine & Harvest Festival in late September is a great chance to enjoy local food, drinks, and live music in a cozy small-town setting.

Milwaukee is filled with fun and unique date options that are perfect for enjoying September’s crisp air and autumnal beauty. From lakeside strolls to cozy brewery tours, these ideas will help you create a memorable, safe, and romantic experience for you and your date.