Published On August 15th, 2018

Creative Fall Date Ideas in Milwaukee

Fall is right around the corner and it can be a busy time for people. The feeling of summer calmness has left the air, the kids are back in school, and the days are getting shorter. It can be a tough time for dating, but it’s also one of the most beautiful times of the year – so we think you should probably get out and about with your significant other. We recently read an article that featured 200 date ideas – who has time to read that?? We know you don’t, so we took the time to read all 200 and pair it down to our 20 favorites because let’s face it – making time for date night is tough enough, and taking the time to plan it is even tougher. So sit down for 5 minutes, read this article, and really “wow” your significant other on your next date night with something that neither of you has ever done before… and if you do have the time to read it, here’s the article with 200 Milwaukee date ideas.


Date Idea #1: TNT Adventure

We’ve all seen American Ninja Warrior, but what about giving it a go for yourselves? They’ll take you through a warm-up, a course demonstration, and then free time to do the workout prescribed by the trainer, or do you own! The course is 11 lanes of obstacles and about 21 obstacles. This, of course, is challenge by choice – so just show up and see what you can do!


Date Idea #2: The Rock Snowpark

Okay, so technically, this one is a Winter date, but it was too good to leave out! Show up for the evening (4 pm – 9 pm) during the week (Monday – Thursday), and get unlimited tubing for just $16! With 19 lanes of tubing open, you can spend the evening taking laps on the snow hill.


Date Idea #3: Palermo’s Pizza Tour

Who doesn’t love pizza? Take a tour of Palermo’s and see where the magic happens for this frozen pizza company. After the tour, they’ll take you to Pizzeria 3301 (located at their company headquarters) where they serve pizza (obviously), sandwiches, soups, salads, desserts, and more!


Date Idea #4: Uptown Art

Uptown Art in Sussex is a place for beginners to gather (talk about a great first date idea), and to try their hand at painting. Uptown Art provides hands-on instruction, paint supplies, canvases, and aprons – everything you need for a night of fun! Did we mention that they have a full-service bar as well? Drink your favorite beer, wine, or cocktail while you paint!

Uptown Art Date Night in Milwaukee
Take your date out for an evening of painting and drinking – talk about a great combo!


Date Idea #5: Boswell Books

Boswell Book Company is located just north of downtown Milwaukee and right on the Milwaukee Bay – how about a nice afternoon cruising around this book store, finding a new book, and catching up on some reading? Doesn’t sound like a bad date spot at all!


Date Idea #6: Pedal Tavern

Of course, we had to throw Pedal Tavern in (it was also on the list of 200), and maybe we’re a bit biased, but we really think that we have one of the best date spots in town! We run public tours so you can come by yourself and meet other fun groups on your tour. Bring some beers and enjoy an afternoon cruise around Milwaukee with your favorite person. Even if you’ve lived in Milwaukee your entire life, we’re pretty sure you’ll leave us with a new appreciation for Milwaukee.


Date Idea #7: Kettle Moraine Ranch

Kettle Moraine Ranch is self-described as, “Wisconsin’s Best Western Town for Weddings, Horseback Rides, Event Venues, Camping, and More”, but we think you should probably find out for yourself. Everyone knows that horseback rides are about as romantic as it gets so surprise your loved one with an afternoon in the saddle!


Date Idea #8: Paddle Tavern

Again, we had to throw Paddle Tavern in. Once again we might be a bit biased, but what better date than an evening on the Milwaukee River? Once again we offer public tours so don’t worry about bringing out a big group. Just bring out your significant other, some adult beverages, and catch the sunset behind the Milwaukee skyline while pedaling your way around the Milwaukee River.


Date Idea #9: MobCraft Brewing

Have you heard of MobCraft Brewing? They brew crowdsourced beers – each month you can submit an idea for a beer you would like to see, then they put the recipes up for a vote, and the one with the most pre-orders get made! The good news is – they have a taproom where they serve up their flagship beers, crowdsourced beers, and beers from their Wild & Sour Program. Not to mention they have foosball, ping pong, live music, and outdoor seating. Sounds like a pretty nice date night!


Date Idea #10: Brew City Kayaks

We love the Milwaukee River – so what better place for a night with your loved one? It’s just $40 to rent a kayak or SUP for 4 hours (they even have season passes)! You can even take a tour if you’re new to the area or are unfamiliar with kayaking and paddleboarding!


Date Idea #11: Milwaukee Art Museum

Who doesn’t love a day of art? They’re open everyday from 10 am – 5 pm and on Thursdays they stay open until 8 pm – so leave the office a little early on Thursday, and meet your wife, husband, girlfriend, or boyfriend for an evening stroll through the art museum.

Milwaukee Art Museum Date Night Downtown Milwaukee
Enjoy a day of taking in some fine art in downtown Milwaukee.

Date Idea #12: Milwaukee Food & City Tours

Take a tour of Milwaukee’s neighborhoods that were originally settled by Italian, Irish, Polish, and German immigrants. Their tours are the ideal combination of food, culture, and history. Spice up your next dinner date night with a night of more than just dinner.


Date Idea #13: Nine Below

Nine Below is miniature golf 9 feet underground and it’s definitely one of the more unique date ideas. Reserve your TeeTime for a 2-hour round of Maker’s Golf, where you’ll design and build your own mini golf hole. After you’ve designed your hole, you’ll play a 9-hole course with the holes that other teams in your round created. Did we mention also that they have a bar?


Date Idea #14: Duffy Boats

Our duffy boats are a sophisticated way to take to the Milwaukee River without the need to own a sophisticated boat. Bring out a group of 14 (maybe a large group date) for a couple hours cruising around the Milwaukee River. The Duffy Boats are fully electric and as easy to drive as a golf cart!


Date Idea #15: Milwaukee’s Comedy Cafe

Grab your date and hit Milwaukee’s Comedy Cafe for a night of laughs! Everyone loves laughing, and if your date doesn’t, well it might be time to look for another date. Reserve a table, have a couple drinks (they have a two drink minimum), and take in some comedy for the evening.


Date Idea #16: Marcus Theatres

At Marcus Theatres, you can catch a Tuesday night move for only $5. Sounds like date night should be on a Tuesday night this week!


Date Idea #17: UWM Planetarium

The University of Wisconsin Milwaukee has a planetarium and it’s worth checking out if you’ve never been! It’s worth checking out even if you have been before – there’s probably something more you could learn about space. Living in a city can make it tough to see the stars, so bring your date out for a night of stargazing.

UWM Planetarium Creative Date Night Ideas Milwaukee
Take your date to space at the UWM Planetarium.

Date Idea #18: The Dinner Detective

The Dinner Detective is America’s largest interactive comedy murder mystery dinner show. You get to solve a hilarious crime while you feast on a fantastic dinner. The culprit is hiding in plain sight somewhere in the room, and you might even be a prime suspect. Talk about a unique dinner date night!


Date Idea #19: Bel Air Cantina

Did someone say $2 tacos and beers? Tuesdays and Thursdays at Belair Cantina are two nights that you do no want to miss! They serve up $2 tacos, $2 mexican taps, $2 select canned beers, and $2 mystery tequila shots. $2 mystery tequila shots are a deal worth taking Wednesday or Friday morning off of work for!


Date Idea #20: Foundation Bar

It’s fall and winter is around the corner – get your last beach time in at Foundation Bar and sip on their famous Mai Tai and experience Polynesian culture at it’s finest. Not only is Foundation Bar Milwaukee’s favorite tiki bar, but they’ve been consistently voted as one of the top ten tiki bars in the world!


We’ve done the legwork for you to pare down the list of 200 into 20 of our favorites – so grab your favorite person and try something new this fall. Milwaukee is an amazing city with a ton to do, make sure you see as much of it as you can, and of course, make sure you get out for a Pedal Tavern or Paddle Tavern tour with us!