Memorable Date Activities In Madison Wisconsin

Women's Dating

6 Memorable Date Activities for Couples in Madison, Wisconsin

Amber Brooks

Written by: Amber Brooks

Amber Brooks

Amber Brooks is the Editor-in-Chief at When she was growing up, her family teased her for being "boy crazy," but she preferred to think of herself as a budding dating and relationship expert. As an English major at the University of Florida, Amber honed her communication skills to write clearly, knowledgeably, and passionately about a variety of subjects. Now with over 1,800 lifestyle articles to her name, Amber brings her tireless wit and relatable experiences to She has been quoted by the Washington Times, Cosmopolitan, The New York Post, and AskMen.

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Edited by: Lillian Castro

Lillian Castro

Lillian Guevara-Castro brings more than 30 years of journalism experience to ensure DatingAdvice articles have been edited for overall clarity, accuracy, and reader engagement. She has worked at The Atlanta Journal and Constitution, The Gwinnett Daily News, and The Gainesville Sun covering lifestyle topics.

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The Short Version:  Madison, Wisconsin, also known as Mad Town, is a hub of activity with thousands of residents enjoying the beaches, bike trails, restaurants, museums, and other engaging spots throughout the area. The capital city is a welcoming and diverse place in the Midwest, and exploring its many sights can help you bond with a date. As a starting point, we’ve highlighted six exciting date activities to add a little zest to the love lives of residents and visitors alike. From icy adventures to culinary sensations, this list is a sampling of the best activities Madison has to offer couples.

The Wisconsin State Capitol Building may not strike the casual observer as a particularly romantic spot, but, for politicos Kyle and Ashley, it was the perfect wedding venue. They had met there years earlier when they were working on the same political campaign. The couple put a political spin on their wedding, from the groom’s American flag socks to the custom campaign buttons commemorating their union, and it was pretty adorable from start to finish.

Their wedding photographer Kalli said she was humbled to be part of Kyle and Ashley’s special day. “To witness a love as great as theirs is the greatest gift of all,” she wrote in her blog.

Sandwiched between two lakes in Dane County, Madison, Wisconsin, has many unexpectedly romantic corners to enjoy with someone special. You don’t have to settle for the typical dinner-movie routine here.

If you’re looking to share a memorable night out with a date or spouse, Madison can offer you a sprawling city full of indoor and outdoor date activities.

Robert Gard, Director of Public Relations and Communications for Madison, told us the city is an engaging and affordable place to take a date any time of year. “People here are high energy, and that translates to dating,” he said. “You’re going to find something fun and entertaining to do when you go out with someone here.”

1. Go Ice Skating During a Popular Winter Festival

Madison’s winter season brings with it a flurry of excitement and fun. From ice fishing to ice kiting, a lot of unique winter activities give couples a reason to bundle up, brave the cold, and enjoy the snowy months. The town’s winter festivals often attract hundreds of city residents as well as visitors from across the state.

The Frozen Assets Festival, a February event on Lake Mendota, tempts residents with a lot of winter activities, including ice skating, sleigh rides, pond hockey, and snowshoeing. After you’ve spun around with your date on the ice (and maybe fallen into each other’s arms a few times), you can warm up with complimentary s’mores and hot cocoa.

Photo of a family at the Frozen Assets Festival

The Frozen Assets Festivals celebrates all the wintertime lakeside fun that Madison has to offer.

This weekend-long event also features performances and competitions to delight attendees of all ages. “We like to stay active in Madison no matter what the season,” Robert commented, “and a lot of our activities are centered around the lakes because they’re our biggest attraction.”

2. Dine on the Lake at the Edgewater Hotel Restaurant

Because of its picturesque location on the banks of Lake Mendota, the Edgewater Hotel is a hot spot for many locals seeking a good time. Its five-star restaurants are particularly popular. The Boathouse is a casual waterfront eatery with a menu full of classic Midwestern favorites, including brats, burgers, and cheese curds.

If you’re in the mood for more of an upscale place, you can head to the Statehouse, the hotel’s signature restaurant. The menu features house-made pasta dishes as well as mouth-watering Wisconsin fish fry.

Photos of Statehouse's dishes

From sizzling steaks to farm-fresh salads, the Statehouse menu has something for everyone.

Taking a date out to dinner is a tried-and-true way to bond by sharing a tasty experience, and Madison has a lot of fantastic local places to choose from.

Another dining establishment worth a stop is Graze, one of the city’s original farm-to-table restaurants. The head chef here, Tory Miller, recently competed against and beat Bobby Flay in an episode of “The Iron Chef Showdown.” If you want to impress a date, you can reserve a table at Graze and sample eclectic dishes with locally sourced ingredients.

“What’s great about Madison is you can go to an award-winning restaurant and have an affordable dinner,” said Robert. “We have a lot of very high-quality food options here.”

3. Rent a Kayak or Boat for Two

Madison’s lakes are a huge part of its recreational offerings, so you might as well take advantage of them by inviting your date to cruise along the water with you.

You can rent boats, kayaks, and other lake equipment by the hour at Brittingham Boats and then split a deluxe grilled cheese meal after you’ve spent a day exercising in the sun. In June, Brittingham Boats offers a Full Moon Paddle, which sounds awfully romantic to me. You can paddle around Monona Bay under a blanket of stars while a live band plays soft music. The event lasts from 8:30 p.m. to 11 p.m.

Photo of stand-up paddleboarding in Madison

Madison has 12 beaches open to the public throughout the summer months.

Whether you enjoy stand-up paddleboarding or volleyball, Madison’s sandy beaches can provide you with many diverting activities in the summertime. Plus, when you’ve had your fill of sunshine, you can cool off with a cold beer at the Biergarten at Olbrich Park.

4. Stroll Through an Art Museum & Have a Thoughtful Conversation

The Madison Museum of Contemporary Art has been wowing visitors since it opened in 1901. Its free exhibitions and programs provide plenty of opportunities to get involved in the local art community and broaden your horizons with someone special by your side.

At the museum, you can express your opinions, share ideas, and get to know someone on a deeper level by walking through these visually stunning galleries.

Screenshot of the Madison Museum of Contemporary Art's website

You can shake up your dating routine at the Madison Museum of Contemporary Art.

The Chazen Museum of Art is another popular museum with over 20,000 works of art on display. From ancient Greek sculptures to contemporary abstract paintings, the expansive four-story facility provides couples with thousands of conversation starters. The museum’s thought-provoking atmosphere is ideal for daters of all ages, and it’s also a budget-friendly alternative to sitting in a movie theater in silence.

After your trip to the museum, you can walk a bit to check out the local farmers market. Every Saturday from mid-April through early November on the Capitol Square, the Dane County Farmers Market is a must for foodies across town, and it offers a great opportunity to plan a home-cooked date night dinner for two. Robert described the bustling market day as “a fun way to get out and see all the colors and flavors of Madison.”

5. Immerse Yourself in Food-Related Events & Workshops

Madison packs its calendar with unforgettable events throughout the year. You can search its online calendar for out-of-the-box date ideas ranging from trivia nights to hockey games.

Robert recommended daters stop by State Line, a local distillery and cocktail lounge, to share a drink and maybe participate in a Cocktail Lab taught by some of the best bartenders in the city. The State Line offers this 90-minute class teaching people fun skills they can use at their home bars.

Screenshot from State Line's website

The State Line Distillery is known for its homegrown and handcrafted spirits.

You don’t have to look very far to find a good time in Madison. Every Labor Day weekend, the Taste of Madison event creates a lot of hustle and bustle in the Square as foodies flock to sample small plates from over 80 restaurants and watch 35 live musical performances. About 250,000 people came to the last event, and they gave it rave reviews.

“The variety of food was pretty impressive,” wrote Chloe O. in a Yelp review. “There were everything from cupcakes to Indonesian food.” Admission is free to all, so you have no excuse not to take a date to this jam-packed food-loving extravaganza.

“Moving around from venue to venue takes the pressure off a date,” Robert commented. “You can keep on the move and just relax into the date.”

6. Get Your Heart Pumping on Miles of Bike Paths in the City

Livability ranked Madison as one of the top 10 healthiest cities in the US because its residents take part in so many outdoor recreations, including biking down miles of trails. Madison actually has more bikes than cars because the city is so easy to traverse. In 2015, the League of American Bicyclists gave the city Platinum status, making it one of only four US cities to hold this honor. All in all, Madison is the Midwest’s unofficial biking capital, and it’s one of the best cities to take a bike, grab a date, and enjoy the fresh air. You can even take a biking food tour of the city’s stores, bakeries, and breweries. Yes, please!

Throughout the year, you’ll find thousands of people out exploring Madison’s 200+ miles of trails. “It’s a very active community,” Robert said. “It could be minus 10 degrees outside, and you’d still see people out biking and jogging.”

In Madison, Dating is Always an Adventure

In September 2016, on the floor of the Wisconsin State Capitol building, Kyle and Ashley said their vows while their guests sat at the desks of state representatives. The grandiose architecture and historical surrounding set a memorable scene for the couple’s big day, making their love story all the more romantic.

Throughout the Mad City, you can find plenty of opportunities to create a special moment with that special someone. Madison’s dating scene is as lively as are its residents. From paddleboating in the summer to ice skating in the winter, you can always find an activity to divert you and your date for an afternoon. Take our advice and head to Madison to discover new romantic places to eat, drink, bike, and be merry with a loved one.

“We’re a curious and adventurous lot here,” Robert said. “You won’t find people sticking to a routine — they’re more willing to go out and try a new restaurant or festival on a date night.”

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