The Scoop: Madison is the second largest city in Wisconsin by population with over 255,000 people choosing to live between Lake Monona and Lake Mendota. The city has its fair share of attractions to entice couples, and 2019 may just be its biggest year yet in terms of trendy entertainment and engaging activities. We’ve listed some of our favorite modern date ideas to get Madisonians to go out and have a fantastic time with their significant others.

When I was young, I imagined dating life would be full of fun, drama, and excitement. I imagined riding into the sunset alongside some dark and dashing figure. Then I got older and found myself on a carousel that went round and round without quite reaching the sunset. I went on dates and had the same conversations over the same bowl of pasta, and it wasn’t nearly as exciting as I’d thought it would be.

Even for hopeless romantics like myself, dating can become a tired routine if it means going to the same restaurants and bars (or just staying at home) week after week. That doesn’t have to be your fate, though — especially if you live in that mad town known as Madison, Wisconsin.

You can find excitement on the water and at the theater and throughout this culturally vibrant hub. We’ve come up with eight reasons to drop the routine and make a romantic date in Madison. The resources on this list can get you unstuck from that rut, so let’s get to it.

1. Essential Madison Experiences™ Offers Adventure

First of all, we have to point out an exciting opportunity to savor the sights, sounds, and tastes of Madison through Essential Madison Experiences. These eye-opening experiences got started in 2018 and have taken off because residents enjoy seeing familiar sights in a completely new way.

For instance, the National Mustard Museum opened its doors for a mustard bites tasting and educational presentation that delighted visitors, even those who weren’t all that fond of mustard. This is just one of many unique experiences offered by the city.

Anna Shircel, the PR & Communications Coordinator for the Greater Madison Convention & Visitors Bureau, said the Essential Madison Experience offers something a little outside-the-ordinary for daters seeking an adventure in the city. “We’re giving people a different view of an attraction they know and love already.”

2. Capital City Food Tours Invite Discussion

Capital City Food Tours offers a fun exploration of Madison’s favorite eateries and bars. You can spend two to three hours walking from restaurant to restaurant and savoring delicious bites or specialty drinks.

The Stroll Down State Tour is one of the most popular options. The two-mile walking tour starts at the Library Mall and includes two food tastings and a shopping excursion on State Street. The tour starts at 2 p.m., rain or shine, and tickets cost $45 per adult.

According to the website, “Our goal at Capital City Food Tours is to provide all of our guests with an enjoyable afternoon eating, drinking, and shopping while learning about the history and lifestyle of Madison.”

3. Botanical Gardens Provide Tranquility & Fresh Cocktails

The city’s Olbrich Botanical Gardens is a popular destination during the winter months because the conservatory maintains a temperature of about 70 degrees to protect the plants from the seasons. You can stop by to warm up, escape the blustering snows, and enjoy a tropical atmosphere.

Strolling through the 16-acre outdoor gardens can be a romantic activity during the summer time. Admission to the outdoor gardens is free (donations are appreciated), and the Bolz Conservatory has a $2 admission price, making this beautiful place an affordable alternative to the traditional dinner-and-a-movie date.

Photo of a couple at a botanical garden in Madison

The Olbrich sometimes offers specialty cocktails made with fresh herbs from the gardens.

The conservatory has also put on social events and cocktail hours to bring in a crowd in the evening hours. The Olbrich’s calendar of events can keep you up to date with everything going on throughout the year.

4. Popular Distilleries Have Won Locals Over

The newly opened State Line Distillery has become a popular hangout for singles and couples in Madison.  This local distillery invites patrons to settle in with a cold brew or craft cocktails and enjoy each other’s company. These mixologists pride themselves on using the freshest ingredients in drinks that pack a punch.

The Dancing Goat Distillery is another trendy date-night option with spirits galore. Head Goat Travis Hasse created his first Apple Pie Liqueur in 2008, and he has been running with those sweet flavors ever since. Couples can try a cheery cherry pie drink or take a tour of the tasting room to see how every batch of indulgent liqueur is made.

“You can get out of the house and be together,” Anna said, “and that’s never a bad thing.”

5. A New Performing Arts Venue Sells Out Every Night

The Sylvee is a dynamic performing arts theater where over 2,500 music lovers can gather for a concert or show. The Frank Family named this theater after Sylvia Frank, who raised her children to love rock’n’roll.

Screenshot from the Sylvee's website

The Sylvee electrifies a crowd with its unforgettable concerts and live performances.

Over the years, this family-run production company has brought big-name talents, including The Rolling Stones and U2, to Madison in sold-out performances. Now the Sylvee has opened its doors to continue the musical tradition and rock the local music scene. Heading to a concert here would be a thrilling date-night activity.

6. Mad Hotel Week Entices Visitors With Stellar Discounts

Thinking of making a special trip to Madison? Consider stopping by for Valentine’s Day to save some money and enjoy a relaxing time in the snow-covered city. Madison offers a special deal, known as Madison Hotel Week, to people booking a stay during Valentine’s Day week.

Not only do participating hotels drop their prices during this week, but they also sweeten the deal with extra savings around town. Madison Hotel Week visitors receive a coupon booklet upon check-in and can browse exclusive offers at 19 local restaurants, all of which are part of the Food Fight Restaurant Group. These deals are only valid during the Hotel Week, which runs from February 8th to the 18th next year.

“If you’re thinking about visiting Madison, this is a good time to do it,” Anna concluded.

7. A Holiday Bar Warms the Heart in Winter Months

Every December, Lucille on King Street puts up bright, over-the-top holiday decorations to wow visitors from all walks of life. As if the twinkling lights, wreaths, and mistletoe covering every square-inch of the pizzeria weren’t enough, Lucille also brings some holiday cheer to its menu by adding a large selection of winter cocktails.

Photo of the Lucille

In December, Lucille turns into a boozy North Pole that serves holiday drinks inspired by the season.

You and your date can get a Nice Shot (rum, peppermint, and chocolate) and a Naughty Shot (bourbon and cinnamon) to kick things off, and then warm up with a steaming cup of Bad Santa milk punch, which is served in a cup shaped like Santa’s pants and boots.

It’s no wonder people call Lucille “the Miracle on King Street.” Its fun decor and inventive drinks give couples something to look forward to during the frigid Wisconsin winter. You can get into the holiday spirit and find other Miracle pop-up bars here.

8. And It’s a Beautiful Wedding Destination

Madison has many romantic venues where couples can book a classy indoor or outdoor wedding. Quivey’s Grove is a popular springtime choice because of its green fields, wildflower bushes, and canopy of black walnut trees. A white tent can protect guests from rainy weather, and the space can comfortably fit up to 225 people. This wedding venue currently has a four-star rating on the Knot.

In the heart of downtown Madison, the Overture Center for the Arts is perfect for couples seeking an elegant and trendy space for their big day. The sweeping ballrooms, lounges, and terraces at this venue all offer an upscale atmosphere complete with chandeliers and state-of-the-art sound equipment.

The Overture’s event calendar fills up fast, so contact [email protected] ASAP to reserve your dates for 2019.

“Can I give them a higher rating than five stars?” one bride asked in her review. “They helped make our wedding what it was. The venue is beautiful, and they do everything they can to make your day easy and stress-free.”

“Mad Town” Has Attractions to Delight Residents & Visitors

From its natural lakes to its trendy bars, Madison has everything you need to have a great time if you only know where to look. You can explore the sights alongside your partner in crime and shake up your dating routine with a craft cocktail, culinary tasting, live performance, or another special experience.

Your love life can be every bit as exciting as you want it to be, but it takes effort to go outside your comfort zone and find those fantastic places where your imagination can run wild. Madison has many options to tempt anyone seeking a romantic getaway in the heart of the Midwest.

“You can get away with your loved one,” Anna said, “and make great memories by doing something hands-on together.”