Kids, this is the story of how I met your mother, and it was all thanks to 608today. Okay, so maybe that’s not exactly how the 2000s sitcom went, but if Ted Mosby had consulted us for date night ideas, we could’ve shaved the show down to two seasons (and saved his kids a lot of time). Whether you’ve met “the one” or are hoping to impress someone new, we’ve got plenty of local date night ideas that are legen — wait for it — dary.
A night out on the town
East Washington Avenue
Tickets are now on sale for Forward Madison FC’s upcoming 2024 season. Catch a game before heading to the Robina Courtyard for dinner and drinks. Then, enjoy a night of friendly competition at the Aftershock Arcade.
Capitol Square
Take a free tour of the State Capitol and chat about what you learned over chips and queso at Canteen. Round it all off with an early evening show at the Overture Center. With everything in such close proximity, you can spend less time finding parking and more time flirting. Don’t want the date to end? Check out Tornado Room’s late-night menu.
Willy Street
Start with dinner at the Weary Traveler, and grab a drink at Crystal Corner before catching a show at Cafe CODA.
The way to the heart is through the stomach
Mint Mark, 1929 Winnebago St. (moving soon to The Standard)
This eatery serves up small plates that are great for sharing. This makes for an engaging meal full of food-centric conversation starters and even better meal starters — try the biscuits.
Harvey House, 644 W. Washington Ave.
Impress your date with a meal at one of New York Times’ top 50 restaurants in America. Customize the experience by indicating on your reservation whether you’d like to sit at the bar, in the main dining room, or in the more private upstairs dining area.
Turn KeySupper Club, 1344 E. Washington Ave.
If you like Settle Down Tavern, you’ll love its elevated sister restaurant. The Thursday date night special costs $60 and includes a salad, two entrees, dessert, and a bottle of wine.
Some friendly competition could make or break your date. | Photo via Turnkey
Lallande, 1859 Monroe St.
This bistro offers a cozily romantic ambiance and a seasonal menu that is sure to impress self-proclaimed foodies.
Play games (just not with your heart)
NerdHaven, 203 Cottage Grove Rd.
Great for double dates, this arcade is home to one of the state’s largest collections of pinball machines in addition to over 150 arcade games.
Blind Shot Social Club, 177 South Fair Oaks Ave.
You don’t have to be a golf pro to have fun at Blind Shot. Reserve a golf simulator to play mini-games, or sit at the bar and try your luck at the indoor putting green.
Roll Play, 3241 Garver Green, Ste. 115
If your date likes bubble tea, board games, or craft beer this is the place to be. This casual board game cafe serves up Asian-inspired handhelds and hosts a variety of themed trivia and game nights.
Madison Axe, 2427 S. Stoughton Rd.
Fingers crossed the night goes well, since your date will be wielding an axe.
If you’re really hoping that it works out
Lake Loop, Around Lake Monona
This 13-mile trip gives you plenty of time to chat with your date and enjoy local scenery. Pro tip: Take a pit stop at the Olbrich Biergarten or Monona Bait and Ice Cream Shop for a mid-ride pick-me-up.
Pickleball, Various locations
Madisonians are no strangers to the art of pickleball. If all goes well, you and your boo can join a local pickleball league to ensure some recurring date nights.
Boulders, 129 S. Carroll St.
What better way to practice trust in your budding romance than by relying on your other half to spot you as you traverse the rock-climbing wall? Be sure to get an orientation session if anyone in your party is a newbie.
During the warmer months
Governors Island, 2 Governors Island Pkwy.
Think: Picnic Point, but less busy. This 3/4-mile paved hiking path offers a view of the isthmus from the north shore of Lake Mendota.
Marshall Boats, 2101 Allen Blvd., Middleton
Rent a tandem kayak this summer and paddle into the sunset with your date. If you really want to get cheesy, opt for the swan paddle boat over at Wingra Boats.
Allen Centennial Garden, 620 Babcock Dr.
While strolling through this outdoor garden tucked away on the north side of campus, you’ll forget you’re just minutes away from the heart of downtown. Love can still bloom in the winter months, but you’ll have to head over to Olbrich’s indoor conservatory to see living flora.
If you want an “old fashioned”-style date
The Old Fashioned, 23 N. Pinckney St.
It doesn’t get more old fashioned than drinking an old fashioned at The Old Fashioned.
Monty’s Blue Plate Diner, 2089 Atwood Ave.
Transport yourself to the 1950s at this diner that’s known for its ample vegan options and stellar dessert menu. Order one milkshake with two straws to have your own “No Strings Attached” moment.
Vitense Golfland, 5501 Schroeder Rd.
Mini-golf is as classic of a date as they come. Cold outside? No worries, you can choose from the indoor or outdoor mini-golf course.
If you wanna show off by knowing all the hottest events in town
- Shameless plug: Sign up for our daily newsletter, where we call out our top picks of things to do around town. Your date doesn’t have to know we’re behind it, you can take all the credit.
- Stay up-to-date on the coolest local events around Madison with our events page (and check out this guide for our tips on navigating the page).
