“What are some great date night ideas in around Madison?!” It’s a question we get asked a lot.
So we put some time and energy into polling the audience (aka you ladies), did some research, a lot of googling, and reached out to some friends who just happen to know the Madison food scene quite well. And we put together, what we think, is an AMAZING round up for you all!
Most of these dates ideas are specific to Madison, but definitely not all of them. Even the Madison specific ones can serve as inspiration for date night ideas to do where you live! They could also be things to do with friends or other couples. Our goal is to help you get out and live life again with the people you love. That being said, here are our top 26 (yes, 26!!) ideas!
26 Madison Date Night Ideas:
1. Devil’s Lake and Wollersheim Winery or Vintage Brewing Company
Hike Devil’s Lake. Devil’s Lake State Park hours are 6 am to 11 pm seven days a week and you will need a state park admission sticker! Annual admission stickers cost $28 for Wisconsin residents or $38 for non-residents. Daily pass rates vary from park to park. At Devil’s Lake State Park Daily Rates are currently $13 for residents or $16 for non-residents. You can buy passes at the park or do it online here.
One popular hike at Devil’s Lake is hiking the circumference of the lake. It’s a flat, scenic 3 mile hike that only takes a couple of hours and that most visitors can do without being overly athletic. If you are up for a bit more of a challenge, we hands down recommend hiking the East Bluff Trail. If you are concerned about stairs or the elevation, then hike the Tumbled Rocks Trail along Devil’s Lake’s western shore.
After hiking, stop at either Wollersheim Winery & Distillery (open 12 pm- 5pm) for a much deserved drink and enjoy a picnic or eat at their Bistro, open 12-4:30 pm Thursday to Monday. Or head the Vintage Brewing Company in Sauk City for a drink and dinner overlooking the Wisconsin River. And you guys… they allow dogs on the patio and even have a dog MENU! What?! Hike with your pup and then grab dinner. WE LOVE IT!
2. Downtown Middleton and Drinks
Every time we are downtown Middleton, whether it be for a photo shoot or grabbing coffee at Grace Coffee Co., we always talk about how cute it is! Check out the adorable stores in downtown Middleton and grab a drink at either Longtable or Grape Water. Longtable has an amazing selection of beers (300 brews!!). They also have a full menu and plenty of gluten free options! Grape Water is also an awesome option and has a great selection of wine and appetizers including local cheeses. If you are in the mood for a great appetizer, head to Free House Pub in Middleton and try the charred carrots. They are TO DIE FOR!
*Twist: Pick out a drink for your date to make it even a bit more fun!
3. Try Something NEW!
Pick a new restaurant with food that you’ve never tried! Sushi? Oysters? Pho? Give something new a go!
*Twist: Pick something and then give your date clues and make them guess where you are going!
4. Appetizer Hopping
This is a date that has been on our list for quite a while and we just need to make it happen! We both think it sounds like so much fun and such a great way to try a few different places!
Here is how it works… go downtown and “hop” from restaurant to restaurant ordering an appetizer and drink at each spot. After four or five places, you are sure to be full… and possibly a little drunk. 😉 Maybe drink a glass of water at every other place. Ha! This would be a super fun date night with other couples, especially in the summer with all of the outdoor seating downtown.
Our favorite Madison patio dining includes – Lucille, Camp Trippalindee, Cafe Hollander at Hilldale, Nineteen09 in Cross Plains, bartaco, The Boathouse at the Edgewater, and Pinkney Patio at Settledown Tavern to name a few!
5. Observatory Hill and the Union
Melissa and her family did this last summer and it was so fun!! Order take out from your favorite restaurant or pack a picnic and eat on Observatory Hill (Observatory Dr.) on campus. Don’t forget to pack a blanket. Then toss everything back in your car, and walk the Lakeshore Trail, which has easy access from Observatory Hill. Head to the Union to get Babcock Dairy ice cream at the Daily Scoop and/or drinks and enjoy them down by the water on Lake Mendota!
There are tons of food and beverage options at the Memorial Union, including a brand new restaurant, the Sunset Lounge & Outdoor Restaurant which serves sharables, pizza, dessert, craft cocktails, local beer, select wine, and premium mixers.
6. Cooking Class at Sur La Table
You know we love a good cooking class! 😉 Take your date to a cooking class at Sur La Table at the Hilldale location. They offer in store classes, online classes, and also do private events. These cooking classes are taught by professional chefs and teach cooking techniques that you’ll be able to use in your at home cooking! They currently have openings for a variety of classes and the menus look absolutely amazing… Surf and Turf, Crab Cakes, Rustic Italian Cooking, Korean BBQ, French desserts. Yes, please!
7. Shopping Date
Katie and Logan usually do this on their birthdays. They take off work and go on a ‘Shopping Date.’ Decide on a certain amount of money that you can each spend and go shopping in person! We purchase so much online these days, that sometimes we forget how much fun shopping in person is! The rule is you just have to love it, not need it. Hilldale is an awesome spot for shopping and then grabbing some food/coffee/drinks in between! Katie usually makes a visit to the lululemon store that day to buy her annual pair of overpriced leggings. 😉 Your birthday is a great excuse to splurge a little.
8. Homemade Fondue Night
When I dip, you dip, we dip! 😉 (Sorry, we had to…)
Send the kids off to a friend’s or grandparents’ house and do a fondue night. Logan and Katie have been doing this for years. It was a family tradition of Logan’s growing up and now it’s a fun tradition of theirs. They actually found not one, but TWO vintage electric fondue sets on eBay so they can have more people join in the fun. Surprisingly, they don’t do cheese or chocolate – they do broth and peanut oil. They dip (cook) chicken, steak, shrimp, brussel sprouts, pearl onions, small potatoes, and mushrooms. And they always have a large variety of dipping sauces like Honey mustard, cocktail sauce, steak sauce, honey, and (Katie’s absolute favorite) sour cream and horseradish sauce.
If vintage flair isn’t your thing, here is the fondue set that Melissa has and loves. You could even order one and surprise your partner with this fun date night idea! Here are some fondue recipes to get you started.
Twist: Invite one to two other couples to join you (any more than that and there gets to be too many sticks in the pot and takes a really long time and people’s dippers start falling off the skewers) and have each couple bring a few things to dip. Take it to another level by giving your date night a 60s theme. Dress the part and have fun! Also, fondue is a marathon and not a sprint. It takes some time, but allows for fun conversation!
9. Move it!
This could be anything you want it to be, but it has to be an activity. Here are some of our ideas. Try rock climbing at Boulders. Rent a paddle board, kayak, canoe, paddle boat, etc. through Madison Boats. Take sailing lessons through Hoofer Sailing Club. Go mini golfing at Vitense. Go to a driving range and hit balls. Try axe throwing at Happy Axe or Flannel Jax. Or during winter months, go snowboarding, skiing or tubing at Tyrol Basin! As parents, I think we are used to standing back and watching our kids have all the fun. Get out there and do it yourself!
10. Trivia Night
We love this idea – such a fun way to work together with your date and even a group of friends! World of Beer in Middleton is currently doing trivia night every Tuesday and Thursday! So grab some food, drinks, and see what you know… or don’t know! The Boathouse Bar & Grill also does trivia night from time to time and we hear it’s an absolute blast!
11. Pick an Adventure Group Date
A coworker of Katie’s used to do this with all the women in her family every single year, but it could absolutely be applied to group date with a few of your fun couple friends! Here is how it works:
Decide on how many couples want to be involved.. anywhere from 3-5 couples is probably good. Throughout the year, each couple plans a super fun day date. (It could also be night. Heck, it could even be a weekend getaway if that’s what you all decide.) The day has to be a complete surprise to all the other couples and a kind of out-of-the-ordinary kind of day. For an example: Goat yoga, a craft cocktail class, and then a dinner boat cruise where you play drag queen bingo! LOL Ok, so it doesn’t have to be that crazy, but you get the point. All you are able to tell the other couples is what to wear and you will probably want to decide on a budget beforehand. The rest could be anything and everything! There are endless possibilities!
12. Pizza Farm
Take your date and grab a wood-fired pizza at Sprouting Acres Farm near Cambridge! They are open every Sunday from noon – 8 pm for the remainder of the summer. We love the idea of experiencing wood-fired pizza and maybe a bottle of wine (bring your own!) on a farm. This would make a fun family date too! Bring a blanket, some cards, and even a game to make a night out of it!
13. Bloom and Trader Joes
Ok, this isn’t technically a date night, but this one is right up our alley. We’ve actually both done this with our husbands and have even done it together. M&K date! (Ha!) Grab a breakfast sandwich from Bloom, find a bench, or take a walk down Monroe Street (one of our favorite spots), and then go shopping at Trader Joe’s. There is just something about shopping at TJ’s that’s so fun! We love trying all of their fun seasonal products and we always grab a few bottles of wine and beer to try!
Twist: Try something unique/something you’d normally never buy and try it just for fun!
Another really fun place to check out on Monroe Street is Orange Tree Imports – especially if you are a foodie or just really enjoy cooking!
14. Parade of Homes
The Parade of Homes is over now in Madison for this year, but this is one of our favorite date nights. Grab tickets to POH and then plan out brewery/winery and food stops along the way! Here is a post that Katie wrote for Buell Real Estate that gives a rundown of wineries and breweries around the parade sites! If you want to see a little bit of what it’s like, we both went this year and we have a highlight saved on our Instagram page. The homes were absolutely mind-blowing! We always go to the really fancy/expensive ones. What can we say, we love to be WOWED by homes we may never be able to afford! Haha!
15. Fridays on the Farm
Vitruvian Farms, (we love EVERYTHING this farm stands for!!) located in McFarland is a sustainable, certified organic, local farm that focuses on growing and selling food within a 15 mile radius. Fresh produce on average travels 1,500 miles. That’s crazy!! So how does this fit into a date night idea? Most Fridays, they offer fun options like a farm tour, music, and games! Bring a picnic, grab some fresh produce.. sounds like fun to us! Here is a list of upcoming dates and what they have going on.
16. Live Music
Bob Marley said it best when he said “One good thing about music, when it hits you, you feel no pain.” There is just something about live music. It’s good for the soul. We would be here all day if we listed off all of the places you can find live music, so we will just name a few.
Lone Girl Brewing Company has live music on their rooftop every Friday from 7:30 – 10:00 pm and every Sunday from 2:00-4:00. Pick a nice night, grab a drink, and enjoy some live music! Here is the calendar of upcoming events!
Buck and Honey’s has three great locations around Madison and a fantastic live music line up at each one: Sun Prairie | Monona | Waunakee. The Monona location overlooks the Yahara River and Monona Park and features 23 boat slips, so it’s a fabulous place to stop if you are out on the boat!
17. Madison Eats Food Tours
Madison Eats Food Tours give you a taste of Madison, Wisconsin’s incredible food scene through walking and biking restaurant tours and culinary events. They partner exclusively with locally owned businesses, ensuring that your ticket purchase helps our city thrive! Madison Eats is locally owned and operated, with award-winning local food writer Otehlia Cassidy at the helm.
Otehlia started Madison Eats back in 2012. The tours last about 3 hours and stop at 5-6 restaurants. Madison Eats is deeply committed to supporting Madison’s local food economy. They have grown to offer walking restaurant tours, bicycling brunch tours, private tours, bachelorette party outings, large group events, custom tours, market tours, and more! This would be such a fun date night!
18. Wisconsin Brewing Company
Located just south of Verona, Wisconsin Brewing Company has beer, seltzer, and non-alcoholic beverages. They have great space, have live music (dates here – scroll down), and suggest ordering in food from a local restaurant to eat while you’re there. A few great options that are right across the street are Sugar River Pizza Company, El Charo Mexican Grill, and North & South Seafood and Smokehouse. All of these tried, true and highly recommended!
A beautiful summer evening at Wisconsin Brewing Company would make an awesome date! The scenery is beautiful (it feels like you are in the country) and they even welcome pets (on leashes)!! They have fire pits, an outdoor bar and seating, yard games and more! One of Katie’s family traditions is going to their pumpkin chucking event each fall.
19. Dance Lessons
Take a dance lesson with your partner! Every Tuesday, the Brink Lounge offers Bachata dance lessons at 7:30 and then has a Tango/Salsa dance night after, starting at 8:30! Melissa took salsa lessons when she was in Spain and loved it so much. It would be a lot of fun to do with a partner or a group of friends! Fred Astaire, which features ballroom dance, also offers lessons and includes a variety of dances! This would be an awesome way to practice a dance for a wedding or special event too!
20. Thrifting
This one has two parts… or options you could call them!
The first one would be to just go thrift shop together! Not everyone loves it, but if you are a thrifter, you know the love runs deep! Logan and Katie LOVE a good flea market! Their favorite is the Elkhorn Flea Market. Katie actually wrote a two part blog post on it back in 2013 when she has her own personal hobby blog. There is just something about treasure hunting and price bartering that makes her happy! You can find some of the most interesting and uniqe things for your home at a flea market or thrift shop!
Ok, option two may be the craziest option, but it’s also pretty darn fun! Have a Saint Vinny’s party with a few other couples or friends. You and your significant other have a budget of $15-20 (or whatever you want it to be). Head to a thrift store like Goodwill or St. Vinny’s and use your money to buy the other person an outfit for the evening! Then have a dinner party at one of your houses or, better yet, go out in your crazy outfits! We talked about this date and we decided this was definitely a group date sort of thing. There is comfort in numbers! Haha!
21. Bootcamp & Coffee
Again, not for everyone, but this might be one of Katie’s top three picks for date ideas. She loves to workout and LOVES trying new things. If you and your partner are both on the workout train these days, this might be an idea date for you guys too! She has done this with girlfriends many times, but will probably not be doing this with Logan any time soon. He does not share the same passion for sweating like crazy and almost dying, so he might pass on this idea. Buuuuut if you and your significant other are both in, try a new fitness class (most have a complimentary first class) and hit up your favorite coffee/brunch spot. A few of our favorite coffee shops are Barriques on Monroe Street, N+1 in Verona, and Grace Coffee Shop in Middleton.
22. Shooting Range & Supper Club
This is like the ultimate mid-western date night! Also, we fully understand this is NOT for everyone. If target practice is your thing or something you think might be fun, give this a go! There are a few ranges around Madison: Deerfield, McFarland, Sun Prairie, Waunakee, and Oregon. We also have some of the best supper clubs in and around the Madison area. Some of our favorites are Ishnala (a little drive), The Old Fashioned, Kavanaugh’s Esquire Club, and Smoky’s Club.
Want even more info on this Mid-western tradition? Check this How to Supper Club post by Destination Madison.
23. Murder Mystery or Theme Party
A murder mystery party is a themed event where attendees dress up to match an era or a genre. They will then work together to solve a fictitious murder which occurs during the party. It’s like a live-action version of the game Clue!
Katie had been to one of these parties and LOVED it! It was a 1920s theme and absolute blast to receive my character assignment, dress the part, and spend the night drinking and acting! Seriously, it was so fun!
Here is the rundown to exactly how to throw a murder mystery party and there are so many fun themes to pick from : Poolside Murder, Bloodwood Masquerade , Murder at the Luau and so many more! The whole site it very easy to navigate and the cost of a party plan is only $40-$50, so super affordable!
24. Cook an International Meal at Home
As you all know, we actually enjoy cooking, but it’s not every day that you have the luxury of time to prepare an amazing and elaborate meal. Our suggestion here would be to slow down and enjoy the process of cooking. Plan a meal that sounds amazing to you both, go shopping for the ingredients together, go home, pour some wine, turn on some music, and start cooking. Sit down and enjoy the meal just the two of you.
Here are a list of ethnic grocery stores around Madison, Wisconsin.
25. Take a Craft Cocktail Class
Gib’s is a craft cocktail bar that is a built into a two-story victorian house in the Willy Street neighborhood. Offering a charming, relaxing environment to enjoy a drink and conversation with friends. Food is available from our neighbors at Grampa’s Pizzeria and craft cocktail classes are available for groups of 8 or more! Fill out this form if you are interested and someone will get back to you about booking your event!
26. Comedy Club
This is such a fun date to do with just your significant other or in a group! Katie and Logan have seen several shows at Comedy on State and they are always a blast. There is a 2-beverage minimum (alcohol and non-alcohol beverages are served), so if you are not a big drinker, save your cocktails for the show. Also, they do not serve food, so dinner beforehand is always fun! A few recommendations for restaurants near by are Cento, The Coopers Tavern and Fresco. Fresco has amazing rooftop dining!
That’s a WRAP on Madison date night ideas!
This Madison date night ideas roundup was definitely a labor of love, but we hope you all have found this helpful and will try some of these. This was also a really fun date (over) night! If you do end up trying them, we would love for you to tag us or share a picture with us.
