26 Creative Date Ideas in & Around Madison, Wisconsin

Racking your brain for the perfect thing to do around Madison?

Here are some fun, mostly outdoor excursion ideas. Whether you’re looking for something unique to do with visitors, want to mix it up with friends or family, or are planning a romantic surprise, we hope this list gives you some inspiration!

Free (or Almost Free)

Bike on a Classic Madison Trail

Madison has consistently made it onto lists of best cycling cities in the US, so why not enjoy one of the city’s nicest features?

Some of our favorite routes include:

Don’t have a bike? You can check out a helmet and get a BCycle Bike Pass from any Madison Public Library location if you’re over 18 and have a library card.

📍 Where to start? Choose your own adventure! You can refer to Dane County’s interactive bike map for guidance.

🔗 Here’s some more information about cycling in the Madison area.

Catch a Movie at UW Cinemateque

Enjoying a free film on the University of Wisconsin-Madison campus comes highly recommended. International films and classic cinematic masterpieces feature heavily in the lineup at the screening facility of the Wisconsin Center for Film and Theater Research.

If you want to do the classic dinner and a movie thing, we recommend grabbing a huge and delicious Peruvian meal at nearby Estación Inka or loading up on uniquely topped pizza slices at Ian’s. (We realize this won’t keep the experience free, but trust us, it’ll be worth it.)

A disclaimer: we actually haven’t gone to Cinemateque yet! (It’s not for lack of trying … as we learned when we showed up just a few minutes too late, Cinemateque has limited seating and is first-come, first served. Doors open 30 minutes before showtime, so be sure to grab a spot early!)

📍 821 University Ave, 4070 Vilas Hall (Fourth Floor)

🔗 Read more and see the film lineup!

Go Birding in the Arboretum

Cranes and turkeys and owls, oh my! The UW-Madison Arboretum’s 17 miles of trails are teeming with more than 200 species of birds. You’ll have the chance to take in views of Lake Wingra and explore the adjacent wetlands, prairies, and deciduous forests as you keep your senses sharpened.

As always, the Madison Public Library system comes in clutch here. You can check out a backpack with binoculars and birding guides at every library location.

(And a bonus recommendation: If you are the birding type, you’ll LOVE the International Crane Foundation in Baraboo, just a 45-minute drive from Madison.)

📍1207 Seminole Highway (main entrance); you can enter the Arb from the east or west and park at a handful of locations throughout the area

🔗 Plan your visit to the Arb!

Go Foraging

Turn a hike into a quest by searching for edible plants and mushrooms! Foraging is allowed in the Dane County Park system as long as it’s not commercial and it’s for personal use, so pick your park and sharpen your senses.

⚠️ Of course, we’re including our typical disclaimer here: Be sure you’re absolutely confident in what you pick and consume. Consult a guidebook and/or an expert if you’re trying to learn more!

Organizations like the Madison Mycological Society have helpful information about mushroom hunting and offer foray opportunities throughout the year. The UW-Arboretum also has events and educational resources to help you hone your plant and fungi ID skills. (Just note that foraging in the Arb isn’t allowed.)

📍 See which Dane County Parks list foraging as an activity.

🔗 Read about some of the wild edibles you can look for—and learn where to find Dane County’s Community Orchards!

➡️ Check out our guide to the Golden Oyster Mushroom!

Have a Bonfire at Picnic Point

Picnic Point is a classic hike, but if you’d like to linger on this scenic Lake Mendota peninsula, you can rent a fire circle, grab your s’mores fixings, and settle in for the evening.

There are six fire circles spread out along the peninsula, most with cooking grills and each with seating for various group sizes. The walk to the furthest one is about 0.75 miles and has a capacity of 80 people! The others accommodate between 15 and 30 people and may be more your speed if you’re planning a quieter gathering.

Fill out this form at least three days in advance of your desired bonfire evening.

📍2000 University Bay Drive (main entrance; parking lot is nearby)

🔗 Visit the Lakeshore Nature Preserve site for more information.

Hike at Ferry Bluff

Ferry Bluff Viewpoint

This is one of our favorite scenic hikes near Madison, and the drive there is also lovely. It’s not a long walk up to Ferry Bluff, but you’ll definitely get some vert in. Stick around at the top with a picnic lunch or sketchbook and enjoy the scenery. You can also continue past Ferry Bluff to Cactus Bluff for even better sweeping views of the Mississippi River.

This area is closed December 1 through March 31 to protect roosting eagles, so be sure to plan accordingly!

📍 E9974 WI-60 Trunk, Sauk City, WI

🔗 Read what the DNR has to say about this State Natural Area.

➡️ Read about our 13 favorite hikes in and around Madison.

Learn to Curl

Have a blast, try something new, and make a bit of a fool out of yourself on the ice! From around November to March, many local curling clubs offer free or inexpensive learn to curl events, or you can attend a bonspiel (a curling match) for free. Madison Curling Club often has a long waitlist, but there are a handful of other clubs in the area, too.

📍 Madison Curling Club — 4802 Marsh Rd., McFarland; Blackhawk Curling Club — 1400 Craig Ave, Janesville; Alpine Curling Club — 1319 31st Ave., Monroe

🔗 See a map of curling clubs in the US and learn more.

➡️ Read our beginner’s guide to curling here!

Rent a Telescope and Stargaze

Did you know that members of the public can rent a telescope from Madison Metropolitan School District between September and June? Fill out a loan request form and you’ll get a confirmation email and instructions about how to arrange your telescope pickup. Rentals are for two weeks so you’ll have plenty of time to marvel at the night sky.

📍Stargaze at Brigham County Park (3160 County Highway F, Blue Mounds) or Donald Park (1945 WI-92 Trunk, Mount Horeb) for reduced light pollution.

🔗 Learn more about Madison Planetarium.

Visit the National Mustard Museum

Fun fact: Middleton is home to the world’s largest mustard collection, and you can admire over 6,000 jars of the condiment—and related memorabilia—for free! The National Mustard Museum isn’t huge, but it’s a great spot to visit when you’re looking to shake up your routine. (And the gift shop has the types of specialty items that make great presents for just about anyone.)

📍7477 Hubbard Ave, Middleton

🔗 Visit the Mustard Museum’s website for all the deets you could hope for, and to admire the latest World-Wide Mustard Competition winners. 😉

➡️ Are you a fan of the Mustard Museum? You might like these quirky Madison-area events!

Watch a Waterskiing Show

It was such a delightful surprise to stumble upon the Mad-City Ski Team’s show on Lake Wingra for the first time. Music blasted while athletes in neon lycra costumes formed human pyramids, leapt high into the air, and entertained the masses huddled on the shore on blankets.

Since then, we’ve made a point of hopping on our bikes with a picnic blanket and refreshments to take in this classic weekend event.

The team holds a free water ski performance for the public every Sunday evening at 6 PM between Memorial Day and Labor Day. Sometimes there are junior shows that start at 5:15 PM.

📍Law Park, 419 South Blair Street

🔗 Learn all about the team (and how to attend learn to ski clinics!!) here.

$

Canoe the Wisconsin River

This is one of our favorite summer day trips! Canoe a relaxed 10 miles down the wide and meandering Wisconsin River, stopping on pristine sandbars to stretch, have a picnic, or take a dip. (Alternatively, you can arrange for a longer trip and camp on a sandbar if you’d like to be out on the water for longer.)

We’ve rented our watercraft from Wisconsin Canoe Co., which offers a shuttle to support day trips from Arena to Spring Green (~3.5-4 hours) or overnight options beginning in Prairie Du Sac, Mazomanie, or Arena.

📍All shuttles depart from Peck’s Landing, S13608, WI-23, Spring Green

🔗 Get the scoop on how to prepare for your trip and read up on current paddling conditions.

Climb at Boulders

Hit up the climbing gym and challenge yourself in a space that’s accommodating to all experience levels. Even if you’re totally new to bouldering (minimalist climbing without ropes), you’ll find routes that help you build your confidence as you learn how to safely fall onto the thick mat below.

If you’re hungry after all that climbing, we recommend getting tacos and margaritas at Canteen, which is right down the street. Arrive on the earlier side to grab a seat and take advantage of happy hour!

📍129 South Carroll Street

🔗 Read more about Boulders.

Do the Dane County Farmers’ Market Challenge

Visiting Capitol Square on Saturdays for the farmers’ market—the largest producers-only market in the country—is a classic experience. Mix up your next visit with a fun challenge! Here are a few possible ways to play:

  • Pick a random number between 1 and 20. Then, moving counter-clockwise (because that’s the unspoken guideline for the flow of traffic around the Square), count each stall, stopping at the number you selected. You must buy one thing from that particular stall. Repeat as many times as you please, then prepare a meal using the ingredients.
  • Determine what your budget is or pick a set number of ingredients, then find items to buy and cook up.
  • Eat the rainbow! Find an item of produce in each color to sample and buy.

📍Wisconsin State Capitol Square; Saturdays from 6:15 AM—1:45 PM; April—November

🔗 More details are here!

Do the Thrift Store Challenge

Madison’s got some great second hand stores, and it’s always fun to explore what they have to offer. Want to inject some playfulness into your next thrifting expedition? Try out the thrift store challenge! Here are some potential rules:

  • Set a budget (say, $5, $10 or $20) for each person to work with.
  • Then, pick an amount of time (5 or 10 minutes). Each person sets a timer on their phone and dashes off to search for a ridiculous outfit for the other participant. Remember to stay within budget!
  • When the timer is up, try on the outfits and have your classic fashion montage moment. Strike a pose and snap a photo!
  • If you dare, buy and wear the outfit that your partner selected for you on your next outing.
  • Repeat as many times as you’d like, and pick different parameters to mix it up. For example, maybe you want to work with a theme like high school archetypes, space cowboys, or Old Hollywood, or select only red items or items that begin with certain letters of the alphabet.

📍St. Vincent de Paul’s Willy Street Location—1309 Williamson Street; St. Vincent de Paul’s Dig & Save Outlet (pay by the pound!)—1900 South Park Street; State Street Ragstock—329 State Street

🔗 There are so many good options for thrift stores in the area. Here’s a Reddit thread with lots of recommendations.

Float Down the Sugar River

Stock up on snacks, grab your hat and sunscreen, and head on over to the Sugar River for a chill couple of hours of floating. S & B Tubing in Albany (about 30-40 minutes outside of Madison) rents inner tubes and coolers and provides a shuttle back to where you start your float. All you have to do is show up!

Inner tubes are $20 per person and glass and styrofoam aren’t allowed on the river.

📍100 E Main St, Albany

🔗 Visit S & B Tubing’s website.

Go to Comedy on State

We always leave Comedy on State feeling much better than when we came in! This iconic basement standup space attracts some of the best comedians in the country, including SNL alumni, Daily Show comics, and more.

Get a quick bite to eat at Teddywedger’s or Ian’s before or after the show and take a relaxed stroll down State Street to digest.

Note that all shows are 18+ and that there is a two-drink minimum per person. The menu menu includes both non-alcoholic and alcoholic beverages.

📍202 State Street

🔗 See all upcoming events at Comedy on State.

Go Disc Golfing

One of Alex’s high school hobbies was disc golfing with his pal Steiny. (He even scrawled names for his discs on them with a Sharpie! “Beepie” is pictured in the photo to the left.) Recently we decided to lean into the high school nostalgia and toss around some discs, and it was a great evening.

If you don’t have your own discs, The Madison Public Library system has some that you can check out. Read more about that here.

There are a handful of nice courses—most of them with 18 holes—to choose from. Before hitting your chosen course, you’ll need to pay a fee of $7 per person at the course entrance or online.

📍 See a list of courses in the area here. We like going to Capital Springs!

🔗 Learn more about disc golfing in Madison.

Go to Olbrich Botanical Gardens

Another must-visit Madison spot, Olbrich is an especially wonderful spot to visit in the winter when you’re dreaming of far-flung tropical locales. The Bolz Conservatory is a balmy glass pyramid stocked with vibrant orchids, birds with showy plumage, and calming waterfalls. In the warmer months, the outdoor gardens boast a variety of plants. Be sure to visit the Royal Thai Pavilion, the only one of its kind in the continental U.S.

Entry to the indoor gardens is $6 per adult. The outdoor gardens are free to wander.

📍3330 Atwood Avenue

🔗 Read all about Olbrich Botanical Gardens.

Paddle Lake Monona

Head on over to Brittingham Boats to pick out a kayak, canoe, SUP, or paddleboard, then hit the lake! We like to paddle by Monona Terrace for a fantastic view of the Capital. If you’re feeling ambitious and have a bit of time, you can do an out-and-back down the Yahara River or Starkweather Creek (which is a nice segue to our next activity idea!)

📍701 West Brittingham Place

🔗 See Brittingham Boats’ hours and rent your watercraft of choice online!

Paddle to Olbrich Beer Garden

This is the perfect activity for a summer or early fall evening! Enjoy a late afternoon paddle and watch the sunset over the lake, drink or pretzel in hand. Remember to bring an ID to get into the beer garden, even if you won’t be imbibing.

📍Park at Olbrich (3527 Atwood Ave.) and rent watercraft there. Alternatively, if you have your own watercraft, you can put your boat(s) in at 801 N. Oak St. to paddle down Starkweather Creek toward Lake Monona and pull out your boats on the beach alongside Olbrich Beer Garden!

🔗 See the Olbrich Beer Garden menu and read more.

➡️ Read our full guide to paddling Starkweather Creek.

Sauna and Cold Plunge

Nothing gets the endorphins going like a sauna and cold plunge! Tuli, pictured above, is Laura’s personal favorite. Located on the Sugar River, it’s a traditional Finnish sauna with a wood stove; book a private session or snag a community sauna spot for a better deal.

Bergamot’s traditional dry sauna is another great option. Book a spacious sauna suite for access to a cold shower and add more guests for an additional fee.

We have yet to visit Saunaday but have heard glowing reviews of the infrared sauna, Hinoki Hot Soak, and social environment there.

📍Tuli—6858 Paoli Road, Belleville, WI (in front of Seven-Acre Dairy); Bergamot—83-2 Globe Drive #102, Madison; Saunaday—315 South Blount Street, Madison

🔗 Learn about Finnish sauna etiquette and ogle the amazing World Sauna Award winners.

Visit Sassy Cow Creamery

Lean into Wisconsin life and take a tour at a family-owned organic farm. You’ll be able to see how milk is bottled and buy fresh ice cream, and if it’s summertime, you can also meet a cute calf. Sassy Cow is about a 20-minute scenic drive from Madison.

📍W4192 Bristol Road, Columbus

🔗 Schedule your tour here!

$$

Attend a Pottery Class at Dongzhu Pottery Studio

Think you’d like to give wheel throwing a spin? Learn how it works and get your hands dirty in a fun environment with a one-night class at Dongzhu Pottery Studio.

Try-It Wheel classes are held Fridays and Saturdays from 6-7 PM and cost $30 per person. All materials are provided.

📍 Dongzhu has several locations, but pottery nights are held at 1925 Monroe Street Suite 100 in Madison and 661 University Avenue in Middleton.

🔗 See Dongzhu’s offerings.

Catch a Performance at American Players Theater

Even if you’re not a big Shakespeare fan, you’re going to want to see a show at the Tony-winning American Players Theater (APT) in Spring Green. It’s a whole experience. The acting is stellar and immersive; even the bats swooping over the stage haven’t taken us out of the vibrant world created on the outdoor stage.

Pack a picnic dinner to eat at a table on the beautiful property. When the horns blow, you’ll want to start walking up the hill toward the theater. We recommend wearing long pants and bringing a sweatshirt. It can get buggy and chilly at night. We also recommend buying gummy bears at intermission. IYKYK.

📍5950 Golf Course Rd, Spring Green

🔗 See the APT schedule here.

Enjoy a $100 Burger (and Scenic Flight)

Have you heard of the $100 burger at the Jet Room? Sure, it’s a solid meal, but what you’re really paying for is a thrilling 30-minute scenic flight over Madison. This is a bit of a splurge but a very fun, worthwhile thing to do on a special occasion. It was enough to give us both dreams of becoming a pilot! (Maybe in another life…)

You can either speak with a representative from Wisconsin Aviation in person or call 608-268-5000 to book a time for a flight. Then, purchase a certificate at the Jet Room in the Wisconsin Aviation terminal building during normal business hours.

📍3606 Corben Court, Madison

🔗 Learn more about the Jet Room and drool over the menu (the cinnamon rolls are highly recommended.)

Take a Cooking Class at Orange Tree Imports

Located in the heart of the Monroe Street Business District, Orange Tree Imports is a speciality store that has been around for over 50 years! Local chefs hold cooking classes on the second floor, a fun opportunity to add some more recipes to your kitchen repertoire.

We went to a Nepali cooking class at Orange Tree and still recreate the evening’s menu from time to time.

📍1721 Monroe Street

🔗 Check out the cooking class schedule here.

Bonus Resources

Here are some handy links that we refer to a lot when we want to know what’s going on during a particular week. This list is by no means exhaustive but should help you get started on your brainstorming.

Events Calendars

  • Isthmus— Brought to you by a beloved independent, local news source, this is probably one of the most exhaustive events calendars in town.
  • CityCast Madison— This is also a solid compilation of events, many of which are music and entertainment-related.
  • Destination Madison— Recurring and one-time events compiled by Madison’s tourism promotion org.

Performance Venues

  • The Orpheum— An ornate 1920s theater on State Street that hosts comedians, speakers, and musicians.
  • The Majestic— Just a block away from Capitol Square on the opposite side of the Orpheum, this large, historic theater hosts some big names in music.
  • The Barrymore— This near east side venue hosts everything from film festivals to book talks to sit-down concerts.
  • The Sylvee— Great spot to see indie bands and emerging artists, plus some more established groups.
  • The High Noon Saloon— This smaller venue offers a full calendar of rock, punk, and grunge acts—and check out Nerd Nite and the Moth, too.
  • Breese Stevens Field— Home to Forward Madison, the stadium turns into a festival and concert space throughout the warmer months of the year.

Local Sports Teams


Anything to add? Let us know in the comments!

One response to “26 Creative Date Ideas in & Around Madison, Wisconsin”

  1. […] Do you have any other favorite Madison events? Let us know in the comments, and check out even more fun activity ideas in this post here! […]

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