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City Cast Madison

Ava Wojnowski

Do you know what “cuffing season” is? As the weather gets colder and the holidays approach, some singles tend to be on the lookout for a new relationship – at least to last through Valentine’s Day, anyway.

On the City Cast Madison podcast today, host Bianca Martin and executive producer Hayley Sperling hit the streets with their microphones to find out about the state of the Madison dating scene.

Not sure how to get that first date rolling? We’ve also curated a list of 50 date ideas in and around Madison for you to take advantage of now and when the warm weather rolls back around.

Rent a canoe, paddleboard, kayak, or more with 

Tackle trivia night at one of the many bars in Madison. My go-to is the trivia at 

Give our podcast with the mastermind of trivia, Paul Guse, a listen!

 is all the rage… why not try it on a date?!

 is free for entry and you can even grab a bite nearby at 

Go on a sunset cruise on Lake Mendota with 

 whether it is football, hockey, volleyball, or something else!

For something more adventurous, try mountain biking at 

Learn a skilltogether like crocheting or pottery at 

 in Cambridge offers wood-fire pizza nights and live music, a perfect date combination.

Enjoy a filling breakfast at the Madison classic, 

Catch the sunset over the city with a couple of cocktails at 

 makes for a great date spot whether it be for a coffee or a cocktail.

for some dueling pianos and great drinks.

 is a great place to practice your golf swing on a date.

. They also have their “cheap date night” on Tuesdays.

When it gets colder, lace up your skates at the 

Drive outside of the city and go for a hike at 

Grab a pitcher of beer and a brat on the terrace at 

What’s Your Go-To Date in Madison?

We’ve also curated a list of 50 date ideas in and around Madison for you to take advantage of now and when winter rolls around.

The Best 50 First Dates in Madison

Find the best of everything that Madison has to offer.

Madison’s Best

Madison's Best

Do you remember?! It’s officially September! You know what that means — football, festivals, and a whole lotta fun. This September Guide breaks down various activities for folks to enjoy in Madison.

U! Rah! Rah! It’s football season at UW-Madison. From Jump Around to Build Me Up Buttercup, there are a ton of traditions that one can take part in this fall.

There are a ton of places to catch a tailgate along Regent Street in Madison. Popular bars include 

. These are all close to the stadium, making it an easy commute if you have tickets.

Parking can be a struggle for all football fans. A ton of houses around the Camp Randall area are often selling parking spots for folks. There is also parking at the Union South event parking lot for people to use. Lastly, there are also 

 and a shuttle to help bring people to the stadium.

 will be held on Sept. 21, taking over most of Monroe Street. This free event will have music, a variety of activities, and vendors from local businesses. A great way to spend the day with the family!

will be taking place on Sept. 21-22. There will be a ton of music performances, including a kid’s stage. There will also be a ton of vendors and food for folks to enjoy while the music plays. And don’t forget about the parade that will be taking place at 11 a.m. on Sunday.

Head on over to New Glarus for their annual 

. With a ton of beer, brats, and lederhosen, this festival will make you think you’ve been transported to Germany. This event has free admission and will take place from Sept. 26-29.

Calling all vegans! Madison is having their 

 at Lunney Lake Farm Park. This event will take place on Sept. 28 from 11 a.m. to 5 p.m. There will be a ton of local restaurants and dessert options for folks to sample and enjoy.

What’s On Your September Bucket List? 

Do you remember?! It’s officially September! You know what that means — football, festivals, and a whole lotta fun. This September Guide breaks down various activities for folks to enjoy in Madison. 

Your Guide to Madison in September 2024

One of the longest-running outdoor festivals is returning to Madison this weekend, as the 

Orton Park Festival is celebrating its 59th year

! From Aug. 23 to 25, Madisonians can dance to live music, get food from local food vendors, participate in “quirky traditions,” and much more.

Heading to this weekend’s festivities? Here’s a short and sweet guide 🎉

one of Madison’s most iconic neighborhoods, Marquette.

 The Orton Park Festival is just one of the many free music festivals the 

 puts on. It also serves as a fundraiser for the group.

The three-day festival weekend kicks off with Family Night at 5:30 p.m. There will be multiple food vendors, wine, craft beer, and ice cream to enjoy while watching a performance of the Forward! Marching Band.

The day begins at 11:45 a.m. with Broken Boards, followed by a day’s worth of musical performances. The day’s final show is from 

On the final day, head to the traditional jazz brunch at 9 a.m., featuring the Madison East High School Jazz Combo. Musical performances begin again at 11:45 a.m. with Frisson and conclude with the headlining performance starting at 6:15 p.m.

Singer, rapper, and writer Dessa will be taking the stage on Sunday. 

City Cast Madison spoke with the Midwestern royalty ahead of her performance

 to ask about her roots in the Midwest, her past experiences performing in Madison, and her latest projects.

overview of all of this year’s performances

Orton Park Festival’s Facebook for updates

🎧 What To Expect From Dessa’s Set

One of the country's longest-running outdoor festivals is returning to Madison on Aug. 23 through to Aug. 25. Here's a guide to when Madisonians can dance to live music, get food from local food vendors, participate in “quirky traditions,” and much more. 


A Guide to the Orton Park Festival in Madison

The Orton Park Festival in Marquette

Everything to know about Madison neighborhoods: Where to go, eat, shop, drink, and more.

Madison Neighborhood Guides

Neighborhood Guides

Madison is full of places to nestle up with a good book. With coffee shops and fun bars, there are plenty of options. But what if you don’t want to spend money on a drink? Here’s a list of 14, free places to sit down with a good book.

 are a great place to set up and read a good book. There are nine different libraries to choose from, offering something for everyone.

 is also a popular spot for readers. There are spots for kids to enjoy some reading time and for adults to enjoy peace and quiet.

is a great spot to sit and read. Surrounded by art and big windows, how could you not enjoy this secret reading spot? There aren’t many spots, so go early if you want to snag space.

 is a cool spot in Madison to enjoy your book. With a ton of natural light, it is a great place to feel like you are outside while staying inside. Not to mention the real TREE that is inside!

Wisconsin Historical Society Reading Room

 is a popular spot for many Madisonians. This quiet location will make you feel like you’ve traveled to the world of Harry Potter. With marble columns and long wooden tables, it really feels like you left the real world behind.

. This is one of my favorite places to read a book. It’s quiet with plenty of seats, including some Adirondack chairs.

 has a ton of seats throughout its grounds. This is a great spot for an outdoor, quiet read.

Madison is stuffed to the brim with parks. Some popular ones to crack open your novel include 

 if you find some good trees to set up a hammock!

While it may be deemed basic, how could the 

 not be included? With a beautiful view of Lake Mendota, this is the perfect place to read your book throughout the end of summer. And during the colder months, head inside to the Lakeview Lounge for spectacular views and plenty of seats for reading.

 is one of my favorite places to read, thanks to its diverse seating options. Whether I’m in the mood for a cozy nook or a more open space, I can always get lost in my book.

 has both good indoor and outdoor seating options. They even have a basement with couches for a cozy spot to enjoy your book on a rainy day.

 is a great place to get a book while sipping on a coffee drink, cocktail, beer, and more. There is also a bookstore in this café, so if you don’t have a book you can grab a new one and enjoy!

is a great spot on a cool summer day to enjoy your current read. However, if it is hot, they have a mist machine to keep everyone cool.

Where Do You Read? 📚

The Best Free Places To Read in Madison

As students begin to make their return to campus and summer winds down, there are still a ton of events to celebrate August in Madison. Wondering where to begin? 

The Mustard Museum will host the annual celebration of 

 in downtown Middleton. With a ton of different vendors and live music, National Mustard Day is turning the town yellow! 

 will occur Aug. 2-3 at W.G. Lunney Lake Farm County Park. Three different stages show off various types of music, dances, workshops, and more.

 will take over the Capitol Square Aug. 31 and Sept. 1. There will be more than 80 different food vendors from all around the Madison area for folks to try out and enjoy. There will also be a bunch of different musical artists.

 which will take place Aug. 11. The community takes advantage of blocked off streets, allowing them to bike openly on the roads to different Madison parks.

Many leases on and around the isthmus start in mid-August, which means 

is here! This unofficial local tradition is a time when residents put out their unwanted household items for other Madisonians to scoop up. This is a hectic time for Madison, so make sure to 

 in Camp Randall to kick off the 2024 season. (Literally.) The Badgers will play Western Michigan at 8 p.m. U Rah Rah!

While Madison is still warm, take advantage and 

. This beautiful trail takes you along rolling hillsides and tree-covered canopies. You can get onto this trail from the Southwest Commuter Bike Path.

 to kick off the return to school! Or, just soak in the final days of summer in Madison. Grab a paddleboard or a kayak and head out on Lake Mendota.

 game to cap off the perfect Madison summer. The Madison Mallards will have home games on Aug. 2, 4, 5, 8, and 9. The Night Mares will have home games on Aug. 1, 3, and 6.

 at Breese Stevens Field on Aug. 14 at 7 p.m. They will be playing the Charlotte Independence. Can’t make that game? No worries! There’s also one on Aug. 29 at 7 p.m. against Union Omaha.

The August Agenda 😎

As students begin to make their return to campus and summer winds down, there are still a ton of events to celebrate August in Madison. Wondering where to begin? You’ve come to the right place.

Your Guide to Madison in August 2024

, and if anyone knows how to put on a fair, it’s the people of Wisconsin! This summer staple offers rides, classic fair foods, live music, horse shows, and a whole lot more. Taking place at the Alliant Energy Center from July 18-21, there is plenty of opportunity to get in on all of the action.

Classic Fair food is always a crowd pleaser and the Dane County Fair never disappoints. Personally, I am most excited for a Bahn Mi sandwich from 

, a dipped frozen cheesecake on a stick (I mean come on!) at 

The Dane County Fair always offers a variety of activities, guaranteeing something for everyone. Be sure not to miss checking out 

 on July 18 at 6 p.m. If that isn’t your speed, head to the 

 at 5 p.m. on July 19. Another event that caught my eye is the 

… ouch! That will be at 5 p.m. on July 21. You can see the full event schedule 

The gates are open from 8 a.m. to 8 p.m. every day of the fair. Events will go on as late as 11 p.m., but you can’t get into the grounds after 8 p.m. Parking is free! You can park after the main gate on Rimrock Road or in the South lot off of Rusk Avenue at the Rusk gate. Make sure to hydrate and enjoy the fair 😁

This summer staple offers rides, classic fair foods, live music, horse shows, and a whole lot more. Taking place at the Alliant Energy Center from July 18-21, there is plenty of opportunity to get in on all of the action.

Your Guide To the Dane County Fair

We asked for y’all to give us suggestions of must-adds to our Madison bucket list. Here are some ideas that your fellow Madisonians came up with 🌞

Set sail on Lake Mendota and learn to sail with the Hoofers Sailing Club. The club is open to all levels, so if you are just beginning and want to try it out, they have lessons for you.

This festival will take place at McPike Park from July 11-14. With artists from all around the world, this is a rare opportunity to see a bunch of different performances in one place.

This event will take place in the North Star neighborhood (formally the McClellan Park neighborhood) Aug. 3 from 11 a.m. to 8 p.m. With live music, food trucks, and family fun, there is much to do at this festival.

 local markets across town selling farm-fresh produce, cheeses, meats, and more!

With the best view in the city, the Terrace at Memorial Union is a great spot to grab a bite during the day. They also offer a variety of 

 on the terrace, great to enjoy with friends and family.

Wingra is a great place to rent different paddling and boating equipment. They also offer different fun 

 like full moon paddles or paddling out to an ice cream boat.

 From July 12-14, there will be a variety of bouncy structures set up at Angell Park in Sun Prairie. One ticket gets you three hours and you sign up for the session that best suits your child. Looking for more kid-focused activities? 

 From July to August, the sunflowers at Eugsters’ Farm are in bloom. There are about 500,000 sunflowers to see across 15-acres — what a cool sight to see!

 Head on over to Brittingham Park to enjoy their courts in a friendly match of Tennis. Or maybe you would prefer pickle-ball? They also have courts for that!

We asked for y’all to give us suggestions of must-adds to our Madison bucket list. Here are some ideas that your fellow Madisonians came up with. 

Madison's Summer Bucket List 

July is just around the corner and Madison is the place to be. But where to begin? We’ve curated a list of different ways to spend the month and dug into more events in the City Cast Madison podcast.

 from July 11-14. This is a free festival with a ton of artists from all over the world.

. Taking place on State Street and the Capitol Square, there will be many local shops and restaurants offering different discounts, larger patio spaces, and live music.

 of where to catch live music around town.

 is a great way to spend a summer afternoon. Brittingham Boats will hold this event July 5,12,19, and 26. Get your appetite ready for burgers from the floating burger pontoon in the middle of Monona Bay.

 is a two-level pontoon boat that can hold you and up to 29 of your friends. Bring your own food and drinks and enjoy the grill that’s onboard.

 will be at the Black Hawk Country Club. These will take place July 4 at dusk. They will also host a parade, picnics, and more.

 will take place between July 3-4 at Winnequah Park. The fireworks will be on July 4 at dusk. There are also scheduled events throughout both of the days to celebrate the holiday. This is (

) the fest’s last year, so don’t miss out!

 will have a fireworks display after their game July 3 against the Wisconsin Rapid Rafters. What’s a better summer activity than a softball game and some fireworks?!

 and cruise on Lake Mendota to get the best seat for the fireworks. Book a pontoon now from 8-10 p.m. on July 4.

July is just around the corner and Madison is the place to be. But where to begin? We’ve curated a list of different ways to spend the month and dug into more events in the City Cast Madison podcast. 

Oh My! It's Already July!

Oh My! It’s Already July!

If you're like me, you’ll do anything to get into a body of water during the summer months. Madison is a great place to go swimming with the many lakes the city has to offer. But there are a few things to keep in mind before diving in.

The City of Madison constantly checks the safety of the water in our lakes. For updated information on each beach, you can check with 

 to see what beaches and lakes are open for swimming. While the city tries to be as accurate as possible, conditions can change quickly. This means you should still keep an eye out for green-blue algae.

Now, you may wonder what exactly you’re looking for when it comes to 

. The city describes it as “algae that looks blue-green, green, reddish-purple, or brown, murky looking water that has a texture similar to ‘pea soup,’ a layer of scum or puffy blobs floating on the surface, and a strong musty odor near the water.”

Coming into contact with blue-green algae can cause skin irritation, nausea, respiratory problems and more. The importance of being smart is key when it comes to swimming in these lakes!

If you do come into contact with the blue-green algae, make sure to 

Dogs are more affected by the blue-green algae because they're smaller than humans. Make sure to keep an eye on where your dog swims and if they ingest any water. Also, make sure to wash off your dog after they swim in a body of water that may have the blue-green algae.

Ready for a swim?

Madison is a great place to go swimming with the many lakes the city has to offer. But there are a few things to keep in mind before diving in. Here is your guide on how to safely swim in Madison this summer. 

Is It Safe To Swim?

Get to know the natural side of Madison: the plants, animals, weather and more that make our city unique.

Madison Urban Almanac

Urban Almanac

In classic Wisconsin fashion, we have gone from cold spring mornings right to sweltering humidity. I curated a list of places for you folks to cool off and take a break from the balmy weather. These are some of my favorite ways to beat the heat in Madison.

For the ultimate break from the heat, take a dip in the Goodman Pool. A great place for the whole family to take a break from the heat.

From kayaks to the eight-person stand-up paddleboard, there are plenty of rentals one can get from Outdoor UW. Set sail on Lake Mendota for the perfect way to avoid the heat!

With huge windows, this spot allows for natural light with the luxury of air conditioning. Enjoy a margarita, or my personal favorite, their yerba juice.

Classics are classic for a reason — grab a pitcher at the terrace while enjoying the views of Lake Mendota.

What is a better way to cool off than a cold beer? Olbrich Biergarten is on Madison’s lake loop, and is a great spot where you can get a beer and play cards with your friends.

Bike or drive to this wonderful ice cream spot located on Lake Monona. Featuring Babcock Hall Ice Cream, there are plenty of flavors to choose from and enjoy on their patio.

Located on King Street, this ice cream shop has a variety of quirky flavors that are sure to not only cool you off, but also satisfy your sweet tooth. My go to is fig & honey!

things to do

The Best 50 First Dates in Madison

Your Guide to Madison in September 2024

The Orton Park Festival in Marquette

Latest articles

The Best 50 First Dates in Madison

Your Guide to Madison in September 2024

The Orton Park Festival in Marquette

The Best Free Places To Read in Madison

Your Guide to Madison in August 2024

Your Guide To the Dane County Fair

Madison's Summer Bucket List

Latest articles

The Best Free Places To Read in Madison

Your Guide to Madison in August 2024

Your Guide To the Dane County Fair

Madison's Summer Bucket List

Oh My! It’s Already July!

Is It Safe To Swim?

The Best Ways to Beat The Heat