
City Cast Madison
💗 50+ date ideas for Madisonians
August 27, 2024
Heyyyyyy, Madison! I am happy to say I am back for the next couple of weeks to write this newsletter for you folks ✍️ Today’s newsletter is (almost) all about dating. We tried to curate the best date ideas for partners, friends, or even a solo date!

What's CITY Talking About?
📝 Madison’s New BizReady Program
- Applications are now open for the city’s BizReady Program. This opportunity provides local business owners in Madison with training, mentoring, and networking opportunities for their businesses.
- This is a free resource with $300,000 in funding provided by the American Rescue Plans fund. [City of Madison]
🎉 Grand Opening of Black Business Hub
- The Black Business Hub opened Saturday with a ribbon-cutting ceremony. This new space will offer accessibility to the 40 Black-owned businesses in Madison while also helping new businesses open.
- Many local politicians and business owners spoke at the ribbon-cutting event. This hub is located at the Village on Park Street. [15 WMTV]
🌯 Todofresco Scales Back
- This restaurant, which opened last September, has closed its counter-service operations. The Latin-influenced restaurant is moving to catering only.
- They serve a variety of items including warm bowls, salads, breakfast burritos, and pressed juice.
- Related: Want to learn more about the changing restaurant scene in Madison? Give our podcast a listen! [🔒WSJ, City Cast Madison 🎧]


The Best 50 First Dates

The City Cast Madison team gives you suggestions for your next date night. Whether it’s with your partner, friends, or just yourself, there is a ton to do with a variety of budget options. Give it a listen!

Activity Oriented Adventures
Take a walk through the Chazen Art Museum, which is free to enjoy.
Tackle trivia night at one of the many bars in Madison. My go-to is the trivia at The Harmony Bar & Grill. Give our podcast with the mastermind of trivia, Paul Guse, a listen!
Set up a hammock at any of the many parks in Madison.
Stargaze on Observatory Hill, overlooking Lake Mendota.
Play cards at the rooftop bar Camp Trippalindee.
Foodie Dates
Grab a bagel sandwich from Gotham Bagels and sit by the capitol building.
Pick up a sweet treat from Bloom Bake Shop on Monroe Street.
On Tuesdays, Merchant offers a date night deal on their menu.
Let’s Grab Drinks
Get a couple of glasses of wine at the Wollersheim Winery & Distillery.
Get an Old Fashioned at The Old Fashioned!
Catch some music at Lola’s Hi/Lo Lounge. They also have their “cheap date night” on Tuesdays.
Get your board games out at Garth’s Brew Bar with a cold beer in hand.
Seasonal Ideas
When it gets colder, lace up your skates at the Edgewater Ice Rink.
Drive outside of the city and go for a hike at Devil’s Lake.
Schuster’s Farm is the perfect fall date with a corn maze, apple cider, and more!

Take Me Home Tuesday

Say hello to Roger! He has two true loves – food and people. He enjoys receiving attention, including pets, playing with his toys, and engaging in friendly chats. Roger is food-motivated, and while he’s sure to steal your heart, he’ll also try to steal your lunch. Roger is a member of DCHS’s Lonely Hearts Club, and his adoption fee has been reduced to $10.

What To Do
Tuesday, Aug. 27
- Bigtooth at The Harmony Bar and Grill
- Board Games and Beer at Starkweather Brewing Company
- Latin Dance Night - Bachata Class & Dance Social at Cafe CODA
- LIVE MUSIC: Former Critics & Clementine at The Rigby
- Lucid Tuesday at Crucible
- Lunch Time Live at King Street Walkway - Wisconsin Capitol Square
- Madison Django Jazz Jam at Leopold's Books Bar Caffe
- MAMAs Blues Music Community Listening Event and Jam Session at Red Rooster Madison
- Open Mic at The Bur Oak
- Poetry on Tap at Minocqua Brewing Company
- Rudens (The Rope) by Plautus at Arts + Literature Laboratory
- Trivia Night at The Rigby
Thanks for reading today’s newsletter. We’ll see ya tomorrow! 😄
— Ava Wojnowski
Free · Daily
