Plus, longer days + the Italian Street Festival.
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🏡 Stay in a little piece of history

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At the Airbnb, you’ll find two murals created by local artists to celebrate David Letterman — this one is by Amiah Mims. | Photo by Chris Bucher Photographs
With the Indy 500 and the Pacers’ Game 3 of the Eastern Conference Finals happening on the same day over Memorial Day weekend, we’re not surprised to hear that hotels were sold out across the state + Airbnbs were thriving.

Bookmark this story because we’re sharing an Airbnb that you may want to consider for your next staycation — or if you’re just a big David Letterman fan.

For decades, it’s hidden in plain sight, but now you can stay in the Indiana-born and late-night TV icon’s childhood home in Broad Ripple.
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Owner Krystin Wiggs wanted to recreate the feeling of the Ed Sullivan Theater, where Letterman filmed his famous late-night show.

Photo by Chris Bucher Photographs

Inside the home, you’ll find it decorated with memorabilia, including pictures of celebrities appearing on “The Late Show.”

The charming three-bedroom, two-bath bungalow can accommodate up to six guests. It’s available for $200 per night on Airbnb, with a two-night minimum. Pets are welcome.

Asked

Which of these fun facts about David Letterman’s connection to Indy is FALSE?

A. Letterman was born in Indianapolis + graduated from Ball State in 1969.
B. He took a position as a weatherman on local Indianapolis television station WTHR.
C. He is a part-owner of Rahal Letterman Lanigan Racing, a team with two Indy 500 victories.
D. He went to Broad Ripple High School.
Take a guess
Dance Kaleidoscope

Events

Tuesday, May 27

Build Your Technology and Computer Skills | 11 a.m.-1 p.m. | Central Library | Free | Take a skills assessment to develop a custom learning plan for 10+ tech topics.

Wednesday, May 28

Yoga at the Market | 10-11 a.m. | City Market | Pay what you can | Join a refreshing mid-morning flow right in the heart of downtown.

Thursday, May 29

Indianapolis Indians vs. Nashville Sounds | 6:35 p.m. | Victory Field | $13+ | It’s Thirsty Thursday and Bark in the Park night — bring your furry friend and get discounted drinks.

Friday, May 30

Candlelight: Best of Hip-Hop on Strings | 8:45-10 p.m. | The Cyrus Place | $54 | Discover reinvented hip-hop favorites under the gentle glow of candlelight.

Saturday, May 31

A Spring Bake Sale | 10 a.m.-12 p.m. | 4 Birds Bakery | Cost of purchase | Support local bakers + enjoy treats from 4 Birds Bakery, Borage, Vegan by Emma, The Power of Pastry, Indy Dough, and Ginger Snapped.

Sunday, June 1

Plant Stop, Won’t Stop | 12-5 p.m. | Broad Ripple | Cost of purchase | Shop 90+ vendors selling plants and plant-related goods, plus enjoy a pet-adoption pop-up, music, food, and drinks.

Saturday, June 14

Rock the Ruins | Saturday, June 14-Saturday, Aug. 16 | Locations vary | Rock the Ruins returns to Holliday Park with a can’t-miss lineup this season — and for the first time ever, it’s expanding to Broad Ripple Park, bringing even more live music to the heart of the city.*
Make the most of May
Click here to have your event featured.

Finance

Be an early-stage investor in this proven founder’s new venture

Presented by Pacaso
Pacaso-updated-article-may-2025
Pacaso’s platform offers easy purchase, ownership, and enjoyment of luxury vacation homes. | Photo by Pacaso
The wealthiest companies target the biggest markets — like Nvidia, skyrocketing ~200% higher in 2024 on the $214 billion AI market’s tailwind. That’s why investors like Pacaso.

Created by the founder behind a $120 million exit, Pacaso’s platform offers easy purchase, ownership, and enjoyment of luxury vacation homes. And their target market is worth $1.3 trillion.

No wonder Pacaso earned $110 million+ in gross profits already. And you can join notable investors like Maveron as a Pacaso shareholder for just $2.90/share.‡‡
Invest

News Notes

Today Is

Memorial Day, a federal holiday, meaning civic offices, most state offices, banks, and public libraries will be closed. Observe the day at the Indiana War Memorial and Soldiers and Sailors Monument.

Weather

9 p.m. sunsets have arrived. We’re gaining about one minute of daylight per day — leading to the summer solstice (aka the official start of summer) and the longest day of the year, which will land on Friday, June 20 when the sun sets at 10:41 p.m. (WTHR)

Development

The Indianapolis Motor Speedway announced plans to spend $18 million to build a restoration + event facility just 2.5 miles from the track. It will begin construction of the 60,000-sqft facility later this year and is expected to be complete by the end of 2026. (IBJ)
Hotel Carmichael has been nominated for a Conde Nast Travelers Reader’ Choice Award. You can vote for the Carmel Autograph Collection hotel through Monday, June 30.

Plan Ahead

Mark your calendar. The beloved Italian Street Festival is returning to Holy Rosary Catholic Church for its 40th year on Friday, June 13 + Saturday, June 14, with 25+ food vendors serving up Italian meats, pastas, salads, and desserts. The free, family-friendly event will also feature live entertainment.

Mansion Monday

Saddle up. You could live out your equestrian lifestyle dreams with this 5-bedroom, 3.5-bathroom full-brick home that sits on more than five acres in Zionsville. See the property, which features a two-stall barn tailored to horse care and enjoyment.

Sports

We’re still not over it. The Pacers did it again, erasing a 17-point fourth quarter deficit and pulling off another miracle. But what happened in Games 2 + 3? Locked On host Tony East breaks it all down.

Home

Picture this: You’re whipping up a delicious spread in your newly renovated kitchen — yum. The transformation from drab and outdated to new and modern was easier than you thought with help from the product experts and design consultants at Kohler. See how they can turn your vision board into reality. Get some inspo here.*

Travel

Hit the road to Milwaukee for a one-of-a-kind Memorial Day Weekend getaway at the Harley-Davidson Museum. With 20+ acres of fun in downtown Milwaukee, it’s the ultimate moto experience (think: 120+ years of legendary motorcycle history to explore). Plan your visit.*

Biz

Skip the calls — with our self-service ad portal, you’re just a few clicks away from showing off to the whole city. Advertising made so easy, it’s practically your new side hustle.

Shop

Run, don’t walkAthleta’s Memorial Day Sale is ending tonight. Save up to 60% off sale items + 40% off breezy tanks, go-to dresses, and warm-weather staples.*

Finance

$2.80 per share is almost gone. Top firms like SoftBank have already invested in Pacaso, the startup disrupting a $1.3 trillion real estate market. Now, after 41% YoY gross profit growth, they recently reserved the Nasdaq ticker $PCSO. Until Thursday, you can invest for just $2.80/share.‡‡*

Jobs of the Week

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The Buy

A great deal from Amazon’s Memorial Day sale. Note: Prices subject to change.

⭐ Get 38% off women’s Max Cushioning sneakers from Sketchers and feel like you’re walking on clouds (really, that’s what reviewers say).
⭐ Take 46% off a 10-piece wireless home security system — outdoor camera included.
⭐ Get 32% off a set of hypoallergenic 14K gold huggie earrings.
Shop all Memorial Day deals

The Wrap

I was shocked to find out about this Airbnb — and that one of my neighbors owns it. I met up with Krystin at the house + she showed me around and gave me a little backstory on how she found it. Follow our Instagram so you don’t miss that video interview coming soon. Looking for more unique stays around Indy? Check out our guide.

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‡This is a paid advertisement for Pacaso’s Regulation A offering. Please read the offering circular at invest.pacaso.com. Reserving a ticker symbol is not a guarantee that the company will go public. Listing on the NASDAQ is subject to approvals. Under Regulation A+, a company has the ability to change its share price by up to 20%, without requalifying the offering with the SEC.

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