Ashley Sill and I met where all good Des Moines friendships start – entry level jobs at the same insurance company.  Since meeting five years ago she has taken over our cute little city. 

Ashley now works at Principal Financial Group full-time and is a Read to Succeed program reader through United Way of Central Iowa. During the academic school year, she volunteers at Freedom for Youth as a Skills Class Instructor, teaching a variety of art classes to high school students. She’s also a WhizKids Program Leader, leading an afterschool program for K-5 kids in the Oakridge community. In case that’s not enough, she’s also a Sunday School teacher for HopeKids at Hope + Elim church. 

We knew that Ashley’s perfect Saturday in Des Moines would be compelling, so we asked her to write it down! If you’re new to the area, this is a must-read! 

As a Des Moines native, mastering the perfect summer Saturday in ~early adulthood~ has been a work of love, adventurous friends, and stumbling across amazing local finds. I absolutely adore this city and all it has to offer. 

If you want to go out in public, it’s almost guaranteed you’ll see someone you know. But if you want to be lowkey, there are 100 cool dives to duck out in and be a nobody. I love the ability to do both.

The Perfect Summer Day in Des Moines

My perfect Des Moines day always starts early and the weather is the key. A big ask in Iowa, I know! My favorite days are Saturdays in the late summer and early fall. Here’s what a typical Saturday in that time frame might look like:

My go-to line is that Des Moines is the smallest big city.– Ashley Sill

1. First things first, I’ve got to get moving. I start with a walk to Gray’s Lake!

Ashley Tip: Park on 11th street (outside of Cityville) and walk the trail to the lake and back. It is 3.3 miles round trip and way less busy than the Gray’s Lake lots on a nice day!

2. On the way home, I stop by the Downtown Farmers’ Market and grab pastries.

As we all know, there are so many amazing vendors and choices at the Downtown Farmers’ Market. If the market isn’t in season,  I’m either getting the almond croissants from La Mie or the sour cream, old fashioned donuts from Chu-Chu Donuts. Seriously amazing.

3. After I eat the pastries back at home, I get ready for the day and go shopping in Valley Junction or the East Village.

Depending on which neighborhood I visit, here are my go-to shops: 

East Village

Valley Junction

4. After afternoon shopping, I swing home and grab a picnic basket of snacks and/or lunch before heading to Jasper Winery.

There is nothing better than an afternoon on their grass with girlfriends. We all know their Thursday night summer concert series is amazing, but hitting an early weekend afternoon on the lawn is just as fun and still free.  Plus it’s more laid back and open! 

Ashley Tip: I like to mix in a couple local favorites to my charcuterie tray. These three are my go-to’s:

  • Oasis Hummus – I usually find it at the downtown HyVee
  • Maytag Blue Cheese – Find it at the Downtown Farmers’ Market or the downtown HyVee!
  • Mo’s Pretzels  – Think Dots, but better! I buy this at the Downtown Farmers’ Market or Gateway Market.

If the weather isn’t great, Cheese Bar on Ingersoll is my backup to Jasper Winery. Here’s the menu. I always try whatever Jefferson Cider Works cider they have on tap. My favorite is the hibiscus rose!

5. My evening preference is always something outdoors with live music!

There are so many options for outdoor live music in Des Moines at this time of year. My girlfriends and I frequent 300 Craft & Rooftop, Fleetwood at Saylorville (a floating bar on the lake!), Wooly’s, Lauridsen Ampitheater Concert Series at Water Works Park and more.

I could go on and on with other options, but the moral of this story is that with some sunshine and good friends, an amazing Saturday is always just around the corner in this special little place I call home. 😊

Ashley’s Other Favorites

We asked Ashley for some of her other favorite places to pop into in the Des Moines area. Here’s what she said:

Want more itineraries like this from cool people around DSM? Have a cool idea story?

Slide into our DMs.