By Dan Garcia Photographer Published Jun 25, 2023 at 10:26 AM

Festival City is hopping this summer! OnMilwaukee's Festival Guide is brought to you by Potawatomi Hotel & Casino. Escape the heat and step inside! 

A music icon graced the stage at Summerfest last night as James Taylor and his All-Star Band headlined the final night of Summerfest’s first weekend at the American Family Insurance Amphitheater. With some special support from notable Milwaukee Bucks superfan Sheryl Crow, Taylor delivered a memorable 19-song set complete with all of his biggest hits from his lengthy and accomplished career. 

Check our some of our favorite images from James Taylor and Sheryl Crow’s Saturday night performance at Summerfest to close out weekend one: 

1. Large print setlist 

James TaylorX

James Taylor’s hits are as big as his setlist on Saturday. He performed just 19 songs, but the setlist was literally big. Perhaps he forgot his readers back in Carolina. 

2. Soaking up the sun 

Sheryl CrowX

Fans were rewarded for showing up in time on Saturday night as Sheryl Crow performed a career-spanning set until sundown, warming up the crowd before James Taylor hit the stage. 

3. Hats off the to the headliner 

James TaylorX

With a Rock & Roll Hall of Famer and music legend like Taylor in the building, it was no surprise that fans filled the Amp to enjoy tracks like “Fire and Rain” and “Carolina In My Mind."

4. Bucks in six 

Sheryl CrowX

As many know, Sheryl Crow is a big Milwaukee Bucks fan, and before she even got through song four on her setlist, she took time to share her love for Milwaukee and give a little nod to her love of Giannis and company. 

5. Packed house 

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With names like Taylor and Crow on the marquee, it’s no surprise that fans filled up the Amphitheater to enjoy two of the biggest shows of the night. 

6. Having some fun 

Sheryl CrowX

If all you wanted to do was have some fun, then the Amp on Saturday night was the place to be this weekend. Sheryl Crow and James Taylor both proved at Summerfest why they are a couple of music icons and still got it!