Ann Arbor Area Events, Farmers Markets & Live Music: 5/29-6/4

May 29th–June 4th: Your weekly lineup of local news, events, and live music in Ann Arbor, Ypsi, Dexter, Chelsea & beyond!

Hi neighbors!


Wondering what to do this weekend? I've got you covered with local events, live music, and farmers markets popping up all over Washtenaw County. Whether you're in it for the funnel cake, fresh produce, or just looking for an excuse to leave the house and escape your laundry pile (no, just me?)—you’re in the right place.

🗓️ What’s Happening?

🎠 Milan Community Fair | Thursday–Saturday, May 29–31
Carnival rides. Funnel cakes. Small-town charm. If you’ve been craving a Ferris wheel and fried dough, Milan’s got your weekend plans covered.

🎶 Dexter Summer Music Series | Friday, May 30, 6:30–8:30 PM
Free live music at Monument Park (this week is Jean Wilson & Friends), surrounded by charming shops and friendly faces. BYO blanket or lawn chair!

🍽️ Taste of Ann Arbor | Sunday, June 1
A foodie’s dream: sample bites from your favorite A2 restaurants while enjoying live music (12–5PM at Main & Liberty). Pro tip: Wear loose clothing.

👟 Dexter–Ann Arbor Run | Sunday, June 1
A classic run along the Huron River with plenty of great views to soak up along the way.

🎤 Third Place [MusicFest] | Wednesday–Saturday, June 4–7
Ann Arbor turns into a stage during this 4-day music fest with a mission!

🥕 Farmers Markets This Week

Craving fresh produce, local honey, baked goods, or just a sunny morning stroll with a coffee in hand? Here’s where you can shop local and support our farmers this week:

🛍 Thursday, May 29
– Pittsfield Township Market | 2–6pm
– Manchester Market, Manchester Mill | 3–6pm

🌽 Friday, May 30
– Dixboro Market | 3–6pm

🍓 Saturday, May 31
– Ann Arbor Market (Kerrytown) | 7am–3pm
– Chelsea Market (Palmer Commons) | 8am–1pm
– Dexter Market | 8am–1pm
– Saline Market | 8am–12pm
– White Lotus Farms Market | 9am–2pm
– Ypsi Market – Depot Town | 9am–1pm

🧀 Sunday, June 1
– Whitmore Lake Market | 10am–2pm

🌱 Tuesday, June 3
– Dexter Midweek Market | 11am–3pm

🍅 Wednesday, June 4
– Ann Arbor Market (Kerrytown) | 7am–3pm
– White Lotus Farms Market | 9am–1pm
– Chelsea Midweek Market (State Bank Lot) | 10am–3pm

Grab your bags and enjoy the local goods! 🧺🌞

🏠 Thinking about making a move in the Ann Arbor area?  

Hi! I’m Bailey Walsh 👋 

Realtor, local expert, and lover of all things local. I live here, work here, and tend to know everything going on in the Ann Arbor area (hence, the newsletter).

Whether you're planning a move or just Zillow-scrolling at midnight with a glass of wine, I’m always happy to help.

Reach out anytime—whether you’ve got a real estate question or just need a solid coffee rec, I’ve got you.

🎵  Live Music Lineup

(Live music events in Ann Arbor/Ypsi unless otherwise noted & those marked with ($) charge a cover or require a ticket to the best of my knowledge)

Thursday, May 29th:
Keaton Royer and Josef Deas @ Weber’s from 6-9pm (no cover)
Lilly MacPhee @ Erratic Ale (Dexter) from 6:30-8:30pm (no cover)
Jake Reichbart @ The Earle from 7-9pm (no cover)
Eric Shore and Friends @ Ypsi Alehouse at 7pm (no cover)
Jean Wilson and Friends @ Zal Gaz Grotto from 7-9pm ($) 
Alina Morr & Urban Tropical @ Blue Llama Jazz Club from 7-8pm & 8:45-9:45pm ($)
Abigail Stauffer and The Wisdom: I Am Safe @ Kerrytown Concert House at 7:30 pm ($)
Flamy Grant @ The Ark at 8pm ($24)
Lester, Geranium Red, Spectral Threads, Nobody Wins @ The Blind Pig, doors at 8pm ($)
The Pherotones @ Last Word from 9pm-midnight (no cover)
The Gwenyth Hayes Trio @ The Ravens Club from 9pm-12am (no cover)

Friday, May 30th:
The Glen Leven Band @ North Star Lounge from 5:30-6:30pm (no cover)
Jim Salame (Dean Martin Tribute Artist and Impersonator) @ Lake Forest Golf Club at 5:30pm (no cover)
Scott Martin @ Mash (Ann Arbor) @ 6pm (no cover)
Jean Wilson & Friends @ Monument Park (Dexter) from 6:30-9pm (free at Dexter’s Summer Music Series)
Judy Banker Band @ Ann Arbor Downtown Library from 6:30-7:30pm (free)
Chase Rice & Ian Munsick w/ Zach John King at 6:45pm (ticketed event at the Chelsea Community Fair Summer Kickoff Concert)
Pontiac Trail Blazers ft. Erin Zindle @ North Star Lounge from 7-10pm ($) 
Bob Skon Trio @ Ypsi Alehouse at 7pm (no cover)
Jocelyn Gould Quintet ft. Randy Napoleon @ Blue Llama Jazz Club from 7-8pm & 9:30-10:30pm ($)
Whiskey A Go-Go, Spellbound, Concrete Angels, General 11 @ The Blind Pig, doors at 7pm ($)
Third Coast Swing @ Kerrytown Concert House at 7:30 pm ($)
Leaving Lifted @ The Rumpus Room (Chelsea) at 8pm ($10)
Mike Massé @ The Ark at 8pm ($35)
Spark @ Revel Run (Chelsea) from 8-10pm (no cover)
She-Bop @ Zal Gaz Grotto from 8-11pm ($) 
Rick Burgess Trio @ The Earle from 8-11pm (no cover)
Elspeth Tremblay & The Treatment, The Antibuddies, Dyzioek @ Ziggy’s (Ypsi) at 8pm ($10)
The Machine @ Mash (Ypsi) at 8pm (no cover)
Rob Crozier Ensemble @ The Habitat Lounge from 9-11pm (no cover)
No Conflict @ Ypsi Alehouse at 9:30pm (no cover)
Cloudhoppers @ Mash (Ann Arbor) at 10pm (no cover)

Saturday, May 31st:
Irish Session w/Irish-ish @ Ypsi Alehouse at 1pm (no cover)
Irish-ish @ Ypsi Alehouse at 4:30pm (no cover)
Aaron Johnson @ Mash (Ann Arbor) @ 6pm (no cover)
Elisabeth Pixley-Fink @ North Star Lounge from 6-7:15pm ($)
Demetrius Nabors @ Blue Llama Jazz Club from 6:30-7:30pm and 9-10pm ($)
Steve Taylor @ The Highline Room (Dexter) from 7-10pm (no cover)
Lynne Frederickson @ 4M Venue from 7-9:30pm (no cover)
Kandy Fredrick & Cameron Getto @ Ypsi Alehouse at 7pm (no cover) 
Rick Burgess Trio @ The Earle from 8-11pm (no cover)
Joshua Davis & Brad Phillips @ The Ark at 8pm ($29)
Same Eyes, Bandeau, Cowgirl @ Ziggy’s (Ypsi) at 8pm ($) 
Shelby & Jake @ Mash (Ypsi) at 8pm (no cover)
The Mighty Swells @ The Rumpus Room (Chelsea) at 8pm ($15)
The Extrusions @ Zal Gaz Grotto from 8-11pm ($)
Good Man's Brother w/ Hillbilly Knife Fight, Failing As Humans, Sick Smile @ The Blind Pig, doors at 8pm ($)
Rob Crozier Ensemble @ The Habitat Lounge from 9-11pm (no cover)
Full Tilt Boogie @ Mash (Ann Arbor) at 10pm (no cover)
Jacob Hart Quintet @ Blue Llama Jazz Club from 10:30-11:45pm ($)

Sunday, June 1st:
Sandra Bomar Quintet @ Blue Llama Jazz Club from 6-7pm & 7:30-8:30pm($)
Mass Dispute, Perfect Average, Staircase Joke, Reckless Manner, Mr. Davis @ Blind Pig, doors at 7pm ($14.30)
Miles Nielsen & The Rusted Hearts @ The Ark at 7:30pm ($29)

Monday, June 2nd:
Keaton Royer and Josef Deas @ Weber’s from 6-9pm (no cover)
Paul Keller Orchestra @ Zal Gaz Grotto from 7-10pm ($)
Blank Hellscape, Aaron Dilloway, Fred Thomas, Pod Blotz @ Ziggy’s (Ypsi) at 8pm ($)
Eric Johanson @ The Ark at 8pm ($29)

Tuesday, June 3rd:
Easy Street Jazz Band @ Zal Gaz Grotto Club from 5-7pm ($) 
Keaton Royer and Josef Deas @ Weber’s from 6-9pm (no cover)
Jake Reichbart @ The Earle from 7-9pm (no cover) 
Reverie Road @ The Ark at 8pm ($29)

Wednesday, June 4th: 
Ryan Brandenberg @ North Star Lounge from 5:30-6:30pm (no cover)
Keaton Royer and Josef Deas @ Weber’s from 6-9pm (no cover)
Magnolia Rohrer, Prof. Leonard King’s Proportioned Orchestra @ Ann Arbor Hands-On Museum at 7pm (ticketed event by Third Place MusicFest 2025)
Chelly K @ Blue Llama Jazz Club from 7-8pm & 8:45-9:45pm ($) 
Jake Reichbart @ The Earle from 7-9pm (no cover) 
Intentions w/ Save Someone, Azura, Flatroom @ The Blind Pig, doors at 8pm ($)

And if you haven’t already… make sure you follow me on Instagram to get more updates & ideas of things to do and see in the area! 

👋🏻 Who Am I?

Hi! I’m Bailey Walsh. 🤗 I’m a Realtor in the area & a lover of all things local. I hope this newsletter helps you explore some new places, make new connections & have a little more fun!

And don’t hesitate to reach out if I can ever help you with any real estate needs in Ann Arbor, Dexter, or any of the surrounding areas!

💙 THANK YOU!

Thanks for reading the AA Insider this week!

If you enjoyed it enough to share it with someone else, that would make me super happy too 🙂