New Bookstore & Cafe in Dexter + More Fall Fun and Live Music

September 26th-October 1st, 2025: Your local guide to the local events & live music happening this weekend in Ann Arbor, Dexter, Ypsi, Chelsea & beyond!

Author

Bailey Walsh
September 26, 2025

In partnership with

Hi neighbors!

Zach Bryan’s about to pack 100,000 people into The Big House 🎸… but if shoulder-to-shoulder cowboy hats aren’t your vibe, don’t worry. This weekend has everything from haunted hayrides to coffee raves, fall markets, and plenty of other live music. Let’s get into it!

📰  What’s New?

Courageous Books & Café | Dexter
Dexter’s newest hangout spot is here! Courageous Books is celebrating its grand opening Friday, Sept 26 at 8063 Main St. Come for the shelves, stay for the sips.

🗓️ What’s Happening?

Looking for things to do in Ann Arbor, Dexter, Ypsi & beyond this weekend? 

Drip & Drop Coffee Rave | Dozer Coffee | Sat, Sept 27 | 9am–12pm
☕ A silent disco with your morning coffee? Pure Ann Arbor. House/lofi DJs, vendors & giveaways.  

Webster Fall Festival | Sat, Sept 27 | All day
🍂 Old-school fun with hayrides, sheep herding, blacksmith demos, local eats & live music.

Family Fright Fest | Ann Arbor | Sat, Sept 27 | 11am–7pm
🎃 Haunted hayrides, creepy carnival vibes & family fun.

Live Music + Food Trucks @ Hear.say Brewing Sat, Sept 27 | 2–5pm
🍔 Smash burgers, craft drinks, lawn games + live tunes from FeRn Whale before Zach Bryan at The Big House.

Fall Market @ Revel Run Sun, Sept 28 | 2–5pm
🛍️ Shop local vendors, sip seasonal drinks & catch Amy Grace live.

❤️ Fundraiser Spotlight

If you want to join me in doing a little good this weekend, take a minute to check out this fundraiser for the Gaza Soup Kitchen.

A local community member (Kinder Better Community) has poured so much thought into organizing it, partnering with 30+ Dexter and Ann Arbor businesses who donated $3,000+ in prizes (valued $50–$500+). And while we shouldn’t need an incentive to give, your support also comes with the chance to win some amazing local goodies.

Raffle tickets start at $15, and every entry helps provide hot meals, relief, and dignity to families in crisis. Deadline is Oct 12.

🏠 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 in the area, 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)

Friday, September 26th
Down on Main Street Music Festival (Ann Arbor) from 4-10pm (free)
Mary Ann Kirt @ Ypsi Alehouse at 4:30pm (no cover)
Wind, Wood and Steel @ North Star Lounge from 5:30-6:30pm (no cover)
Terry Farmer @ Lake Forest Golf Club from 5:30-8:30pm (free)
The Steve Taylor Three @ Sam Hill from 6-9pm (no cover)
Mystery Hillbillies @ LIVE from 6:30-9pm ($)
Pontiac Trail Blazers ft. Wesley Fritzemeier @ North Star Lounge from 7-10pm ($) 
DJ Batz @ 4M Venue from 7-9:30pm (no cover)
Shahida Nurullah @ Blue Llama Jazz Club from 7-8pm & 9:00-10:00pm ($)
Spanish Love Songs w/ Bike Routes, Worlds Greatest Dad @ The Blind Pig, Doors at 7pm ($30)
Bark’s Tales @ Ypsi Alehouse at 7pm (no cover)
Bijan Taghavi – Jazz Reimaginings: A Solo Pianist’s Tribute to The Great American Songbook @ Kerrytown Concert House at 7:30pm ($)
Verdi’s Requiem - Detroit Symphony Orchestra and the UMS Choral Union @ U-M Hill Auditorium at 7:30pm ($)
John Craigie w/ Cristina Vane @ The Ark at 8pm ($35)
Ralph McKee Blues Band @ Zal Gaz Grotto from 8-11pm ($) 
Nobody’s Business @ Mash (Ypsi) at 8pm (no cover)
The Rob Crozier Ensemble @ The Habitat Lounge from 9-11pm (no cover)
Hard Candy @ Ypsi Alehouse at 9:30pm (no cover)
Cetan Clawson @ Mash (Ann Arbor) at 10pm (no cover)

Saturday, September 27th:
Ronald Shelton @ Ypsi Alehouse at 4:30pm (no cover)
Ann Arbor Jazz Fest @ First Congregational Church of Ann Arbor from 4:30-8:30pm and @ The Ravens Club from 8pm–12am (free)
Zach Bryan & John Mayer @ Michigan Stadium at 5pm ($)
Joe Hassell @ Sam Hill from 6-9pm (no cover)
The Martians w/ Sins of Madness, Unholy Honor @ The Blind Pig, doors at 6pm ($14)
Delta 88 @ North Star Lounge from 6:30-7:45pm
Sean Dobbins & The Collegiate Collage @ Blue Llama Jazz Club from 6:30-7:30pm and 8:30-9:30pm ($)
Andrés Soto @ 4M Venue from 7-9:30pm (no cover)
Three Mirrors: Excursions in Collaboration hosted by Fred Thomas @ Ypsilanti Freighthouse at 7:30pm ($)
Strawberry Lake + Telephone Poles @ The Rumpus Room (Chelsea) at 8pm ($10)
Willi Carlisle w/ The Lowest Pair @ The Ark at 8pm ($29)
Normal Park, Ness Lake, Loudfoxcult, Marto.Matic @ Ziggy’s (Ypsi) at 8pm ($) 
The Reason You Came @ Mash (Ypsi) at 8pm (no cover)
Rachmaninoff Piano Concerto No. 2 @ U-M Hill Auditorium at 8pm ($)
Blue Custers @ Zal Gaz Grotto from 8-11pm ($)
Electric Rodeo Dance Party @ The Blind Pig, doors at 9pm ($21-$25)
Schmaltz @ North Star Lounge from 9-10:15pm ($)
Mike May & The Messarounds @ Mash (Ann Arbor) at 10pm (no cover)
Andrew Rathbun & Gary Versace @ Blue Llama Jazz Club from 10:15-11:45pm ($)

Sunday, September 28th:
Jason Quick @ Venue 4M from 11am-2pm (included with brunch) 
Steve Somers and Friends @ Ypsi Alehouse at 2pm (no cover) 
DJ Batz @ Sam Hill from 4-8pm (no cover)
Ann Arbor Jazz Fest @ First Congregational Church of Ann Arbor from 4:30-8:30pm and @ The Ravens Club from 7pm–10pm (free)
Phil Ogilvie's Rhythm Kings @ Zal Gaz Grotto from 5-8pm ($)
Anthony Stanco @ Blue Llama Jazz Club from 6-7pm & 7:30-8:30 pm($)
Scott Miller @ The Ark at 7:30pm ($29)

Monday, September 29th:
Paul Keller Orchestra @ Zal Gaz Grotto from 7-10pm ($)
Selwyn Birchwood @ The Ark at 8pm ($29)

Tuesday, September 30th:
Easy Street Jazz Band @ Zal Gaz Grotto Club from 5-7pm ($) 
Edgefest Warmup - Ken Kozora, Piotr Michalowski, Kenn Thomas, Shoskke-Rayzl Yuni and Deanna Relyer @ Ziggy’s (Ypsi) at 8pm (tips/donations appreciated)

Wednesday, September October 1st: 
Michelle Held @ North Star Lounge from 5:30-6:30pm (no cover)
Tiffany Gridiron Trio @ Blue Llama Jazz Club from 7-8pm & 8:30-9:30pm ($) 
Bill Hunt @ The Village Tap (Manchester) from 7-10pm (free)
Stacey Ryan w/ The Collarbones @ The Blind Pig, doors at 7pm ($)
American Aquarium w/ Collin Nash @ The Ark at 8pm ($29)

This weeks’ newsletter is sponsored by: Brad’s Deals

Clicking these sponsored ads helps support what I do — so, thanks in advance if you tap that. ⬇️

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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! 

💙 THANK YOU!

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