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New Dexter Winery, Carnivals, Big Play Day, Live Music & More
June 20th-25th 2025: Your local guide to the local events & live music happening this weekend in Ann Arbor, Dexter, Ypsi, Chelsea & beyond!
Hi neighbors!
This week brings carnivals, firetruck sprays, garage sales, Big Play Day at the Arb, live music, and more—there’s no shortage of fun around Ann Arbor, Ypsi, Dexter, and Chelsea this weekend.
Oh, and did you hear that Dexter’s getting its very own vineyard soon?! Yep… we’re about to get fancy. 🍷
📰 What’s New?
🍷 Coming Soon: Social Vines Winery in Dexter

A new winery is (literally) taking root just outside Dexter—and it’s not your average tasting room.
Built on 70 acres of former gravel pit turned sustainable vineyard, Social Vines is the dreamchild of local couple Lori and Brian Herron, and it's all about community, cold-hardy grapes, and creating a place to just be.
Expect local collabs, live music, picnic tables with views, and wine that doesn’t take itself too seriously. Follow them on Instagram for updates.
🎆 SAVE THE DATES!:
Fourth of July Fireworks at Social Vines — Pre-registration required + wine will be available for purchase for the first time during the event!
Soft Opening – July 11 (Tasting room opens with wine by the glass, bottles, and charcuterie)
🗓️ What’s Happening?
Looking for things to do in Ann Arbor, Dexter, Ypsi & beyond this weekend?
🎡 Dexter Summer Carnival | June 19–21 – Dexter
Head to the Dexter Legion for rides, games, and small-town carnival charm hosted by Wade Amusements (the same group that did last year’s Bicentennial carnival!)
🎟️ Ann Arbor Jaycees Summer Carnival | June 19–22
Wristbands, ride tickets, and all the spinning rides your stomach can handle this weekend at Pioneer HS!
🛍️ Thornton Farms Neighborhood Garage Sale | June 20–22 – Dexter
You know what’s better than a garage sale? A lot of them right next to each other. Thornton Farms is hosting a massive neighborhood-wide sale all weekend long.
🚜 Touch-a-Truck at Revel Run | June 20, 4–6:30 PM – Chelsea
Big trucks + little humans = guaranteed win. Check out cool vehicles, tractors, and end the night with a Firetruck Spray at 6 PM.
🌿 Big Play Day at Nichols Arboretum | June 21, 10 AM–2 PM – Ann Arbor
A free, family-friendly event full of nature-based exploration and guided play in one of Ann Arbor’s most beloved green spaces.
🐝 Pollinator Day at Domino’s Farms | June 21, 10 AM–3 PM – Ann Arbor
Hosted by A2B2 Beekeepers, this event includes live honey extraction, honey tasting, crafts, food trucks, and plenty of bee facts. Admission: $8 (discounts for seniors/kids).
🎶 Ann Arbor Summer Festival – Top of the Park | Through June 29 – Downtown AA
Movies under the stars, live music, food vendors, comedy, and more—all for free at the beloved A2SF. It runs nightly on Ingalls Mall, and it’s a local summer staple for a reason.
🏠 Thinking about making a move in the Ann Arbor area?
![]() | Hi! I’m Bailey Walsh 👋 Whether you're planning a move or just Zillow-scrolling at midnight with a glass of wine, I’m always happy to help. Reach out anytime—whether you’ve got a real estate question or just need a solid coffee rec, I’ve got you. |
🎵 Live Music Lineup
(Live music events in Ann Arbor/Ypsi unless otherwise noted & those marked with ($) charge a cover or require a ticket to the best of my knowledge)
🎶 Free Outdoor Live Music in Downtown Ann Arbor
Date | Performer | Location | Time |
---|---|---|---|
Thu, June 20 | Gabriel Brass Band | Top of the Park | 7:00 PM |
OKAN | Top of the Park | 8:45 PM | |
TBD | Washington (by Echelon) | 7:00–9:00 PM | |
TBD | Liberty (by Ann Arbor Art Center) | 7:00–9:00 PM | |
Fri, June 21 | Camilla Cantu | Top of the Park | 5:00 PM |
Marbrisa | Top of the Park | 6:15 PM | |
Mexicuba | Top of the Park | 7:00 PM | |
Armando Vega & the 313 Orchestra | Top of the Park | 8:45 PM | |
Blue Angels Meet & Greet | Main St (by Conor O’Neill’s) | 7:00–8:00 PM | |
DJ Ron Don | Main & Liberty Intersection | 7:00–9:00 PM | |
Sat, June 22 | Fangs and Twang | Top of the Park | 5:00 PM |
GEMILY | Top of the Park | 6:00 PM | |
Balkan Paradise Orchestra | Top of the Park | 7:30 PM |
Friday, June 20th:
Swamp Rats @ North Star Lounge from 5:30-6:30pm (no cover)
The Non-Prophits @ Ypsi Alehouse at 6:30pm (no cover)
Bernadette Catherine @ Monument Park (Dexter) at 6:30pm (free)
Pontiac Trail Blazers ft. Grant Flick @ North Star Lounge from 7-10pm ($)
DJ Batz @ 4M Venue from 7-9:30pm (no cover)
The 2025 Detroit Jazz Festival All-Stars Generation Sextet @ Blue Llama Jazz Club from 7-8pm & 9:30-10:30pm ($)
The Bends (Radiohead Tribute) @ The Rumpus Room (Chelsea) from 7-11pm ($10)
Great Lakes Chamber Music Festival: Festival-in-Residence #2 @ Kerrytown Concert House from 7:30-9pm ($)
Good Man’s Brother, Sonic Smut, Ghost Pipe @ Ziggy’s (Ypsi) at 8pm ($10)
Cris Jacobs w/ Lost Mary @ The Ark at 8pm ($29)
Atomic Cafe @ Zal Gaz Grotto from 8-11pm ($)
Cowgirl @ Ypsi Alehouse at 9pm (no cover)
The Rob Crozier Ensemble @ The Habitat Lounge from 9-11pm (no cover)
Saturday, June 21st:
Out Loud Chorus @ The Ark at 1pm (free)
Fernwood Underground @ Ypsi Alehouse at 4:30pm (no cover)
Schmaltz @ North Star Lounge from 6:30-7:45pm
Sean Dobbins Quintet @ Blue Llama Jazz Club from 6:30-7:30pm and 9-10pm ($)
Amy Grace @ The Highline Room (Dexter) from 7-10pm (no cover)
Rachel Arnsdorf @ 4M Venue from 7-9:30pm (no cover)
Set To Spiral w/ Miseracord, Flowers on the Grave, Death Arcana @ The Blind Pig, doors at 7pm ($14.30)
Wilson & Brenner @ Ugly Dog Distillery (Chelsea) at 7pm (no cover)
Billy Mack & The Juke Joint Johnnies @ The Rumpus Room (Chelsea) at from 7-11pm ($15)
Darlingside w/ Clovers Daughter @ The Ark at 8pm ($40)
Andrew Wooten, Elephant Den, Sock Jock @ Ziggy’s (Ypsi) at 8pm ($10)
Spark @ Zal Gaz Grotto from 8-11pm ($)
The Sound of Pride: A Musical Themed Drag Cabaret @ North Star Lounge from 9-10:15pm ($)
Noah Hogan Quartet @ Blue Llama Jazz Club from 10:30-11:45pm ($)
Sunday, June 22nd:
Laura Brand French @ Venue 4M from 11am-2pm (included with brunch)
Steve Somers and Friends @ Ypsi Alehouse at 2pm (no cover)
Concert to Benefit Lost Voices: A Tribute to Josh White, Jr. @ Kerrytown Concert House at 4pm ($)
Phil Ogilvie's Rhythm Kings (P.O.R.K.) @ Zal Gaz Grotto from 5-8pm ($)
An Evening with William Hill III @ Blue Llama Jazz Club from 6-7pm & 7:30-8:30 pm($)
Birdtalker w/ Curtis Ford @ The Ark at 7:30pm ($29)
Monday, June 23rd:
Paul Keller Orchestra @ Zal Gaz Grotto from 7-10pm ($)
Tuesday, June 24th:
Easy Street Jazz Band @ Zal Gaz Grotto Club from 5-7pm ($)
Jake Reichbart @ The Earle from 7-9pm (no cover)
Summerween Jazz w/ Jon Hammonds’, Galen Bundy, and Cory Tripathy @ Ziggy’s (Ypsi) at 8pm (tips/donations appreciated)
Half Gringa @ The Ark at 8pm (free)
Wednesday, June 25th:
Captain Karnooba presents The Secret Outer Space Radio Hour @ North Star Lounge from 5:30-6:30pm (no cover)
Jean Wilson & Friends @ Blue Llama Jazz Club from 7-8pm & 8:45-9:45pm ($)
Jake Reichbart @ The Earle from 7-9pm (no cover)
Runnin' on Blues @ Ypsi Alehouse at 7pm (no cover)
Shane Guerrette w/ James Bourland & The Staches @ The Blind Pig, doors at 7pm ($19.80)
Citizen Jones, The Revelators @ Ziggy’s (Ypsi) at 8pm ($)
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!
💙 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 🙂