Sunday morning after the Dexter Summer Festival, the folding tables in Monument Park get stacked, the gazebo speakers get coiled into their cases, and Broad Street goes back to being a regular street. If you walked through downtown that morning, you'd assume the town's big event of the summer had come and gone.
Two days later, easels start showing up on the same sidewalks. Not festival organizers this time. Painters. Because while the Chamber of Commerce is still tearing down from one event, the Dexter Arts, Culture and Heritage Committee is setting up the next one, and by October the Lions Club will run a third. Nobody who lives here thinks of this as one long festival season. It's actually three separate organizations passing a baton through the same park, and knowing which group is running which leg changes how you plan your fall.
Two "Dazes," Not One
Here's the mix-up that trips up even longtime residents. The event that just wrapped on August 7 and 8 used to be called Dexter Daze. The Dexter Area Chamber of Commerce rebranded it the Dexter Summer Festival a few years back, though plenty of people still call it by the old name out of habit.
That's a different event from Apple Daze, the Lions Club's fall festival that lands in October. Same rhyme, same park, completely different organizers, completely different scale. If a neighbor tells you they're headed to "Daze" in October, they don't mean the one that just happened.
Three Groups, One Park
Once you separate the names, the mechanism becomes clear. Three volunteer organizations each run their own signature event through Monument Park on a rough eight-week rotation, and none of them are coordinating a shared calendar. That's exactly why the park never really sits empty between late summer and Halloween.
| Event | Who runs it | When | Where in town | How you'll know it |
|---|---|---|---|---|
| Dexter Summer Festival (formerly Dexter Daze) | Dexter Area Chamber of Commerce | First weekend of August | Monument Park, a second stage at Broad and Grand, and Mill Park | Fireworks, a Saturday parade, dueling live music stages |
| Paint Dexter Plein Air Festival | Dexter Arts, Culture and Heritage Committee | Mid-August | Monument Park's Tent Gallery and Mill Creek Park | Easels on public sidewalks and a timed Quick Draw contest |
| Apple Daze | Dexter Lions Club | Early October (2026 date not yet announced) | Monument Park, with hayrides out to Dexter Cider Mill | Apple pie eating contest, pumpkin bowling, craft booths |
What Just Wrapped
The Summer Festival ran the way it usually does. Friday brought a classic car show downtown and a fireworks display at dusk, sponsored by a local business, while the Monument Park gazebo carried live music from Outbound Packard in the afternoon and the Detroit blues act Randy Brock into the evening. A second stage at Broad and Grand ran its own lineup in parallel, with the Gravel Shakers playing blues and rockabilly and the Step Aside Band closing with honky tonk and country originals, according to the Ann Arbor Observer's event coverage.
Saturday opened with the parade at 10 a.m., kids on decorated bikes leading the way, then settled into a full day of cornhole, mini golf, and a dunk tank at Monument Park while Mill Park handled the bounce houses and balloon animals. The weekend closed with an outdoor screening of The Princess Bride at the Dexter Amphitheater on Jeffords and Alpine, right by the condos there.
What's Actually Happening This Week
While the Summer Festival gear was still being packed up, the next handoff was already scheduled. The Paint Dexter Plein Air Festival, organized by the Dexter Arts, Culture and Heritage Committee, runs this year from August 10 through 15, meaning it's underway as you read this. This is not a booth-and-vendor event. Painters work outdoors around town, in Mill Creek Park and along the sidewalks downtown, and the whole thing has run every summer since 2013, according to the City of Dexter's public art page.
If you're around Friday, that's when the Quick Draw happens: artists are given a fixed window to complete a piece outdoors, and the Tent Gallery in Monument Park opens that afternoon so you can see the results and buy them on the spot. It's a genuinely different pace than the Summer Festival crowd. Fewer speakers, more easels, and it rewards a slower walk through downtown rather than a full day planted at one stage.
Grabbing a Bite Between Events
Downtown's food scene has turned over enough in the past couple of years that it's worth an update if you haven't been paying attention. Dexter Brunch House opened at the corner of Main and Alpine in February 2025, taking over the space that had been the longtime Dexter Riverview Café. It's open daily from 7 a.m. to 3 p.m., leaning on scratch-made items like sausage gravy and fresh-squeezed orange juice, and it's become the obvious stop for anyone catching the Paint Dexter Quick Draw before it wraps up in the afternoon.
Further down Ann Arbor Street, 42 North Social House moved into a nineteenth-century Arts and Crafts farmhouse, one built by a president's brother, that had previously housed the Fillmore Bar and Grill. Owners Andy Copp and Jamie Schmunk added fire pits outdoors and a weekday social hour from 4 to 6 p.m. with small plates running $3 to $9, according to the Ann Arbor Observer's writeup of the reopening. And the Beer Grotto has anchored downtown since 2013, pouring from a rotating lineup of 48 drafts, useful to know if you want to wait out a festival crowd somewhere quieter.
None of these openings were timed to the festival calendar on purpose, as far as anyone's said publicly. But the effect is that downtown now has more places built for sitting down and staying awhile right as its event schedule got busier, not less.
Looking Ahead to Apple Daze
The Lions Club hasn't set this year's date yet, but the format has been consistent enough in recent years to plan around loosely. Last year's Apple Daze ran the first Saturday in October at Monument Park, with hayrides out to the Dexter Cider Mill, an apple pie eating contest, pumpkin bowling, and for the first time, putt-putt golf.
"We just want to give families a chance to come into town, spend the day, and enjoy themselves," Dexter Lion Dave Steptoe told the Sun Times News ahead of last year's event. "It's a way for us to support local businesses, showcase the crafters, and put on something fun for everybody as we head into fall."
The festival also funds the Lions' community work, including their KidSight program, which offers free vision screenings for kids using specialized cameras. And the same evening, the Arts, Culture and Heritage Committee typically follows with S'mores N' More back at the gazebo, an open-mic style wind-down that turns the same stage that hosted apple pie contestants into an evening of community performances.
The Park Doesn't Actually Rest
Stack it all up and the pattern holds even outside these three headline events. The Dexter Summer Music Series brings bands to the Monument Park gazebo on Friday evenings in late spring, and the city's rotating outdoor sculpture display, the Dexter Art Gardens, keeps new work on view around downtown year-round. The park isn't hosting a series of unrelated events. It's the same six or seven acres being handed continuously between three volunteer groups who happen to like the same gazebo.
If you're the kind of resident who checks the calendar the week before something happens, you'll keep catching Dexter mid-transition, tables coming down as easels go up. If you know it's a relay instead of a lineup, you can actually plan around the parts that matter to you.
If you're weighing whether Dexter's the kind of town you want to be even closer to, or you're already here and curious what your home might be worth in a market that keeps drawing people to a downtown this busy, The Darby Group knows this neighborhood block by block. Take a look at our Dexter neighborhood guide or request a free home valuation whenever you're ready to talk specifics.
