Late-Summer Weekends in Highland: Where Your Neighbors Actually Are in August

Every small town has one stretch of the calendar that does more social work than the rest of the year combined. In Highland, it isn't Schweizerfest in June, and it isn't the Christmas Parade. It's the two-week window between the last Municipal Band concert and the Sunday you carry a foil pan of fried chicken back to your car on Lemon Street. If you moved here from somewhere bigger, this is the stretch that finally makes sense of why people talk about Highland the way they do.

Here's the compressed calendar so you can plan the fridge magnet:

The Friday Square routine, before it goes quiet

The Downtown Square runs on a Friday rhythm most of the summer, and August is when it thins out. The Peanut Butter & Jam Festival on the Square runs Fridays from 11:30 a.m. to 1:00 p.m., with the last of the 2026 lineup landing on August 7. The pull isn't the sandwiches, which are free from Parks & Rec, but the fact that half your kid's school and a rotating cast of local vendors show up in the same block for ninety minutes.

At the other end of the same Fridays, the Municipal Band Concerts happen Fridays at 8 pm, mid-June through mid-August, on the Downtown Square, free to the public, and you bring your own lawn chair. Fifty musicians on the bandstand is not something most towns this size can field, and the last few concerts of the season tend to draw the biggest crowds because everyone knows the count is running out. If you've been meaning to bring the folding chairs down, the second and third Fridays of August are your window.

One practical note about the Square itself in August: the fountain runs, the benches are shaded by early evening, and parking off Main gets tight around 7:30 on band nights. Locals who've done this a few times park behind the businesses on Broadway and walk in.

Kirchenfest weekend: the actual center of gravity

If you've lived in Highland for more than a year, you already know Kirchenfest is the weekend that outranks the rest. If you're newer, understand the scale before you plan around it. Kirchenfest, German for "Church Festival," is one of the largest church festivals in Southern Illinois, with the event spreading over six acres on the grounds of St. Paul Parish, and the festival has run since 1970 with a German theme reflecting Highland's Swiss and German heritage. Six acres is not a euphemism. It's a small county fair squeezed onto a church campus, and the town reorganizes itself around it for three days.

2026 dates are August 21–23, and there are three moments inside that weekend worth planning your own around.

Saturday morning: the Strassenlauf

Before the tents open, there's a footrace. The St. Paul Strassenlauf offers 2 km, 5 km, and 10 km distances on Saturday, August 22, 2026, starting at 7:30 a.m. from St. Paul Catholic Church on Park Street. This is the one Kirchenfest event where the crowd skews toward people who live inside the 62249 ZIP rather than day-trippers from Edwardsville and Troy. If you want to meet the kind of neighbor who's been running the same 5K route for fifteen years, this is where they are at 7:45 on a Saturday.

Saturday afternoon and evening: the skillet

The Bavarian skillet stand is the closest thing Kirchenfest has to a signature. The mechanics of it are more interesting than the marketing suggests. The combined skillets cook 800 lbs of sausage, 1000 lbs of potatoes and 150 lbs of scrambled eggs every Kirchenfest, with each skillet serving about 40 at a time and feeding over 2,500 people; the original burners used water heater burners before an engineer designed a custom burner producing 250,000 BTU, enough to heat four 2,000-square-foot homes. The recipe took six months of experimentation to land on sausage, peppers, onions and sweet Bavarian kraut. That's the sort of detail nobody outside Highland knows, and it's why the line moves faster than it looks.

Sunday: the chicken dinner, and how not to wait

Sunday is chicken dinner day, and this is where people who've been coming for years quietly outmaneuver the first-timers. The Kirchenfest Chicken Dinner is available for carryout or drive-thru on the Sunday of the event.

For carryout, pick up your meal in the air-conditioned cafeteria by entering from Trinity Hall or the Lemon Street side entrance. For drive-thru, enter the line at 9th & Lemon Streets and they bring the meal to your car.

New for 2026: the "Side of Sides" option, which is everything from the dinner except the chicken, available in the carryout line only. If you have someone in the house who doesn't eat meat, or you just want extra of the fixings for a weeknight, that's the ordering line to know.

The other Kirchenfest facts worth having in your head: the two-day church festival offers food including the Bavarian dish prepared in a 500-pound skillet and a sit-down chicken dinner, live music, games, a competitive run, bike ride and much more, and it's the fourth weekend in August every year. You will hear people on the Square all summer say "we'll figure it out after Kirchenfest." This is what they mean.

What else is quietly running that same week

Two things overlap Kirchenfest weekend that get lost in the noise:

• Highland Muny Band's final Friday. The band concert calendar wraps mid-August, so the Friday before Kirchenfest is often the last one of the year. If you were going to make it to a band concert this summer, that's your final date on the board.
• Silver Lake Park in the last of the long light. Highland's lakefront park is where the weekend routine lives once the Square events wind down. The Family Night Hike at Silver Lake Park doesn't come until mid-September, but the trail is at its best in late August, and the parking lot next to the beach empties by 7:30 on a weekday evening.

For newer arrivals: what "everyone knows" that nobody tells you

A few practical things longtime Highland residents assume you already know:

1. The Baymont fills up. If family is coming in for Kirchenfest weekend, book early. There is one hotel in town, and locals will tell you the same thing they tell everyone: check for a short-term rental once the Baymont is full.
2. Parking around 9th & Lemon on Sunday afternoon is worse than the drive-thru line looks. The drive-thru moves. Street parking on 9th does not.
3. The Strassenlauf awards happen after the run at Kirchenfest itself, so you can register, race, shower, and be back in the tent by lunch without leaving the parish grounds.
4. The flea market and auction on Saturday morning are how a lot of Highland households pass along furniture and estate items. It's a decent read on what's moving through local homes in a given year, which is another way of saying it's a decent read on what people are downsizing out of.

Why this two weeks matters more than it looks

Highland is a town where 100% of the Schweizerfest profits are donated back to different organizations in the community, and Kirchenfest works the same way. The dollars you spend on a bratwurst and a bag of kettle corn stay inside the ZIP code. That's the mechanical answer for why the events feel different from a suburban food-truck festival. The social answer is simpler: the people you'll be neighbors with for the next twenty years are all in the same three-block area on the same two weekends. If you've been meaning to actually get to know your street, August is when the barrier to doing it is at its lowest.

That's also the quiet reason August real estate conversations in Highland tend to start after Labor Day. Nothing serious gets decided the week of Kirchenfest. It waits.

If you're settling into Highland and starting to think about what your next move in the area looks like, whether that's a first home near the Square, a larger place closer to Silver Lake Park, or eventually a lot outside town, The Kehrer Team is a family-run local group that can talk through the market the same way we've talked through the August calendar here. When you're ready, contact your trusted real estate partners and we'll take it from there.