Fried Oreos, pupusas and a donut burger: Everything I ate at the Montgomery County Fair

I’ve been going to the Montgomery County Agricultural Fair every year since I was a baby. But through the years I haven’t ventured much outside my family’s favorite culinary tradition: grilled cheeses from The Big Cheese.

This year, I brought them along for opening night Friday, with the goal of trying as many foods as possible: a mix of fair favorites, creative additions and absurd concoctions. If my lingering stomachache is any indication, I’d say we succeeded.

Here are the good, the OK and the ugly of 15 food and beverage items I tried at the Montgomery County Agricultural Fair.

Fried Oreos

I’ve lived quite a few years successfully avoiding trying a deep-fried Oreo, but that streak ended Friday night.

Unfortunately, these are incredible.

When I entered the fair around 6:45 p.m., neon flashing lights advertising fried Oreos caught my eye right away. Golden-brown, piping hot from the deep fryer and cream melting on the inside, these made for a strong start to this crawl.

Hot Cheetos street corn

We meandered through mechanical bull rides and balloon dart games with stuffed animal prizes galore before landing on our second stop.

At a Mexican street corn booth, we opted for the street corn cup: creamy corn on the bottom, topped with equal parts parmesan, Hot Cheetos dust, crushed blue Takis and a lime wedge. Another solid choice.

Corn dog and fried pickles

I’m not sure if it’s just that I haven’t had a corn dog in forever or if the MoCo fair is home to the best corn dogs of all time. This one was great.

We also grabbed an order of fried sandwich-sliced pickles. I’m something of a fried pickle connoisseur and these were fine, but not anything I’d pick over our aforementioned samples.

Pupusas

These were an early front-runner among my group.

Masa stuffed with hot, melty cheese topped with a vinegar-soaked cabbage and salsa mixture. We were fighting over who got to finish this one.

Pulled pork sandwich, baked beans and coleslaw

If you arrive at the fair starving, Tailgators 2U serves heaping portions of barbecue classics done well.

I’d order this again, as long as there was a nearby picnic table open — not very well suited for eating while strolling around the fair.

Locally brewed beer

A nearby beer tent supplied beverages from Olney’s Lone Oak Farm Brewing Co. and Germantown’s Doc Waters Cidery. We went for the Lone Oak Montgomery Gold, an easy-drinking Pilsner made from locally grown barley that made for a refreshing accompaniment as we transitioned from the carnival half to the agricultural area.

Grilled cheese and lemonade

Visits to The Big Cheese at Ye Old Cheese Barn have been an annual tradition in the Yasharoff family my entire life. The grilled cheeses have the perfect bread-to-cheese ratio, with thinly sliced white bread cooked to a perfect golden brown, gooey orange Wisconsin cheddar in the middle and a pickle spear on the side. With a big cup of lemonade, we ate on a bench while listening to Harmony Express, a barbershop and a cappella-style chorus from Germantown.

A giant maple donut

The truck for Yoder’s Dutch Delights is tucked behind the Chilly Mall, home to the arts and crafts contest entries.

It offers fresh, Amish-style donuts. I had a bite of the maple, which was well worth the burgeoning stomachache.

Fried chicken

We arrived a bit late to Dickerson Market’s setup inside Heritage Hall, which technically closes at 8 p.m. but has a handwritten “or later” note on the hours posted on the door. I’m both bummed and grateful that we arrived when we did. All that was left were two tiny pieces of fried chicken: a kind of sad-looking leg and a wing. But at this point I was at an extremely uncomfortable level of full — I was not going to take more than one bite before passing any remaining dishes to the next person.

This fried chicken was so good I would have thrown out that rule in a heartbeat: crispy on the outside and juicy on the inside despite not being hot anymore. Dickerson’s will be my first stop on my next fair visit.

Ice cream

It was about time to call it a night, but I knew there were two more stops I needed to make before I could really say we got the full fair dining experience. The penultimate dish was a cake cone piled high with Caramel Caribou, the 2026 flavor of the year, a vanilla ice cream base with ribbons of caramel and mini chocolate-covered caramel cups. You can never go wrong with the Dairy Bar.

Krispy Kreme burger

I saved my white whale for last. Our newsroom was abuzz when I mentioned that the donut burger (also called a Luther burger) was on the menu at the fair this year. The thought of consuming another bite of food sounded terrible, but the thought of not being able to report back on a dish that sandwiches a beef patty, melted cheese, lettuce, tomato and bacon between two glazed donuts was worse.

So, on our way out, we made one more stop at the concession stand on the border of the agricultural section and the carnival area. The teenager at the counter told me they had sold “maybe one” other donut burger that day, which did little to boost my confidence in its quality.

This burger was bizarre: hot patty, cold tomato, sticky donut, bacon hanging on for dear life, slight unease about whether it was really safe to be consuming a leaf of romaine lettuce yet. Lest I suffer alone, my family members joined me in my misery, and each took a single bite to confirm: strange, confusing, not the best way to end a fun evening.

Even the goats in the barn next door agreed: It was baaaaaad.