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Who has the best grilled cheese sandwich in Bend, Oregon?

Downtown Bend Shopping

About a year ago, I embarked on a culinary journey to find Bend’s best mac & cheese. That blog post proved so popular with readers, and the mission so fulfilling to me as a food freak writer, that I decided to tackle another quest.

Possibly one of the most amazing grilled cheese sandwiches you’ll ever devour, the Grilled Cheesy at Crux Fermentation project.

With comfort food season in full swing, here’s your tasty overview of the best grilled cheese sandwiches in Bend.


The exotic twists

I’ll confess that this post was spawned by my boss gushing endlessly about The Grilled Cheesy on the menu at Crux Fermentation Project. Mystified by how an ordinary grilled cheese sandwich could spark such enthusiasm in a grown man, I decided to check it out for myself.

This is no ordinary grilled cheese sandwich. The Grilled Cheesy is an asiago-cheese crusted panini with mixed ricotta, pepper jack, and white cheddar with diced bacon and spicy pickles on Italian country spent grain bread from DiLusso Bakery. I wasn’t sure about the pickles and the bacon, but ohmyword this sandwich is amazing. The blend of textures and flavors is like nothing you’ve ever experienced in a sandwich, and I nearly wept with joy each time I took a bite. It’s $6 for half or $10 for a whole. Get the whole and pretend you’re going to share with a friend. Then eat the whole thing yourself, and wash it down with a pint of Crux’s own Long Day Imperial IPA.

Another great grilled cheese with a twist is the Grownup Grilled Cheese offered at GoodLife Brewing Co. This crusty beauty is served with thin-sliced apple, balsamic, roasted walnuts, aged white cheddar, and brie cheese. I love it best with a side of their to-die-for German potato salad and a pint of their Descender IPA.

A similar sandwich is available at the tucked-away hotspot Bend Mountain Coffee on Oregon Avenue in Downtown Bend. Their scrumptious Charity sandwich features brie, apple slices, toasted walnuts, and herbed olive oil on a crusty panini. They also offer another unique grilled cheese twist called the Pine Mountain. Besides Tillamook cheddar cheese, the sandwich includes basil pesto, roasted red peppers, spinach, tomato on a panini. Both are served with kettle chips or apple slices for $6.95.

For the serious gourmet, add suculent crab to your grilled cheese at Chow.

One of my favorite spots for breakfast and lunch is Chow, which is driven by a mission of sustainability and reliance on organic/locally-sourced food. Though you’ll find oodles of great choices on the menu, the best way to order is to request something special based on the chef’s imagination and what’s fresh that day. That’s how I ordered my grilled cheese, and I wasn’t disappointed. It was prepared on house made white bread with Cada Dia feta and white cheddar from Tumalo Farms. The chef added dill, garden tomato jam, and red crab meat, and served it with a side of sweet potato fries topped with bleu cheese. Unbelievable doesn’t even begin to describe it, and the flavors melded perfectly to create a supreme taste explosion. Those craving something a little more basic only have to say the word, and the chef will create something to suit your needs. The grilled cheese with crab runs $16, but take away the crab meat and you’re in the $10-12 range. No matter what you get, it’s guaranteed to be divine here.


Just like mom used to make

Not a fan of anything but the basic grilled cheese sandwich? Not a problem.

Caldera Grill in Downtown Bend does a terrific made-to-order grilled cheese sandwich. Take your pick among six kinds of cheese and five types of bread, or just let the chef choose for you. I opted for sourdough and regular cheddar, and was delighted with the crispy texture of the bread and perfect gooeyness of the cheese. What makes this sandwich extra special is ordering it with a side of Caldera’s to-die-for jalapeño corn chowder. At just $5.25 for a whole sandwich and cup of soup, you can’t beat this deal.

Another no-frills option with plenty of flavor is the grilled cheese at Planker Sandwiches in Downtown Bend. It’s made with Tillamook aged white cheddar on country bread, and served with a side of chips for just $6. Spend $8 to add a cup of their tasty tomato soup, and don’t forget to peruse the rest of their menu for a huge array of other scrumptious sandwiches.

One of my other favorite basic grilled cheese sandwiches is actually on the kids’ menu at Bend Brewing Company. I’ve been assured adults can order it without incident, but I’m sticking it in the next section just to keep things properly categorized.


The star of the kids’ menu

Oodles of Bend restaurants offer kids’ menus featuring simple grilled cheese sandwiches at a nice price. One of my personal favorites is at Bend Brewing Company (and not just because I love their Elk Lake IPA). The sandwich itself is basic and tasty, with cheddar and locally-made white bread for $3.99. It comes with fruit or fries, and while I’d normally suggest fruit for the sake of nutrition, the fries at BBC are too divine to resist.

A unique twist on the kids’ menu at Zydeco in Downtown Bend.

A favorite stop for my gentleman friend’s offspring is Pilot Butte Drive-In. Their kids’ menu has plenty of great options to choose from, but the grilled cheese is a family favorite, with extra-gooey goodness and fries and a cookie rounding out the meal for just $2.50.

Another kid favorite in the Old Mill District is Red Robin. Their super-cool kids’ menu with pictures and a wide array of side options is one of the best I’ve seen, and the $4.99 grilled cheese special is perfect paired with freckled fruit salad or mandarin orange slices and a bottomless beverage.

If mom and dad are craving something a bit more upscale, Zydeco in Downtown Bend is an awesome option. Their grilled cheese is served on a fresh, fluffy bun, and comes with a choice of fries or grilled veggies. The grilled veggies might be a problem for picky eaters, but for more adventurous eaters, they’re beautifully prepared with great flavor and a bounty of sweet potatoes, green beans, baby onions, and peppers. The price tag is $6 regularly, or show up on Sunday when kids eat free.

Another upscale option is Anthony’s in the Old Mill District. When we celebrated my birthday there in August, I was thrilled to see a well-rounded kids’ menu with plenty of choices for my gentleman friend’s offspring. Though the grilled cheese is a special-order option not shown on the menu, the Anthony’s staff is happy to make one with fresh white bread, plenty of cheddar and a choice of sides for just $3.99.

So that’s it for our roundup of Bend’s best grilled cheese sandwiches. Did we miss anyone? If so, please share! Who doesn’t need another excuse to pig out on cheesy goodness?

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