The Charlottesville 29

Where to eat in Charlottesville
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The 2025 Charlottesville 29: This Year’s List of Charlottesville’s Essential Restaurants

The 2025 Charlottesville 29 is here.

Each year, The Charlottesville 29 answers: if there were just 29 restaurants in Charlottesville, what would be the ideal 29? Background here and here. Annual cuts become ever more difficult, as openings outpace closings. For each restaurant, the Charlottesville 29 includes a description of why it was selected and an ordering guide, with recommendations from each restaurant’s chef/owner and appearances in Five Finds on Friday.

With that: The 2025 Charlottesville 29.

03/31/2025

Guajiros Miami Eatery

114 10th St NW . Charlottesville, VA . (434) 465-2108
https://www.guajiroscville.com/

Why Guajiros Miami Eatery?

If you need a boost in Charlottesville, head to Guajiros Miami Eatery. No place brings more joy more quickly. The bright colors, the breezy space, the pulsing soundtrack, the food, the drink, and, best of all, the infectious enthusiasm of the Mayorga family. You know how excited your dog is when a human being arrives? Walk into Guajiros, and that’s how they seem to relish the opportunity to serve each guest.

A Miami eatery celebrating the Latin-American food that the Mayorga family grew up on, Guajiros is the realization of a dream. Initially, the Nicaragua-born family opened an order-at-the-counter space in a strip mall on 29N, focusing on their mother’s time-tested cooking. When that went well, they moved downtown in 2020 to launch a full-service restaurant serving breakfast and lunch. And, in 2024, they culminated their vision by moving to their current location, adding dinner service, plus drinks in the expert hands of a Mayorga brother for whom spirits are a passion. Whoever said Disney Land is the happiest place on earth has never been to Guajiros.

What To Order

Guajiros’ brunch menu is available daily 8 am – 3pm, while dinner is 3 pm – 8 pm Wednesday through Sunday. Passion extends to the kitchen, so it’s hard to go wrong. Below are our picks and appearances in Five Finds on Friday, where a local chef or personality has named a Guajiros dish as one of the best in town.

Our Picks

  • Café con Leche
  • Buñuelos de bacalao
  • Tostones Rellenos
  • El Nacional
  • Lechon Mom’s Platter
  • Empanadas de Pollo
  • Pastelitos
  • Beignets
  • Bread Pudding with SugarBear Ice Cream
  • Dealer’s Choice

Five Finds on Fridays Picks

 

03/31/2025

Högwaller Brewing

1518 E. High Street . Charlottesville, VA. (434) 235-5043
https://www.hogwallerbrewing.com/

Why Högwaller Brewing?

Charlottesville’s Rivanna River corridor may be the smashburger capital of the world. It boasts masterpieces old and new. As for the old, while smashburgers are everywhere these days, there was a time when experts would scoff at cooks who press on their burgers. Nevermind. Riverside Lunch has been doing it that way for nearly a century, since long before chefs embraced the Maillard reaction of smashing burgers.

In 2023, Högwaller Brewing opened across the street, and while both joints make burgers worthy of The Charlottesville 29, what sets Högwaller apart are its modern enhancements of the smashburger experience. The grass-fed beef is from a farm just miles away, the rolls are baked locally, and the cooking method was perfected over time by chef and co-owner Tres Pittard and the late Wilson Richey. On top of that is beer brewed onsite by one of the world’s best, Mark Fulton. Put that all together and you have one of the most habit-forming places in town.

What to Order

While it would be unfair to call Högwaller Brewing a one-trick pony, the burgers and beers are clear standouts. Below are our picks as well as appearances in Five Finds on Friday, where a local chef or personality has named a Högwaller Brewing dish as one of the best in town.

Our Picks 

  • Junk Burger
  • Beer

Five Finds on Friday Picks