Heirloom Tomato Salad with Pickled Fennel and Chilies

This is a farmer’s market fever dream of a salad. It contains some of the greatest hits of late summer! The pickled, sour fennel plays gorgeously off of the super sweet heirlooms. And nobody would hate you if you added some salty aged cheese into the mix.


Pickled fennel:

  • 1 medium fennel bulb, cored, thinly sliced
  • 1 1/2 cups unseasoned rice vinegar
  • 1/2 cup sugar
  • 2 tablespoons kosher salt


  • 2 pounds large heirloom tomatoes (about 3), cut into wedges
  • 1 cup cherry tomatoes, preferably heirloom, halved
  • 2 tablespoons white balsamic or Sherry vinegar
  • 7 tablespoons extra-virgin olive oil, divided
  • Kosher salt, freshly ground pepper
  • 2 Cubanelle peppers or Anaheim chiles, sliced into 3/4" rings, seeded
  • Fennel fronds (for serving)
  • Fresh basil (for serving)


For pickled fennel:
Bring vinegar, sugar, salt, and 1/2 cup water to a boil in a medium saucepan, stirring to dissolve sugar and salt. Pour vinegar mixture over fennel and let cool; discard sachet. Cover fennel and chill at least 12 hours.

For assembly:
Combine large and cherry tomatoes, vinegar, and 6 tablespoons oil in a medium bowl; season with salt and pepper. Let sit at room temperature 30 minutes.

Before serving, heat remaining 1 tablespoon oil in a medium skillet over high heat. Cook Cubanelle peppers, tossing often, until charred in spots, about 4 minutes.
Serve tomato salad topped with peppers, pickled fennel, fennel fronds, and basil.

About the Chef

Stephanie Goldfarb is a Chicago-based chef and national food television personality specializing in seasonal, globally-inspired cuisine. Recognized as the winner of Food Network’s America’s Best Cook competition, and a celebrity chef on Kitchen Inferno and NBC’s Food Fighters, Goldfarb delivers unique and relatable culinary experiences to discriminating and casual diners alike. As the owner of the successful Seven Species Supper Club & Catering, she enjoys the challenge of building brand new menus each month that inspire both repeat clients and newcomers, and seeks opportunities to utilize new ingredients, techniques, and approaches in accessible ways.