Crispy Winter Squash Caesar Salad

Executive Chef Gregory Wiener of Inn at Perry Cabin on Maryland's Eastern Shore shares an elegant autumn salad featuring pickled plums and a twist on a Thanksgiving staple

Delicata Squash Caesar Salad with Pickled Plums

“Our Delicata Squash Caesar Salad takes what many consider an autumn staple, hard squash, and turns it on its head. The salad is light and crisp from the pickled plums, yet creamy and unctuous from the dressing on the tatsoi greens. It is a great modern twist on a classic—a real crowd pleaser and head turner.” — Executive Chef Gregory Wiener, Inn at Perry Cabin

Chef Wiener sources delicata squash, a variety of winter squash, locally from Baywater Farms. Plums are one of the crops that the inn grows on its on-site orchards in St. Michaels, Maryland.

Delicata Squash Caesar Salad

Serves 4


  • 4 ounces delicata squash, thinly shaved and fried crisp*
  • 2 Pickled Plums (recipe follows), sliced into fourths
  • 8 ounces tatsoi or your favorite hearty greens
  • 4 tablespoons Caesar Dressing (recipe follows)
  • 3 tablespoons shaved Parmesan cheese
  • 1 tablespoon lemon zest
  • 20 canned Sweety Drop peppers
  • 20 croutons
  • Salt and pepper to taste


1 | Combine all ingredients in a stainless steel bowl; toss gently, being careful not to break up squash. Place neatly in desired serving vessel. Serve immediately.

*To fry squash, heat grapeseed or canola oil (enough to submerge squash slices) to 325°F in a deep pot. Add squash; fry until crispy.

Pickled Plums


  • 3 cups water
  • 2 cups red wine vinegar
  • 1 cup sugar
  • ¼ cup kosher salt
  • 4 star anise pods
  • 1 teaspoon pink peppercorns
  • 1 cinnamon stick
  • 3 pounds plums, cut in half, pits removed


1 | Bring water, vinegar, sugar, salt, star anise, pink peppercorns, and cinnamon to a boil in a pot. After boiling for 1 minute, remove from heat; allow to steep for 10 minutes. Place plums in a large bowl. Pour warm mixture over plums, and allow to cool, uncovered, for 4 to 6 hours. Cover, label, date, and store in refrigerator.

Caesar Dressing


  • 1 cup mayonnaise
  • 1½ teaspoons Worcestershire sauce
  • ½ cup freshly grated Parmesan cheese
  • ½ teaspoon kosher salt
  • ¼ teaspoon ground black pepper
  • 1½ teaspoons anchovy paste
  • 1.25 ounces lemon juice
  • 1½ teaspoons Dijon mustard
  • 1 garlic clove, finely minced


1 | Combine all ingredients. Cover, label, date, and store in refrigerator.

Recipe by Executive Chef Gregory Wiener of Inn at Perry Cabin