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Roasted Squash, Chestnut, and Chicory Salad with Cranberry Vinaigrette

This roasted squash, chestnut, and chicory salad is an elegant dairy-free dish that captures the very best flavours of the colder months. The natural sweetness of the roasted acorn squash and chestnuts provides a beautiful contrast to the slightly bitter notes of the fresh chicory. Finished with a warm, tangy cranberry vinaigrette and salty pancetta, it offers a sophisticated balance of textures and tastes that works perfectly as an impressive starter or a substantial lunch.

As a versatile seasonal recipe, this salad is ideal for autumn entertaining or as a festive side dish for a Sunday roast. The combination of colourful cranberries and golden squash makes it a visual centrepiece for any table. By using shop-bought cooked chestnuts, the preparation is kept simple, allowing you to focus on achieving that perfect golden colour on the squash and a satisfyingly crisp finish on the pancetta.

Continue reading below

Ingredients for Roasted Squash, Chestnut, and Chicory Salad with Cranberry Vinaigrette

  • 2 tablespoons extra-virgin olive oil plus additional for greasing

  • 450g acorn squash

  • 1 teaspoon salt

  • 1/2 teaspoons black pepper

  • 150g peeled cooked whole chestnuts (from a 7- to 8-oince jar), cut into thirds

  • 4 (1/4-inch-thick) slices pancetta (170g total), cut into 1/4-inch dice

  • 30g fresh cranberries, finely chopped

  • 1 tablespoon packed dark brown sugar

  • 60ml water

  • 2 tablespoons whole-grain mustard

  • 350g chicory (curly endive), trimmed and torn into 2-inch pieces (2400ml )

How to make Roasted Squash, Chestnut, and Chicory Salad with Cranberry Vinaigrette

Put oven rack in middle position and preheat oven to 232°C. Line a large shallow baking pan with foil and oil generously with olive oil.

Cut off stem end of squash, then put cut side down and halve lengthwise. Discard seeds, then cut squash into 1/2-inch-thick slices. Peel if desired with a paring knife and transfer slices to a bowl. Add 1 tablespoon olive oil, 1/2 teaspoons salt, and 1/4 teaspoons pepper and gently toss to coat. Arrange in 1 layer in lined baking pan and roast until golden, about 15 minutes. Remove from oven and turn squash over with a spatula. Add chestnuts to pan in an even layer, then continue to roast until squash is golden and tender, 10 to 15 minutes. Keep warm, covered with foil.

While squash is roasting, cook pancetta in a dry 10-inch heavy skillet over high heat until browned, about 4 minutes total. Transfer pancetta with a slotted spoon to paper towels to drain, reserving fat in skillet.

Reheat pancetta fat over moderately high heat until hot but not smoking, then add cranberries and brown sugar and stir once to combine. Remove from heat and add water, stirring and scraping up brown bits from bottom of skillet.

Transfer cranberry mixture to a medium bowl and whisk in mustard, remaining tablespoon olive oil, 1/2 teaspoons salt, and 1/4 teaspoons pepper.

Toss together chicory, roasted acorn squash, and chestnuts. Just before serving, toss with dressing and sprinkle with pancetta.

Disclaimer

While every effort has been made to ensure the information is accurate and up to date, individual needs may vary and dietary requirements can differ based on personal health conditions. Always check food labels and allergen information before preparing or consuming any recipe. If you have specific health concerns, allergies, intolerances, or are following a medically prescribed diet, seek advice from your GP, pharmacist, or a registered dietitian before making significant changes to your diet or lifestyle.

Article history

The information on this page is peer reviewed by qualified clinicians.

  • 17 Jan 2026 | Originally published

    Authored by:

    UK recipe editors

    Peer reviewed by

    UK recipe editors
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