
This fancy stuffed butternut squash turns basic ingredients into an impressive dinner that'll wow your guests. The mix of sweet chestnuts, tangy cherries, and rich lentils builds amazing flavor that works perfectly with the natural sweetness in butternut squash.
I first whipped this up when some friends with different food restrictions came over for a holiday dinner. Everyone loved it so much that it's now my go-to special dish when I want something impressive without spending forever cooking.
Ingredients
- Butternut squash: 1-2 medium ones work as both container and part of your stuffing
- Olive oil: Gets the squash nicely browned and caramelized
- Brown onion: One chopped small adds the flavor foundation
- Garlic cloves: Three finely chopped for rich taste
- Fresh thyme: This herby flavor matches wonderfully with squash
- Cooked chestnuts: Add a sweet, buttery touch that makes this dish stand out from regular stuffed veggies
- Cooked quinoa: Gives nice texture and extra protein
- Cooked brown lentils: Make the dish filling enough to be a main course
- Dried cherries or cranberries: Add bursts of sweet-tart flavor
- Nutmeg: Just a tiny bit brings extra warmth
- Vegan butter: Adds creaminess without animal products
- Baby spinach: Brings color and nutrients while softening into the mix
- Sea salt and black pepper: Needed to bring out all the flavors
Step-by-Step Instructions
- Prepare the squash:
- Put your butternut squash on its side and cut it into 1½ inch thick circles. Take a small cookie cutter and push out the middle of each circle to make rings. Save the seeds and cut up the middle pieces you removed to use in the filling. If you don't have a cookie cutter, just use a spoon to dig out the centers.
- Roast the rings:
- Put the squash rings in a baking dish, add some olive oil, sprinkle with sea salt, and cook at 190°C for 20 minutes. This first cooking makes sure they'll be soft enough when the dish is done.
- Create the flavor base:
- While the rings are cooking, warm up olive oil in a big pan. Throw in garlic, onion and fresh thyme, then cook slowly for around 7 minutes until everything gets soft and smells amazing. This mix will flavor your whole filling.
- Build the filling:
- Toss in the chestnuts, dried cherries, and the squash pieces you saved with some vegan butter. Cook until the butter melts, then add a bit of nutmeg. This creates a wonderful mix of sweet, savory and earthy tastes.
- Incorporate the proteins:
- Mix in your cooked quinoa and lentils, and let everything cook together for another 5 minutes so the flavors can blend. The heat lets everything soak up all the tasty flavors you've built.
- Finish with freshness:
- Throw in the baby spinach and stir until it just starts to wilt. Add plenty of salt and pepper to taste. The spinach brings color, nutrients and freshness that balances the rich filling.
- Stuff and bake:
- Fill up each partly-cooked squash ring with lots of your filling mixture. Add a splash more olive oil on top, then put them back in the oven for 20-30 minutes until the squash is fully tender.
- Serve:
- Bring it to the table with vegan gravy and some tasty sides to round out your meal.

The chestnuts really make this dish special. I found out how good they were by chance when I had some left from another meal and just threw them in. Now I always keep some in my cupboard just for this. Their gentle sweetness and cool texture adds a surprise fancy touch that makes people think you spent all day cooking.
Make It Ahead
This dish works great when you need to cook early. You can fix the squash rings and filling up to two days before. When you're ready to eat, just put it all together and bake for the final 30 minutes. The flavors actually get better after sitting for a bit, so it's perfect when you want to hang out with your guests instead of being stuck in the kitchen.
Seasonal Adaptations
Butternut squash works best here, but you can use this yummy filling with other winter squashes too. Try smaller acorn squash for personal portions, or sweet delicata squash for a different flavor. During summer, stuff the same filling into bell peppers or hollowed-out zucchini for a lighter meal that uses what's fresh.
Serving Suggestions
For a meal that'll impress everyone, put these stuffed rings on some wilted greens with a little balsamic drizzle on top. Add a basic side salad with citrus dressing to brighten things up. This dish tastes great with a light red wine like Pinot Noir, or if you don't want alcohol, try a tart cranberry fizzy drink to match the flavors.

Make this dish when you want to wow someone, and enjoy all the different flavors and textures working together.
Frequently Asked Questions
- → Can I prepare this stuffed butternut squash ahead of time?
You bet! The squash rings and filling can be made up to 2 days early. Keep them apart in the fridge, then put together and bake when you're ready to eat. You might need to cook it 5-10 minutes longer if everything's cold from the fridge.
- → What can I substitute for chestnuts?
No chestnuts around? Try using toasted walnuts, pecans, or even crispy roasted chickpeas for a similar crunch. Each will add its own special taste to the dish while still giving you that nice texture difference from the softer stuff.
- → How do I know when the butternut squash is fully cooked?
Your butternut squash rings are done when a fork slides in easily with no pushing needed. The edges might also turn a bit brown and sweet-looking, which adds nice flavor and makes it look even tastier.
- → Can I use dried cranberries instead of cherries?
Sure thing! Dried cranberries work great instead of cherries and they're usually easier to find at stores. They give that same sweet and tangy kick that goes really well with all the savory stuff in the filling.
- → What sides pair well with stuffed butternut squash?
This dish goes great with roasted Brussels sprouts, fresh green beans, or a simple green salad. Don't forget that vegan gravy mentioned in the recipe, it adds lots of flavor. For fancy dinners, try adding some roasted carrots and parsnips or a side of creamy mashed potatoes.
- → Can I use pre-cooked lentils and quinoa?
For sure! Using ready-made or canned lentils and leftover quinoa will cut down your cooking time big time. Just make sure you rinse canned lentils really well to get rid of extra salt before mixing them into your stuffing.