Acorn Squash Filled with Shepherd's Pie

On a cool fall night I was served this dish from a local bistro, Stephanie’s on Newbury St. in Boston. I immediately was blown away by its inventive presentation of an age-old favorite- Shepherd’s Pie. Why they have not kept this on the menu I have no idea! For a dinner party the next weekend I recreated the dish because it was too pretty not to be revisited. Later I learned this is quite possibly one of the best make ahead dinner party foods or mid-week meals because you can cook all of it in stages. Roast the Acorn squashes and make the mashed potatoes ahead, then reheat once filled the meat mixture. Or for a dinner party, prepare and construct it all ahead of time and reheat before being seated.

One misfortune I have had in this dish is making a decent gravy. There are no real drippings from cooking the ground lamb, so stay tuned and perhaps one of these days I will figure out my workaround or if you have a suggestion by all means add it the comments section! It doesn't need the gravy, but it is always welcome!

Preparation:

1. Preheat oven to 350 degrees
2. Cut Acorn squashes in half, deseed and cut off the ends to create a flat surface for the squash to stand on.
3. Brush with olive oil and sprinkle salt and pepper on and in cavity.
4. Roast squash (and the ends and tops for about 20 minutes) in oven on baking sheet face up for 40-60 minutes.
5. Peel potatoes and cut in quarters. Add to boiling pot of water.
6. Boil potatoes for about 10 minutes until they can easily be poked with a fork.
7. Drain potatoes and add back to pot. Add butter and warmed milk slowly while mashing the potatoes. Add milk until desired consistency is achieved.
8. In a large sauté pan heat 3 Tbsp oil and add onion. Cook until softened, about 8 minutes.
9. Add ground lamb and brake up with a wooden spoon into smaller pieces. While meat is browning, after about five minutes, add carrots and corn. After another five minutes add peas and incorporate so the warm meat cooks the peas. Turn off heat and cover for another five minutes.
10. Fill the squash cavities with meat mixture up to the top and add a heaping dollop of mashed potatoes on top, spoon gravy over the top and add the discarded squash top or bottom as an added touch.