Preheat the oven to 400 F.
Place the beef roast in the center of a medium sized roasting pan. Toss the carrots, parsnips, sweet potatoes, and squash around the beef roast. Season with Italian seasoning, then drizzle olive oil and balsamic vinegar over the top.
Cover the roasting pan and place in the preheated oven. Cook for about two hours, depending on the size of the roast.
Insert a meat thermometer and cook until 140 F for medium to 165 F for well done.
If you prefer a juicier, but less crusted roast, cook it at 325 F for about three hours, or until the meat thermometer reads 145 F, for medium-well.
Serve beef roast with winter vegetables as is, or with simple side salad.