There is a great ski shop in downtown Kingfield. It's called the Sugarloaf Sports Outlet. I think they do rent ski's there. Even if they don't check it out for some good deals on most equipment and clotheing.
Dining on mountain.....Bullwinkles. At the base for drinks and appetizers, Widowmaker. Great sandwiches at the base, D'Ellies. Good food at the base, Ghepetto's. Good food close to the mountain, Hugs and Tufulio's. Good food and drink in Kingfield, Longfellows. Good breakfast in Kingfield, Log Cabin. Lots of choices and most all of it is good.
Mountain info.....2 ways to start your day. 1) Superquad to access lots of good warm up runs, including Tote Road (blue) or Kings Landing (blue) or Mid Narrow Gauge (black) or Hayburner (black). All groomed to perfection. The second way to start your day would be to hit the Whiffletree Quad. Lots of good green warm up runs from this lift. Or, take Whiffletree up and exit left onto Tohaul and ski down to the King Pine quad to access some tougher blacks and tougher blues, Haulback and Ramdown respectively.
Eventually you should do laps on the Spillway chair. This chair accesses some great black, double black terrain and also lots of blue terrain. When the desire is for a challenge, exit Sillway Chair left. Exit right for some great green and blue runs.
To hit the Spillway chair without going all the way to the bottom, learn 2 cross cut trails....Peavey X-Cut and Lombard X-Cut. These 2 trails give you access to the Spillway chair that services the face of the mountain, some really fantastic skiing right there!!
Also, remember the Timberline chair. This chair gives you access to the snowfields and 2 trails that must be skied....Tote Road and Timberline. Blue and Green trails. On the days that this chair runs Sugarloaf is at it's best. This chair opens up the world to any eastern skier and the smile on your face will hurt by the end of the day. 2,850' of vertical from this chair with views that are out of this world.
As for entertainment.....there's some. But I strongly suggest that you eat, sleep, ski. After all, we're talking da 'Loaf.!!!!
May you have great weather and enjoy your trip.