Mount Wachusett is named after a Native American term meaning "near the mountain" or "mountain place". The mountain is a popular hiking and skiing area. Wachusett Mountain State Reservation offers 17 miles of hiking and walking trails, including 3.9 miles of the Midstate Trail. A road to the top is open from Spring to Fall. On clear days you can get views of Mount Monadnock to the north, and Boston to the east. This is a fun little get away from Boston, it is about an hours drive.
Take route 2 heading West to exit 25. Turn right on route 140 heading South. Go for about 2 miles and turn right on Mile Hill road. (follow the signs for Wachusett Ski Area.) Take a right at the Wachusett Ski Area Sign, and park in the parking lot.
Take Route 290 heading East to exit 19 (190 North). Take Exit 5 off of 190 North which puts you onto 140 North. Follow that road for about 9 miles. Take a left turn onto Mile Hill road. Then take a right into the Wachusett Ski Area parking lot, and park there.
No red tape that I know of.
You can hike Mount Wachusett all year long. The average summer temperature is about 80 degrees Fahrenheit, so take plenty of water. The average winter temperature is about 20 degrees Fahrenheit, so wear appropriate clothing. There is also about 100 inches of snow during the winter, so be sure to bring the snowshoes. For current weather conditions check out www.onthesnow.com