By car, Route 4 runs East-West through town and Route 7 runs North-South. Business Route 4 runs along the southern edge of the downtown.
Generally, it is a 4 hour drive from New York City, a 3 hour drive from Boston and a 4 hour drive from Montreal.
There is a Greyhound bus terminal at 102 West St, downtown.
The Amtrak station is at 25 Evelyn Place, also downtown, and is served by the Ethan Allen Express, a daily service to and from New York City.
Downtown Rutland is easily walkable, but to go anywhere else you'll either need a car or take public transit. There is a local bus service called The Bus. The Bus also runs to Killington for $2.
Rutland Falls is a nice waterfall just west of town on Otter Creek. It is crossed by a gargantuan railroad bridge and littered with huge slabs of authentic Vermont marble. It is accessible from Old Falls Rd, opposite the junction between Rt 3 and Business Rt 4.
The Vermont State Fair is held at the racetrack on South Main Street every September.
There is a wide range of eating options in the Rutland area.
Hemingway's Restaurant is an excellent four-star restaurant just east of the Killington base road turnoff on Rt 4. Try the chocolate cake.
Nearby Proctor, an old marble cutting town, is home to the Vermont Marble Exhibit. The town is pretty and also a little quirky because just about everything is made out of marble. Even the sidewalks.
Killington, the largest ski resort in the Northeast, is only a 20 minute drive to the east. They offer skiing in the winter and various recreational activities (mountain biking, hiking) in the other months of the year.