In 1759, the site that is currently known as Rutland was built by the British as an outpost on the military road crossing the state of Vermont. Rutland connected forts on Lake Champlain with the Connecticut River valley, and its location was centered around its farmland and topography. Chartered in 1761, the settlement was likely named for Rutland, Massachusetts, the home of one of the early settlers. However, another theory holds that the town was named after the influential Duke of Rutland. Rutland is the home of Vermont's oldest newspaper, the Rutland Daily Herald, which has been published continuously since 1794. In the early 19th century, small high-quality marble deposits were discovered in Rutland and a few years later in the 1830s, a large deposit of nearly solid marble was found in what is now West Rutland. After Rutland was incorporated as a village in 1847, railroad construction and marble quarrying stimulated growth. In fact, the famous quarries of Carrara in Tuscany, Italy, became largely unworkable because of their extreme depth and Rutland quickly became one of the leading producers of marble in the world. This fueled so much growth and investment that by the 1880s, Rutland became Vermont's largest municipality. In 1886, the surrounding marble-producing communities of Proctor, Rutland town and West Rutland town, withdrew and since then the City of Rutland, which incorporated in 1892, has been second in size to Burlington. However, the closing of many marble quarries in the 1980s and 1990s led to significant job loss in the area.

There are plenty of things to see and do in Rutland considering its small size. The lovingly restored historic Merchant's Row dates back to the mid-19th century, with many interesting shops, restaurants and a lot of banks and municipal buildings.

For those keen to buy local, organic artisanal foods, there’s also a summer Farmers' Market in downtown's Depot Park and a winter Farmers' Market in the Vermont Farmers Food Center.
The bandstand in the Main Street Park, opposite the Chaffee Art Center, features a vibrant and well-attended Summer Concert Series.

Fully restored in 2000 after several years of abandonment, the Paramount Theater is one of the most beautiful buildings in New England. With 838 seats, the theater offers an outstanding approach to live entertainment and plays a significant and valuable role in the community since assuming its role as an arts, cultural and educational center.

The 275-acre Pine Hill Park offers access to mountain biking, hiking and many other outdoor pursuits. At the park's entrance is the Flip Side Skatepark, which is municipally operated in an open-sided closed roof arena at the Giorgetti Athletic Complex.

Founded in 1937 with 57 runs is the nearby Pico Mountain Ski Area – one of Vermont’s first commercial ski and snowboard resorts. It is now operated by POWDR, one of North America’s largest ski operators. Pico Mountain has newly upgraded snow making equipment on 75 percent of its runs and the area also receives significant natural snowfall.

Deer Leap Trail is an easy one-hour hike and perfect for a clear, sunny day with its amazing view at the top as a reward.

As an area of outstanding natural beauty, Green Mountain National Forest was established in 1932 to fight uncontrolled overlogging, fire and flooding. The forest contains three nationally designated trails, three alpine ski areas, seven Nordic ski areas and approximately 900 miles of multiple-use trails for biking, cross country skiing, hiking, horseback riding and snowmobiling. If you are lucky enough to spot one, you may see a variety of wildlife in the forest, including beaver, black bear, coyote, moose, white-tailed deer, wild turkey and ruffed grouse.

Avid golfers will enjoy the greens at the city’s three local golf courses – The Green Mountain National Golf Course, the Neshobe Golf Club and the Okemo Valley Golf Club.