The Vermont Teddy Bear Company is one of the largest producers of teddy bears and the largest seller of teddy bears by mail order and Internet. The company handcrafts each of its teddy bears and produces almost 500,000 teddy bears each year. The company was formerly traded on the NASDAQ stock exchange under the ticker symbol BEAR, but was taken private by The Mustang Group, a Boston-based private equity firm, on September 30, 2005, partially to avoid the reporting requirements of the Sarbanes-Oxley Act.

The company was founded in 1981 by John Sortino, who sold handcrafted teddy bears in an open-air market in Burlington, Vermont. Sortino happened upon the idea of packaging and selling bears through the mail when a tourist visiting Burlington wanted a bear mailed to her home. The concept was called the "Bear-Gram", which features the customized teddy bear placed in a box (complete with an "air hole") and stuffed with other goodies.

By 1995, the company moved into its new headquarters in Vermont's Champlain Valley. The company currently has two factories: one in Shelburne and one in Newport. The Shelburne factory is an especially popular tourist destination, and also serves as a concert site for the annual Vermont Mozart Festival, offering a venue for family-oriented events. The company also maintains two retail locations in Vermont - Shelburne and on the main road between Waterbury and Stowe.

VTB acquired Calyx & Corolla, an upscale flower company headquartered in Vero Beach, Florida in 2003. Ironically, one of Vermont Teddy Bear's marketing slogans claims that sending a teddy bear is "a creative alternative to sending flowers". In 2005, the company launched a new sister company, Gift Bag Boutique, which offers handbags and purses along with many make-up accessories. Along with PajamaGram, which sells gift pajamas, and TastyGram, which offers gourmet food gifts, the creation of this sister company brings the total number of companies under the Vermont Teddy Bear umbrella to five.