The Greater New Haven area includes not only the relatively metropolitan New Haven, but also more rural areas. Cheshire, which has a population of 26,000 was settled in 1694 and is approximately 14 miles north of New Haven at the intersection of three interstate highways. For most of the last 200 years, Cheshire was predominantly a rural farming community and still has thousands of acres of open space and an active agricultural industry. Cheshire currently has several high technology industrial parks hidden amongst a series of parks and recreational areas, and adjacent to Connecticut's ski areas.

To the south of Cheshire, New Haven combines the livability of a small town with the sophistication and cultural diversity of a big city. Located in southern Connecticut, with a harbor on Long Island Sound, New Haven has a downtown small enough to walk from end to end on foot. However, New Haven offers many of the amenities and resources of a large metropolis, including a variety of fine restaurants that rival the selection available in many larger cities. The character of New Haven is distinguished by the presence of Yale University, contributing some of the quaint characteristics of a campus town as well as the world class scientific and cultural resources of a pre-eminent center of academic scholarship. Greater New Haven to the East provides attractive shoreline communities, to the West extensions of Fairfield County, and to the North rural communities.

Greater New Haven boasts three nationally regarded off-Broadway theaters: The Shubert Theater, The Long Wharf Theater and The Yale Repertory Theater. In addition to this wealth of theatrical venues, New Haven regularly attracts a broad variety of musical talent, including rock and roll, pop and classical performers. These performers grace the stages of Toad's Place, The Palace Theater, Oakdale Theater and a number of other sites throughout the Greater New Haven area. The Summer International Arts Festival attracts musicians and artists from around the world. The New Haven Symphony Orchestra performs at Woolsey Hall on the Yale campus and has attracted a number of notable talents.

Water sports, including fishing and sailing are as close as the Long Island Sound, while the nearby Connecticut countryside offers hiking, camping, skiing, and many other outdoor activities. Beyond the immediate area, the slopes of Vermont and New Hampshire, the beaches of Cape Cod, the mansions in Newport, the lights of New York City, and the Boston Pops are all within easy reach. By car or train, New York City is approximately one and one-half hours and Boston is approximately two hours from Greater New Haven. The beauty of the surrounding countryside together with the proximity of other major cities and access to the recreational resources of the northeast makes this area a wonderful place to live, work, and raise a family.