Many came to enjoy the fresh air and to escape the oppressive heat of summer back home in Pennsylvania, Maryland, Florida, Missouri or the Carolinas. For others it was far enough from home to provide a real vacation - to be free from social and work expectations, as many visitors had high-pressure careers back home. In Chester they could kick back and really relax. Hunting and great fishing continued to be a draw. Fishing boats could be rented to take families out to one of the numerous islands on the Mahone Bay for swimming, walks in the forest, picnics, clam digging, or enjoying fresh lobster cooked over a beach fire.

"...Chester is not what one would call a "smart" place, heaven forbid! It has character and grace and beauty and charm. Having these qualities, it could not be pretentious. As yet it is unspoiled... I dread writing too enthusiastically of it, lest hoards infest it, and make it only one more "summer resort", instead of the delightfully quiet spot it is to-day. ...."- Charles Hanson Towne from "Ambling Through Acadia", 1923 p.242

There was little pretence in Chester and the visitors liked that. The men especially liked to drop social conventions, "scruff around on a boat", and even drink and swear with little fear of judgment. The women also enjoyed a little more freedom than they might have at home. They often spent longer periods in Chester than their husbands and fathers, and so a strong women's social network developed. Visitors who employed locals and treated them well were repaid with loyalty and discretion. Anyone who looked down on the locals didn't get far. Discretion was highly valued.

These summer residents invited additional family members and friends, bringing even more visitors to Chester. By the 1880s this network became an essential part of the local economy. Work at the inns, hotels and boarding houses quickly became a substantial part of the income of local men and women, as did providing food, guides for hunting and fishing, and boat excursions.