For residents of this island community, the summer season is a busy time. Many people arrive by boat and spend the summer months on the island. The island has only a few year-round residents and a limited number of businesses. The island has no dedicated business district and is only accessible by ferry from New Bedford, which runs once a day in the summer. During the shoulder seasons, a few small businesses are open.
The town of Cuttyhunk City is home to a one-room schoolhouse with a bell on top, a flagpole in front, and a 15-by-15-foot outdoor concrete basketball court. There is a church in the city, nominally Methodist, but the congregation is a mix of Christians, Jews, and Muslims. The town hall and the school are adjacent to each other.
The town has long been a popular tourist destination. In the 18th century, ferries connected New Bedford and Nantucket. The steamboat The Eagle carried 600 passengers across Nantucket Sound on May 15, 1818. Today, the M/V Whaling City Express serves as the base of ferry service to Cuttyhunk Island. The ferry service is a popular attraction in Cuttyhunk City, so make sure to plan an afternoon to visit!
There is an unnamed hill that rises above the city. This hill is situated west of downtown and is the highest point in the city. It rises to a height of more than 180 feet (55 meters) above sea level. There is a school in the town for children who have a disability. The school district also has a recreation center. There are numerous parks and trails for children. The city has a diverse population with many ethnic groups and religions.