The best time to visit Cuttyhunk is during the summer months, from late June through early September, when the weather is warmest and the island is fully operational.For all visitors, especially families and couples, this period offers the most pleasant conditions for enjoying outdoor activities. The average daily temperatures range from the mid-70s to low 80s Fahrenheit, making it ideal for swimming, fishing, and exploring the island's natural beauty. All local businesses, including the general store, restaurants, and ferry services, operate on their full summer schedules, ensuring you have access to all amenities and activities.If you prefer a quieter experience with fewer crowds, the shoulder seasons of late May to early June or mid-September to early October are also good options. The weather is still generally mild, though cooler, and you can enjoy the island's tranquility before or after the peak tourist rush.