Those in the know are wise to the fact that New England is often at its best when September and October roll around. Nantucket is especially an attractive destination this time of year. In fact, many locals relish the shoulder season, when the water is at its warmest, the large number of summer visitors has vanished, the traffic disappears and reservations aren’t needed at their favorite restaurants. For those who have limited free time right now, even spending a weekend on the island in autumn can be magical.
Taking a ferry is always a lovely transition from mainland life to island time, but if every hour is of the essence, Cape Air offers several flights a day to Nantucket from Boston and New York. However you arrive, we recommend basing yourself at one of the Nantucket Island Resorts properties, a collection of hotels (which includes Forbes Travel Guide Four-Stars The White Elephant and White Elephant Village) with various styles of accommodations that range from lofts in the heart of town to a small, romantic treasure on the far side of the island.
If you want to be in the middle of everything, The Cottages & Lofts at the Boat Basin is a great base. Choose from studio lofts, three-bedroom cottages and units in between, all within walking distance of the harbor, restaurants and shops. (Complimentary bicycles are available for times when your feet start aching.) For those who want to get away from it all, though, the Four-Star The Wauwinet is an idyllic getaway, located just nine miles from the center of town. Built in 1876 by ship captains, the resort offers two private beaches along Nantucket Bay and the Atlantic Ocean. In other words, once you dock here, you’re assured a most peaceful stay.
Wherever you rest your head, exploring the island with just a map and a bike is a great activity — though there are plenty of guided tours as wells. One thing you’ll notice around town is that just about all of Nantucket has gotten in on the excitement surrounding the December movie release for In the Heart of the Sea, a Ron Howard-directed adaptation of Nathaniel Philbrick’s best-selling book chronicling the tragedy of the Nantucket whaleship Essex in 1820. The Nantucket Historical Association has a 90-minute In the Heart of the Sea walking tour going through late October, which takes you to locations related to the Essex. There’s also a major exhibition, “Stove by a Whale: 20 Men, Three Boats, 96 Days,” on display at the Whaling Museum through November 2016. And when you’ve had enough of the rugged seas, don’t miss the Nantucket Lightship Museum, where you can learn about the history of the island’s iconic handmade baskets.
Options for wining and dining on the island are plenty. Even if you aren’t able to stay at The Wauwinet, book a table at its restaurant, Four-Star Topper’s, where the best thing you can do is put yourself in the capable hands of chef Kyle Zachary for the evening. The three-course prix-fixe menu is the way to go, where dishes might include seaweed butter-poached lobster or Grand Banks halibut confit à la minute. The locally harvested Retsyo oysters, served on the half shell, are cultivated a mere 300 yards from The Wauwinet and are a must.
Should you need any more excuses to visit the area, two fall festivals just might be what you’re looking for. Nantucket Restaurant Week (September 28 to October 4) will see more than two dozen restaurants offering prix fixe meals at delightful prices. The 13th annual Cranberry Festival (October 10) is a can’t-miss celebration where you watch the fruit being harvested at Milestone Bog, learn about the history of cranberry farming on Nantucket and enjoy food, music and other activities.