A quiet fall weekend in Nantucket

I think Nantucket is always magical, but especially so outside of the peak summer season (which runs from July 4th through Labor Day). My favorite time of year here is the fall: The days are warm, the evenings are cool, and you can experience everything Nantucket has to offer—all while feeling like you have the island to yourself. Here's a good plan for a fall weekend on the island:

The Green is the best stop for organic, locally sourced sandwiches and snacks on the island. Grab a couple of veggie wraps and cookies to go, and you’re ready to hit the beach. The counter-service cafe is also centrally located—I like to stop here on my way to Surfside Beach.

I loved this restaurant for years before it closed for most of the pandemic—and I love it even more since it reopened in summer 2023 under new ownership. The menu offers seasonal, seafood-focused dishes that have interesting international influences. I had to order seconds of the lobster rangoon—it was that good. After dinner, ask about the basement speakeasy, where you can grab a nightcap.

Almost half of the island is preserved thanks to organizations like the Nantucket Land Bank, which maintains this gorgeous tract of land, a great spot for a (short, easy) hike. The trails traverse a wide-open stretch that culminates on a cliff overlooking Nantucket Sound. On clear days, you can spot the Great Point Lighthouse in the distance.

On an island with no shortage of stunning beaches, Madaket still feels remote, low-key, and beautiful. This time of year, something about the low-angle sunlight makes for extra-spectacular sunsets—I’ve shot some of my favorite Instagram posts here.

Named after a pioneering 19th-century female astronomer and naturalist, the Maria Mitchell Association operates two observatories as well as an aquarium to help visitors discover a more natural side of the island. In the off-season, it’s possible to book private Bird Walks, animal encounters at the aquarium, and astronomer-led "evenings under the stars" at the Loines Observatory.

Nantucket’s tiny downtown neighborhood offers surprisingly good shopping, considering you’re on an island 30 miles out to sea. Freedman’s is a great spot to pick up maritime-inspired home accessories and tchotchkes. The last time I was there, I picked up a beautiful mantle clock as a souvenir.

On a rainy day—and even on a sunny day, some would argue—the Whaling Museum is a fantastic activity for visitors of all ages. It’s operated by the Nantucket Historical Association, which keeps a mix of permanent displays and rotating exhibitions, so there's always something interesting to explore.