3 Ways to Fall in Love with Nantucket in September

It doesn’t get much more picturesque than fall in Nantucket. From the crisp leaves on the cobblestone streets to the suddenly dormant beaches still yearning to be visited. September through November is said to be the local’s favorite season because foot traffic is light, and the weather is bright. Discover everything you need to know about visiting Nantucket in September.

Learn more about Nantucket when you access our complimentary Vacation Guide. Our guide offers hand-picked recommendations on where to eat and what to do during your stay.

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Everything You Need to Know About Nantucket in September

Fall is secretly the best time of year to visit the Grey Lady. As we head towards the winter months, the downtown streets began to get sparse, and the once crowded beaches start to thin. Explore the best of the island when you visit Nantucket in September!

  • Visit the Beach

Chances are you’ve already made plans to visit one Nantucket’s sandy shores, but did you know that you’re actually visiting at a prime time? Make your way to Madaket or Siaconset in early September, and you may even get to enjoy the salty waters before the cool air hits. Visit at the end of September and enjoy the stillness of a nearly private beach as you stroll along the coastline. There’s nothing quite like Nantucket beaches in the fall.

  • Experience Cranberry Season

Cranberry season is truly special in Nantucket. Take a step back in time when you attend the Annual Cranberry Festival. Throw on some waders and hop in the bog for a firsthand try at an authentic wet harvest. Or bring the kids and enjoy sack races, face painting, Barnaby Bears, and antique tractor shows. The event features live music and delicious food tents. It is one September event that you won’t want to miss!

  • Nantucket Island Fair

Located at Tom Nevers Fairgrounds, the Nantucket Island Fair is wholesome fun for all ages. The fair offers traditional games, a watermelon eating contest, scarecrow building, a barnyard tent, live music, a farmers market, and so much more. The time-honored tradition is taking a break for the 2020 season but will be back in action on September 18 and 19, 2021.

Cozy Up at the Downtown Anchor Inn

Stay in the heart of Nantucket when you reserve your spot at the Anchor Inn. Whether you’re looking to experience authentic Nantucket from one of our charming rooms or need some space to spread out in our private Bungalow, our beautiful accommodations do not disappoint. The Bungalow is Nantucket’s newest downtown vacation rental and features two bedrooms and three baths. It’s the perfect option for larger groups!

Discover more of Nantucket and all of the best things to do during your stay. Whether you’re climbing the tower of the First Congregational Church and biking through some of the best routes on the island, you will experience the island’s charm from right here at the Anchor Inn. We can’t wait to welcome you to our island in the sea!

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