Tessa Cressman’s Winter Guide to Nantucket

Born-and-raised islander Tessa Cressman, the co-founder of The Green Market, has created a space celebrating everything that makes Nantucket unique. But what does she do in the off-season? Read on for her Nantucket winter travel tips.

Get into nature

Over half of the island is open land, and there are so many beautiful walking trails. My favorite is through Squam Swamp, toward the eastern end of the island—it’s so hidden. And I love driving out to Sankaty Light to watch the ocean. The waves can be so wild in the winter, and looking out from those cliffs on a windy day takes you back in time.

Stroll downtown

The off-season is when we all catch up on reading, and I love taking my boys to the Nantucket Atheneum’s childrens’ library. I also treat myself to a few books from BookWorks or Mitchell’s Book Corner. And I always stop for a London Fog from the Corner Table.

For an evening out, the Gaslight is the spot to see all the best local bands, and it’s got such a cozy dinner menu. I love the miso cod rice, and their burger is delicious and not giant—you don’t need a whale-shark mouth to eat it!

Tap into the community

After the nuttiness of the high season—I love taking more time to chat with people I haven’t seen. The winter is when the locals get a chance to reconnect. If you’re visiting during the calmer months, it’s a good time to strike up a conversation and get a better feel for island life. 

November through March is scalloping season and, if you’re a fan of Nantucket bay scallops, join the Nantucket Shellfish Association. They’re a small group doing great things to clean up the water and protect the island’s harbors, and membership is a fun way to stay connected.

The Green Market is a small marketplace environment with food products ranging from organic produce and baked goods to grab-and-go meals. Adorned with fresh flowers and plants, New England antiques, and exceptional household items, the Green Market carries a vast selection of clean beauty and skincare products from renowned brands such as OSEA and Tammy Fender. 

When booking your stay at Greydon House, add a Green Market “mini-bar” basket when you book directly on our website.