Everything You Need To Know About Exploring Nantucket In October

Fall is one of the best times to plan a visit to Nantucket. The crowds have gone, the beaches are flawless, and the weather is perfectly crisp. Locals love it because you can walk right into some of the best restaurants on the island and enjoy a side of The Grey Lady that only a few get to see. We have everything you need to know about exploring Nantucket in October this year!

Discover even more of our quaint island when you access our exclusive Vacation Guide. Our complimentary guide provides hand-picked recommendations on the best restaurants, shopping, and things to do. Get yours today!

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Discover the Charm of Nantucket in October

Locals will argue that Nantucket’s sweet spot is somewhere between the first leaves hitting the cobblestone and the seaside cottages’ first dusting. Watch as this tiny island in the Atlantic transforms into a Norman Rockwell painting when you visit Nantucket in October. 


  • Nantucket Wine and Food FestivalLola 41

Lola 41 is located just outside of Nantucket Harbor on South Beach Street. They offer everything from sushi to burgers alongside artisan cocktails in a contemporary, waterfront setting. It’s a hop, skip, and a jump outside of the cobblestone streets, making it a favorite for Nantucket locals.

  • The Nautilus

The Nautilus is one of those Downtown Nantucket where you, typically, have to fight for a reservation. It’s the perfect place to visit in the fall because you can walk right in and enjoy the same five-star service and cuisine that the summertime provides. You can expect fresh seafood creations, farm-to-table produce, delicious cocktails, and the friendliest service. 


  • Nantucket bike toursSankaty Head Lighthouse

Get outside of the city and take a trip to ‘Sconset’s Sankaty Head Lighthouse. The cliff-side light was built in 1850 and still protects sailors from the island’s rocky edges today. While you’re there, spend some time walking through the cottage-lined streets, exploring Sconset Bluff Walk, and dining at some of the local restaurants.

  • Take a Bike Ride

Swing by Young’s Bike Shop and rent your ride for the day. A Nantucket bike tour is one of the best ways to explore the island, and October temperatures allow for the perfect setting. Adventure is endless in Nantucket!


  • Periwinkle Inn - Exterior - Backyard with shaded seating areasThe Periwinkle Inn

Plan your stay at our cozy Nantucket inn by the harbor. Our downtown bed and breakfast offers a traditional view of the island with neighborly amenities. Many of our guest rooms feature waterfront views, and all of them are uniquely themed from Herman Melville’s Moby Dick.

Book the Pequod Room and revel in a hand-tied fishnet canopy over your cherry wood, queen-size bed. Enjoy views of the cobblestone and gardens below, plush Turkish towels, Egyptian cotton linens, and Malin + Goetz bath products. We can’t wait to welcome you to Nantucket this fall!    

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This small-island town charm will provide the perfect backdrop for a relaxing, romantic escape!