There’s something special about Nantucket in the fall. The island slows down after the summer rush, and what’s left feels calm and almost cinematic. The air turns crisp, perfect for sweaters and jeans in that classic Nantucket style. It feels like stepping into a movie scene, where every corner has a story and the pace matches the season. And, on my latest trip, filming had commenced for Nantucket’s famed author, Elin Hilderbrand’s upcoming series ‘The Five-Star Weekend’ (helmed by Jennifer Garner), making it all the more star-studded.
Stay
We stayed at The White Elephant, which felt like the perfect fall haven and escape. The hotel sits right on the harbor near Children’s Beach, where you can watch fishermen casting their lines as the sun rises. Each afternoon, they host a port and cheese tasting in the lobby, which is the kind of thoughtful touch that makes you slow down and enjoy where you are. The property has a beautiful restaurant overlooking the water and plenty of space to walk or sit and take in the view. If you’re traveling with little ones, there’s a great playground nearby, and the staff couldn’t be more family-friendly. It’s also walkable to town and has a convenient shuttle to the ferry. We checked out the pool and it’s a lovely outdoor oasis, open through early September.
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Another wonderful option is The Nantucket Hotel. It’s also close to town and has a cozy, classic feel. They offer daily shuttles to Cisco Brewers and around the island, which makes exploring easy. The children’s club is amazing, the spa is relaxing, and the gym is one of the best I’ve seen at a hotel on the island.
Eat
There’s no shortage of great food in Nantucket, and fall feels like the best time to enjoy it. Cru is a famed favorite for its harbor views and upscale atmosphere. It’s lively at night and perfect for oysters and champagne. Or, The Whale and The Proprietors Bar & Table are both fantastic dinner options in town with warm service and seasonal menus. For breakfast or lunch, Lemon Press is a beautiful, airy spot with fresh juices, matcha, and a relaxed grab-and-go option if that’s more your vibe. For a good cup of coffee, try Handlebar Café or Espresso to Go.
If you’re heading to the beach or need sandwiches for a picnic, Provisions and Something Natural are both island staples. And when it comes to ice cream, nothing beats Juice Bar. It’s a must. When the day winds down and it’s time for a drink, Sister Ship has a cozy garden courtyard with a great atmosphere. The Club Car, set in an old train car, is charming and fun for cocktails. Gaslight is always buzzing with live music and energy. And of course, no trip is complete without an afternoon at Cisco Brewers. It’s one of the happiest places on the island — an open-air space filled with people, live music, fresh oysters, and local beer. It captures everything that’s special about Nantucket in one place.
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Explore
Fall is a beautiful time to explore Nantucket’s natural scenery. The Bluff Walk in Sconset is one of my favorite things to do. Think: A quiet path along the edge of the ocean with sweeping views and charming cottages along the way. In town, it’s easy to spend hours wandering through the historic streets, taking in the weathered shingle houses and blooming hydrangeas that linger into the season. The island feels more peaceful in the fall, with enough life to keep it interesting but enough quiet to feel like you’ve truly escaped.
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