I spent the first weekend of October on Nantucket and stayed at The Brant, a boutique property that was the perfect home base. Tucked just outside of town, it’s close enough to walk in for anything but far enough to feel peaceful and private. The staff couldn’t have been more accommodating, offering the best recommendations and making every morning feel special. One of my favorite parts of the stay was sitting out on the front porch with my coffee (the coffee was so good I brought a few bags home), watching the quiet street come to life.

Nantucket in early October is now my favorite time to visit. During the days, we loved walking to the beach from The Brant, biking around the island (Nantucket is so bike-friendly), and exploring all of the boutiques. In the evenings, we enjoyed cozy dinners and drinks in town.

My Favorite Spots

• The Nantucket Tap Room — Classic New England atmosphere inside the Jared Coffin House. We sat outside for a view of my favorite street on the island. The burgers are the best.
• Cisco Brewery — Fun spot for a casual afternoon with food trucks, drinks, and live music. Don’t miss the Nantucket Lobster Trap truck.
• Sandbar — A casual beach bar just a short walk from The Brant — perfect for a relaxed lunch or drink by the water.
• Sconset — The Bluff Walk views made the long bike ride out here worth it. We stopped at Claudette’s afterward for sandwiches.
• Galley Beach — Go early to catch the sunset. They have a beautiful lounge right on the sand for cocktails before dinner.
• Juice Bar — Ice cream here is a must, even in October.