We asked our team at LRE to share their favorite fall spots on the island, places to walk, sip coffee, watch sunsets, or simply take in the beauty of the season. The responses remind us that while we may all love Nantucket for its peaceful charm, each of us finds that tranquility in our own unique way.
Morning Walks, Hidden Trails, and Peaceful Routines
For Kiri and Shawn, fall mornings begin with quiet walks through Codfish Park alongside their dogs. There’s something special about that early light and the calm hush of ‘Sconset before the day begins. It's pure Nantucket serenity and if you know, you know. Bruce prefers exploring the island on two wheels, pedaling out to the Perkins trails hidden in the Middle Moors. He says, “if you can find them, you’ll feel like you’re biking through the hills of Vermont.” It’s the kind of hidden gem that makes Nantucket so endlessly surprising. Meanwhile, Maya enjoys peaceful strolls around Miacomet Pond, where she takes in the beauty of the water and the homes surrounding the trails. It’s a favorite local spot to unwind, reflect, and appreciate how the colors of fall transform the island. Jodi enjoys an epic fall sunset at Great Point with her husband, often with their dog, Rex, by their side and it's such a bonus in the off-season that dogs are once again allowed in this part of the island! And for Jeff, it’s all about Tuppancy Links, “No matter how many times you walk that trail, the scenery never gets old,” he says.
Local Eats and Cozy Fall Bites
Of course, no island day is complete without good food. Jeff, has you covered with a few must-try favorites. If you haven’t stopped by 167 Raw’s food truck, he recommends the fish sandwich or the tuna poke with guacamole. And the Smashburger at Straight Wharf Fish is delicious (just don’t forget extra napkins!). Shellie enjoys crisp fall bike rides out to Madaket, where the skies turn into a painter’s masterpiece at sunset. Afterward, she loves to warm up with soup and grilled cheese from Born & Bread. She and Dan stroll down an almost-empty Main Street, soaking in the beauty of a town that feels straight out of a storybook. “It’s like living in a real-life fairytale,” she says and we couldn’t agree more. Liza looks forward to the off-season dining scene, when she can walk into her favorite restaurant without a reservation. “That’s when the magic happens,” she says. There’s something special about that relaxed, familiar rhythm that makes every meal feel more meaningful. Peter can often be found grabbing breakfast at Pip & Anchor, a local favorite known for its market-fresh offerings. His go-to? The breakfast tacos with chorizo, yes they offer a veggie version and he insists you won’t regret trying the sourdough bread too! Drew keeps the energy going with a coffee in hand, often cheering on Whaler sports games or strolling through town with a stop at The Verdant Maiden. And if you’ve never caught a Whalers vs. Martha’s Vineyard game, it’s an island tradition worth experiencing at least once!
Finding the Beauty in the Grey Lady
Each of us on the LRE team finds beauty in the island’s quieter months, when the beaches are empty, the trails are peaceful, and the sunsets seem to linger just a little longer. Fall on Nantucket is a time to reconnect with what makes the island so special: its simplicity, its charm, and its ever-changing natural beauty.
Whether you’re a longtime islander or visiting for the first time, we hope you’ll discover your own favorite fall moments here on the Grey Lady. And when you’re ready to make Nantucket part of your story whether it’s for a weekend, a season, or a lifetime, we’d love to help you find your place in this beautiful community.