• Why I’d Go: Historic New England charm with a fresh point of view. Dating back to 1883, The Asticou has been beautifully restored into the kind of understated luxury escape that feels completely at home on Mount Desert Island.
• The Setting: Twenty-five acres overlooking Northeast Harbor with Acadia National Park just beyond your doorstep. Think crisp coastal air, brilliant fall color, harbor views and mornings that practically require a great sweater.
• What to Do: Acadia National Park is the main event. Spend the day hiking, exploring the rocky coastline and taking in the foliage. This is exactly why we packed the chic outdoor layers.
• Dinner: Keep it easy and stay on property at Dahlia’s, where seasonal coastal Maine ingredients set the tone for a cozy dinner after a day outside.
• After Dinner: Move to the wonderfully moody Moss Bar for a nightcap—the perfect ending to a crisp Maine fall day.

• Why I’d Go: A gorgeous countryside escape that feels worlds away from the city. Pendry Natirar is set on a sprawling Somerset County estate, with a beautifully restored 1912 Tudor-style mansion at its heart. Historic on the outside, incredibly polished and current everywhere else.
• The Setting: Rolling countryside, beautiful grounds and that quintessential fall-on-an-estate feeling. It’s the kind of place where you can spend the entire weekend on property and never feel like you’re missing anything.
• What to Do: Take advantage of the estate. Hike, bike, try archery or book a hands-on experience at The Cooking School. I love that this weekend can be as active—or as leisurely—as you want it to be.
• The Spa: This one deserves its own moment. Spa Pendry has eucalyptus steam rooms, cedar saunas, a halotherapy salt room, an indoor tranquility plunge pool and an outdoor terrace overlooking the countryside. Translation: book the appointment.
• Dinner: Make a reservation at Ninety Acres, where the menu is inspired by the estate and surrounding farms. This is the kind of destination dinner that makes staying on property feel especially good.

• Why I’d Go: Mohonk is an icon for a reason. This historic Victorian resort sits above Lake Mohonk in the Hudson Valley, surrounded by thousands of acres of protected forest. And while it’s beautiful year-round, fall feels like the moment to experience it.
• The Setting: Think dramatic cliffs, a mountain lake, miles of wooded trails and incredible fall foliage. This is absolutely a check-in, park-the-car-and-don’t-think-about-leaving-until-Sunday kind of weekend.
• What to Do: Hike. Fall is prime time to explore Mohonk’s trails, and the resort offers guided hikes through the property. For something with a little more adrenaline, try the famous Lemon Squeeze rock scramble, mountain biking or the seasonal Via Ferrata experience.
• The Spa: Adventure first, robe second. The Spa at Mohonk Mountain House has an outdoor heated mineral pool, eucalyptus steam room, sauna and a gorgeous solarium with a stone fireplace. There are also seasonal outdoor wellness experiences overlooking the lake and surrounding cliffs.
• Dinner: Chef’s Table at Mohonk Mountain House — For a true splurge, stay right on property for Mohonk’s intimate Chef’s Table experience. Offered Friday and Saturday nights, this special evening takes you behind the scenes in the kitchen for a 10-course tasting menu with thoughtfully paired wines. It’s the perfect way to end a day in the mountains and absolutely worth planning ahead for—reservations are limited, so book early.

• Why I’d Go: For the quintessential Vermont fall weekend. Woodstock in October almost feels too perfect to be real—historic buildings, covered bridges, brilliant foliage, farms and charming little shops, with the Woodstock Inn sitting right on the Village Green.
• What to Do: Book the falconry experience. Yes, falconry—and I cannot think of a better excuse for a fabulous countryside outfit. You can also spend the day fly fishing, hiking or biking before wandering through Woodstock Village.
• The Spa: After a day outside, make time for the Inn’s Forbes Four-Star-rated spa, a 10,000-square-foot retreat featuring Vermont-inspired seasonal treatments. Fall adventure followed by a robe is exactly the itinerary we’re after.
• Dinner — Red Barn Dinner Series at Kelly Way Gardens: If your stay lines up with a 2026 Red Barn Dinner, make the reservation. This intimate farm-to-table experience pairs seasonal Vermont ingredients—many grown right in Kelly Way Gardens—with accompanying wines. A quintessential Vermont fall evening worth planning around.

A Little Note: I put this guide together using my own research, with a little help from AI to dig deeper and find some of the best spots and experiences to include. Consider it your starting point for planning a fabulous trip—and always double-check reservations, hours and availability before you go!