Whether it was just a haunting feeling about where we were hiking, or perhaps an unnerving vibe that kept us on edge looking over our shoulders, these dog friendly places are not your average New England dog hikes. To learn more about these spooky adventures, please click on the highlighted name, or visit our Dog Friendly Places page. Please remember these trails are open dawn to dusk, and are closed at night, and always be respectful of these historic sites, because you never know who or what may be watching you.
Madame Sherri Forest: Located in Chesterfield, New Hampshire, the ruins of Madame Sherri’s castle include a mysterious stairway to nowhere. It is said if you’re quiet, you can still hear the haunting sounds from the parties that took place here during the Roaring Twenties.
Difficulty: Easy if you go straight to the ruins. Moderate to difficult if you explore the Ann Stokes Trail.
Dogs are allowed on-leash.
Admission: Free
Beech Valley Trail: Most people visit Acadia National Park for it’s mountaintop views and scenic coastline. However, if you’re looking for a different perspective, visit the Beech Valley Trail in Southwest Harbor, Maine. When hiking this boulder strewn trail, surrounded by sheer cliffs towering overhead on one side, and steep drop-offs to the forested valley below on the other, we couldn’t help but find ourselves looking for mythical creatures and dinosaurs around every turn.
Difficulty: Easy to moderate
Dogs are allowed on-leash.
Admission: Acadia National Park passes are needed to access Beech Mountain Valley Trail from May through October, but are not available for sale at the parking area. To purchase a park pass please visit the National Park Service.
Sears Island: If you ever wanted to feel like you’re hiking in a post-apocalyptic world, visit Sears Island in Searsport, Maine. The main trail is an eerily abandoned paved road with grass growing through the cracks surrounded by dense forest. This gave us the unnerving feeling that zombies were lurking. Explore the many smaller and overgrown trails off of this, and you will find the remains of house foundations, old wells, moss covered stone walls, and heirloom apple trees from the island’s lost farming community.
Difficulty: Easy to moderate
Dogs are allowed under owner’s control.
Admission: Free
Satan’s Kingdom: You won’t find fire and brimstone at Satan’s Kingdom in Northfield, Massachusetts. What you will find is an extensive network of unmarked trails reminding visitors of what the early settlers in this area feared most – the unknown. However, as you wind your way through the dense forest, open meadows, and wetlands on unmarked trails, you’ll soon realize there is nothing to be afraid of in these woods.
Difficulty: Difficult. Please use extreme caution if you visit. There is an extensive network of unmarked trails here, making it easy to get lost, and cell service is poor at best, if available at all.
Dogs are allowed under owner’s control. We recommend both you and your dogs always wear blaze orange because in addition to hunting, target practice is permitted year round with written permission from the Massachusetts Division of Fisheries and Wildlife.
Admission: Free
Ravenswood Park: Named for the castle in Sir Walter Scott’s tragic love story, “The Bride of Lammermoor,” at this 600 acres property in Gloucester, Massachusetts, you can search for the remnants of Colonial cellar holes, pay your respects at the memorial for a hermit that once called these woods home, or ponder what could be hiding behind the enormous boulders that are strewn about this park.
Difficulty: Easy to moderate
Dogs are allowed off-leash with some restrictions.
Admission: Free
For more recommendations for New England fall hikes and scenic walks visit our Dog Friendly Places page.
