Fall makes a fine excuse to take the scenic route, especially when it leads to a staircase with no house, a castle full of peculiar locks, or a giant face waiting in the woods. These eight strange places offer a mix of outdoor wandering and indoor monster watching for an autumn day away.
1. Madame Sherri Forest
Chesterfield, New Hampshire
A staircase in the woods is an excellent way to make a perfectly ordinary walk feel suspicious. At Madame Sherri Forest, the stonework outlasted the French-inspired summer house that costume designer Antoinette “Madame Sherri” Bramare built in 1930. The parties are long over; the foundation, chimney, and battered stairs still make quite an entrance.
For a fall outing, the appeal is simple: a short woodland walk with an unexpectedly grand ruin at the end. A longer loop heads toward Indian Pond. Admire the masonry from the trail. Part of the staircase collapsed in 2021, and unsafe areas are roped off.
Explore Madame Sherri Forest in the Oddities Directory.
2. Hope Cemetery
Barre, Vermont
A granite race car sounds like something that belongs beside a highway. At Hope Cemetery, it belongs to a much more personal collection. Barre’s stoneworkers turned memorials into objects as individual as the people they honor, including an easy chair, a soccer ball, and an airplane.
This is a thoughtful stop for a quiet autumn afternoon, especially if you like spotting details instead of rushing through a checklist. The cemetery dates to 1895 and doubles as a remarkable display of the craft that shaped Barre. It remains a working cemetery, so give mourners space and treat the monuments with care.
Explore Hope Cemetery in the Oddities Directory.
3. Witch’s Dungeon Classic Movie Museum
Plainville, Connecticut
If your idea of fall involves an old monster movie, here is a chance to step closer to the screen. Dracula, Frankenstein’s monster, and the Creature from the Black Lagoon are among the figures at the Witch’s Dungeon Classic Movie Museum. Founder Cortlandt Hull began the attraction as a teenager in 1966.
The displays draw on life casts, measurements, costumes, and practical effects rather than a box of disposable Halloween decorations. Vintage toys and film memorabilia add to the appeal. Opening dates are limited and can be seasonal or event-based, so confirm a visit before making this the centerpiece of a road trip.
Explore Witch’s Dungeon Classic Movie Museum in the Oddities Directory.
4. Gillette Castle
East Haddam, Connecticut
William Gillette helped bring Sherlock Holmes to the stage, then built himself a home with plenty of its own mysteries. Gillette Castle has forty-seven doors with individually designed locking mechanisms, hidden mirrors for watching visitors, and a concealed bar. Even the latches got the theatrical treatment.
Outside, the estate sits above the Connecticut River, with walking paths following parts of Gillette’s former narrow-gauge railroad route. That combination makes it a satisfying fall stop whether you come for an eccentric house or a walk around the grounds. Interior tours run on a schedule and tickets can sell out; check seasonal access before going.
Explore Gillette Castle in the Oddities Directory.
5. Hammond Castle
Gloucester, Massachusetts
A medieval-looking castle on the Massachusetts coast is strange enough. Add a radio-control inventor’s laboratory and the story gets better. John Hays Hammond Jr. built Hammond Castle in the late 1920s, combining a home, a museum, a research space, and his appetite for old architectural fragments.
Towers, courtyards, and dramatic rooms make this a good choice when your autumn plans call for a little Gothic scenery. The experiments behind those walls give the visit more substance than a handsome facade. The museum operates seasonally with ticketed visits, so check its dates and entry arrangements before heading to Gloucester.
Explore Hammond Castle in the Oddities Directory.
6. Ha Ha Tonka Castle
Camdenton, Missouri
The Lake of the Ozarks has a castle with no roof and an unusually good view. Businessman Robert McClure Snyder began the mansion in 1905; his family completed it, and a 1942 fire left the stone walls open to the sky. Towers and arches now frame the lake and the park below.
For a fall day outside, you can pair the short walk to the ruins with trails through a landscape of sinkholes, cliffs, and a natural bridge. Park admission is free, though trail lengths and difficulty vary. Stay on marked paths and respect the barriers around the fragile masonry.
Explore Ha Ha Tonka Castle in the Oddities Directory.
7. Dismals Canyon
Near Phil Campbell, Alabama
Dismals Canyon sounds gloomy. Its sandstone passages, mossy rock walls, and waterfalls make a much more inviting case. By day, a trail winds through the canyon floor past boulders and rock shelters. By night, tiny blue-green lights can appear on the walls.
Those lights come from fungus gnat larvae known as dismalites. They give this fall detour a strange little twist, but they are living insects with their own timetable. Night viewing requires a guided tour during suitable parts of the year, and weather and temperature affect the display. Confirm tour availability instead of counting on a guaranteed glow.
Explore Dismals Canyon in the Oddities Directory.
8. Ninigret Park Trolls
Charlestown, Rhode Island
A walk with a giant troll at the end has a strong advantage over a walk with only your step count at the end. At Ninigret Park, Erik Rock and Greta Granite sit in separate spots, turning a visit into a small scavenger hunt through ponds, trees, and boulders.
Thomas Dambo and his team built the roughly sixteen-foot figures from reclaimed and recycled wood in 2024. They make a playful choice for a fall outing, especially with someone who needs a reason to keep walking. The trolls are free to visit; follow designated routes and the park’s current parking guidance.
Explore Ninigret Park Trolls in the Oddities Directory.
Before you set out, check the access notes for your chosen stop. A forest trail and a seasonal museum require different plans, and a night tour needs a little more thought than an afternoon stroll. Pick the kind of strange you want, pack an extra layer, and give yourself time to look around.