Humans are weird. Tell us we have to drive for a couple hours in a cramped car and for many of us, it’s a death sentence commute. But give us snacks, the right people and some quirky stops along the way and suddenly, it’s “Road trip—Yay!” 

Remember when roadside attractions were strictly word of mouth, and maps were tangible accessories associated with the passenger seat and its navigational duties? Me neither.

Thanks to the stalwart efforts of three “road trip know-it-alls” Doug Kirby, Ken Smith and Mike Wilkins, Roadside America has been the road tripper’s quirky companion since 1992. First published as a book, the project of mapping the country’s weird, creepy, cute and hilarious roadside creations has evolved into an interactive website (roadsideamerica.com) and app where oddity enthusiasts anywhere can submit entries, tips and updates. 

And you better believe we’ve got more than our fair share of odd in the mountains. 

CONNECTICUT

Kent: Sculpturedale

This four-acre yard up Highway 7 hosts more than 100 free-range steel sculptures by artist Denis Curtiss. The studio and garden gallery are open on weekends or by appointment year-round.

Woodbury: Leslie Murray’s Junk People

This is what happens when an artist marries a mechanic: She takes his scrap metal and not only makes the quirkiest, sweetest sculptures in town, but she becomes a skilled welder in the process. Look for Murray Brothers Garage, and if you’re walking around town, see if you can spot some other pieces of hers in various places. 

Goshen: Action Wildlife Taxidermy Exhibit

This outdoor wildlife park is the only place I know of that lets you pet a zebra. Live animals roam outside or in the petting zoo, and inside, some of the highest quality taxidermy of African animals you’ll ever see (if that’s your bag).

NEW YORK

Hillsdale: Giant Chair

This extremely well-constructed eight-ft.-tall chair (which would make for a very cute photo op) was donated for the opening of the Roeliff Jansen Community Library by artist Leon Smith in 2010. I guess it didn’t fit inside.

Spencertown: Giant Head Sculpture

Ah, a peaceful drive down the Taconic, where there’s scenic hillsides, lovely trees—and a giant white head. This head of Gaea (Mother Earth) is 20 feet tall and just the beginning of a treasure trove of Roy Kanwit’s Taconic Sculptures. The sculpture park just reopened earlier this year, so take this chance to stretch your legs and check these out up close. You’ll be glad you did.

Cairo: Unicorn Statue

If you’re traveling with a kiddo who’s fascinated by magical beasts, this absolutely random unicorn statue at the corner of South Road and Mountain Avenue may pique their interest. 

East Durham: Giant Steampunk Robot

Built by Thomas Willeford for the 2014 Steampunk World’s Fair, this 17-ft.-tall robot at Blackthorne Resort is worth a detour. The artist someday wants to build an even bigger one that he can sit inside to operate the controls. Can you imagine?

Woodstock: Drip Candle Mountain

OK, so it’s basically a candle, but, hear me out: It’s been drip-forming for more than half a century. Started in 1969, this eight-ft.-tall wax mountain is a beautifully trippy link to the Woodstock of yesteryear. 

Boiceville: Steve Heller’s Spaceships And Robots

Hey, we know that guy! Doesn’t his wife (Martha Frankel) write for us? Well, we found this stop on our own, and nepotism or no nepotism, we’d definitely take the detour to check out these other-worldly crafts. 

Mount Tremper: World’s Largest Kaleidoscope

Sometimes, when you love something, there’s only one thing you can do: make a really, really big one. 

Highland/Poughkeepsie: Walkway Over The Hudson

The world’s highest and longest pedestrian bridge deserves a visit if this isn’t your neck of the woods. Walk more than a mile at 212 feet above the Hudson River with gorgeously unobstructed views of the scenery. Defies description for its beauty.

Red Hook: Old Rhinebeck Aerodrome

This campy airshow isn’t just a detour—make this a destination on your itinerary. Started in 1960 by James Henry “Cole” Palen Jr., the show is a World War I melodrama designed to show off the old timey airplanes that Cole loved so much. 

Red Hook: Fork In The Road

OK, Stephen Schreiber, we get the fork in the road joke, and once you have a giant fork you might as well add a spoon…but why is there also a giant Prozac capsule?! This is unhinged, and we love it. So much. 

Mountainville: Giant Three-Legged Thing On Big Human Head

While it does have a great name, this 28-foot copper and steel sculpture by Chinese artist Zhang Huan is officially titled “Three-Legged Buddha.” 

Kerhonkson: World’s (Third) Largest Garden Gnome

Gnome Chomsky (as he is known) was created in 2007. Since then, two other garden gnomes have apparently surpassed his size (jealous, much?). But to us, he’ll always be the original World’s Largest Garden Gnome. 

Bethel: Hippie Muffler Man

OK asking for a friend: is he single? He’s got the facial hair and build of a lumberjack, the beanie of a third-tier barista and the wardrobe of an indie lead singer who did just as well in 1969 as he would do today on TikTok. Wait, are these red flags? If your road trip leads you cross-country, you might make a go at catching ’em all—you can find a map of all the muffler men on the Roadside America website.

Saugerties: Giant Steel Dinosaur Skeleton

If you like camping and dinosaurs (or your little one does), reserve a campsite at Rip Van Winkle Campgrounds so you can gawk at this giant steel Apatosaurus/T. Rex skeleton mash-up. 

Millbrook: Wing’s Castle

Thanks to artists Peter and Toni Wing, this storybook fantasy castle not only exists, but it also exists right here in the mountains. You can even stay in the cottage on site overnight. Swoon.

MASSACHUSETTS

Amherst: Hope The Cow

This charming life-sized piggy bank (cow bank?) built out of propane and oil tanks by local artist Kamil Peters in 2013 invites passersby to deposit cash donations that help fund Craig’s Place, a local homeless shelter. Bless you, Hope. 

Lee: Big Beaver

It’s like I always say, “Nothing sells self-storage quite like a giant goofy beaver on a wagon.” Visible on the side of the road as you drive by the north side of Highway 20, this 20-ft.-tall relic from a family-owned auction and antique business that pivoted to self-storage was built with a chicken wire frame and stuffed with hay. 

Tyringham: Santarella: Gingerbread House

Once a passion project for English sculptor Henry Hudson Kitson, this fairy-tale inspired home is now under the care of two new and dedicated owners who are trying to figure out how to repair its one-of-a-kind roof. Stay on the property in the renovated tower structure on Airbnb or drive by and gawk. They’re used to it. 

Pittsfield: Wally The Stegosaurus

Well, thanks to his signage, we know how Wally came to be: “Wally was the second Stegosaurus from the mold made by the Louis Paul Jonas Studios of Hudson, NY (The first went to the New York World’s Fair in 1963 for the 1964 opening).” Now if someone could just tell us why. 

Williamstown: Eyes On The Campus Lawn

It’s art celebrating art…with a whole bunch of eyes. Iconic artist Louise Bourgeois created these sculptures which have found home on Williams College’s grounds since 2001. Best to visit these massive heavy-lidded eyeballs at night, when their irises glow blue. 

Greenfield: Gravity Hill

Get in, Scully, we’re going to defy gravity. The horizontal yellow mark on this road marks the spot to stop your car. Put your car in neutral, and your car will supposedly roll uphill backwards, all the way up the hill. I want to believe!

Middlefield: “It” Gravestone

Ready for something a bit creepy? Behind the town hall in Middlefield (once the site of an elementary school), along the north tree line, there’s a cryptic gravestone that just says “IT” carved into it by hand. There are several theories about who (or what) is buried there, but consensus also tells us that if this gravestone isn’t haunted, a mansion across the road from it almost certainly is.