Pull Over for These Roadside Gems Along the Drive in Connecticut
A different way to beat the holiday traffic.
There are stunningly beautiful states. There are fly-over states. And then there are drive-through states. And despite all of Connecticut’s incredible contributions to the world—the cotton gin, the frisbee, the can opener, Ang Lee’s seminal 1997 film the Ice Storm, UConn Women’s Basketball, the submarine, the submarine SANDWICH—the New England mainstay is, undoubtedly, the epitome of a drive-through state. Whether you’re hustling over to urban hubs like New York and Boston or trekking north for an outdoorsy Vermont, Maine, or New Hampshire getaway, the Nutmeg State is rarely any roadtripper’s final destination.
But that doesn’t mean there’s nothing to do around these parts. On the contrary, Connecticut is teeming with curious roadside diversions—the perfect antidote to battling the traffic slowdowns inevitably clogging up the Merritt, I-91, or I-95. From dining at the birthplace of the hamburger and browsing books amid livestock to exploring a 19th-century seafaring village, saluting a decorated war dog, and touring Mark Twain’s ornate gothic home, here’s a list of monumental pit stops in Connecticut that are more than worthy of a little detour.
Hartford
Mark Twain penned his most famous works while living in Hartford, Connecticut, including The Adventures of Tom Sawyer, The Prince and the Pauper, and Adventures of Huckleberry Finn, to name a few. And at his stately home-turned-museum, visitors can hop on guided tours through the rooms where the magic happened. Explore the 1874 American High Gothic style that has been preserved and restored over the years, and venture around the garden where the “Huckleberry Candy” flower is planted. Come by the museum for the exhibits about and inspired by Twain—then stay for the six-foot LEGO replica of the iconic author.
Bristol
This would be Mary Poppins’ dream roadside attraction, if there ever was one. The New England Carousel Museum is dedicated to preserving and celebrating over 100 years of antique wooden carousels. Horses of all shapes, sizes, and colors are on display in the permanent collection. Or you could take a ride on the Venetian indoor carousel, check out touring exhibits, or schedule your visit to coincide with a fun and festive seasonal event.
Niantic
This three-location operation is known as a “bibliophile’s bliss,” and with roughly half a million books in stock, the title is fitting. Make sure you visit the original location, the Main Barn, which first opened in 1988. The multi-story space has floor-to-ceiling bookshelves jam-packed with just about every genre, subject, and author you can imagine. The Book Barn purchases new books every day, so the collection is ever growing and no two visits are ever the same. If you’re the kind of person who can get lost for hours in a bookstore, you might want to leave a whole day for this one. Oh—and if you happen to have any old books lying around, bring them along and make a few bucks while you’re at it.
Orange
Few out-of-staters know that there’s a dedicated PEZ visitor center in Connecticut where you can browse, shop, and hear all about the iconic candy dispensers’ sweet, sweet history. Upon arrival, you’re greeted by a massive wall of iconic PEZ dispensers before walking into the main room, where you can buy (then eat) to your heart’s content. The museum opened in 1927 and has been taking visitors through its historical timeline, memorabilia, and DIY PEZ creations (like a motorcycle) ever since. FWIW, we deemed it Connecticut’s weirdest roadside attraction.
New Haven
Proclaimed the birthplace of the hamburger (by the Library of Congress, no less, so you know it’s legit), Louis’ Lunch has been griddling up the good stuff in their patented vertical broilers since 1895. The prime patties arrive sandwiched between two slices of toast and layered with cheese, tomato, and onions—and whatever you do, don’t ask for anything else, including condiments. They serve up their ‘burgs just as they did when they first opened. For sides, choose between potato salad or chips, and dessert is whatever homemade pie they’ve got on that day. Lucky you if they happen to have apple in stock, because it’s *chef’s kiss* delish.
Cheshire
Vintage toy lovers from near and far travel to Cheshire to visit this nostalgic, family-run toy museum. Spice Girl Barbie dolls from the ‘90s? Looney Tunes figurines from a decades-old McDonald's Happy Meal? Odds are, they’ve got them. Owner Gerry Barker inherited the Baker Character, Comic & Cartoon Museum from his parents, Gloria and Herb, who collected toys and childhood artifacts throughout the ‘50s and ‘60s. Today, almost 80,000 pieces are on display, from cast iron elephant ramp walkers that date back to 1873 to Disney memorabilia from the early 1900s, plus a whole shelf dedicated to Beatlemania.
Mystic
Mystic Seaport Museum, the country’s largest maritime museum, takes you back in time via a replicated 1800s seafaring village (think Virginia’s Colonial Williamsburg, but nautical). The physical space is divided into two parts: the Seaport Village with over 40 old-timey shops—from the Mystic Press Printing Office to the Plymouth Cordage Company Ropewalk—and the Shipyard, a working preservation effort that uses historic methods to keep antique vessels afloat (literally).
And right now, you can celebrate the festivities of maritime past at Holiday Magic, a month-long event spanning everything from puppet-making workshops to holiday-themed storytimes by 19th-century residents and a riveting performance from Justin Mazz Magic.
Norwalk
Lean into Connecticut’s dystopic suburban vibes by cruising past the filming location of one of the state’s creepiest blockbusters. This southwestern landmark might have posed as the Stepford Men’s Association in the 1975 film, but today, the castle-esque 1868 property functions as a historical museum with tours open to the public. And this time of year, it goes big for the Christmas season, transforming into the Holiday Wonderland at the Mansion complete with tree displays, a throwback ice skating scene, evening soirees, and more. Just don't let your guard down—you never know what darkness lurks beneath the charming facade…
Hamden
Remember video stores, those once-magical outposts that promised all the fun a Friday night in the ‘90s could possibly muster? Relive your childhood at Best Video in Hamden, where the friendly staff has transformed their VHS-hawking temple into a nonprofit hub dedicated to film screenings, talks, live music, and other cinephile-approved happenings. Wander the shelves for a hearty dose of nostalgia, running your fingers along the 30,000-strong inventory of DVDs, VHS tapes, Blu-Rays, and more—spanning every genre imaginable—before settling in with a coffee from the onsite cafe.
Groton
Continuing on with the movie theme, hungry travelers passing through seaside Mystic can try out their best Julia Roberts impression inside the 1988’s eponymous pizzeria. Sold by the slice or full pie, the grub here lives up to the hype, as does the interior, which is plastered with newspaper clippings, posters, and other memorabilia from the rom-com classic. And after you’ve had your fill of cheesy, saucy goodness, don’t forget to snag your very own Slice of Heaven T-shirt from the small merch section near the bar.
Rocky Hill
Quite possibly Connecitcut’s best kept secret, this Rocky Hill stop-off is a must for any dino-crazed commuter. The attraction got its start back in 1966, when a team of construction workers uncovered what, to their surprise, turned out to be thousands of pristinely preserved dinosaur tracks. Modern visitors can gape at the bird-like fossilized prints inside a geodesic dome, while also interacting with various educational displays and model dinosaurs. To boot, a lush arboretum surrounds the exhibits, lovingly landscaped with many of the same plants that scientists believe would have covered the area during the Mesozoic era.
Middletown
When one envisions a veterans memorial, statues of helmeted troops raising a bronze flag probably spring to mind. But that’s not the case in Middletown, where an unlikely war hero holds court atop a marble podium engraved with his name: Stubby. The beloved army pup proudly served as the mascot to the 102nd Infantry during World War I, following along with drills, tending to wounded soldiers, literally sniffing out enemy attacks, and even learning to salute just like his brothers in arms. Before retiring, he managed to reach the rank of sergeant—becoming the army’s first officially ranked dog—after snagging a German spy and delivering him to the awaiting officers. Pay your respects by posing for a selfie with this tribute to the remarkable canine (the real Stubby lives on in taxidermied form at the Smithsonian National Museum of American History in DC), and don't forget to rub his head to thank him for his service.
Danbury
Back when it debuted in 1901, Danbury’s picturesque Union Station was abuzz with activity. Three different railways found their way to the transportation hub, making it a vital component of the Northeast’s rail system until it closed in 1972. These days, a group of devoted volunteers have rescued the site from quiet disrepair, revitalizing its stockyard and offering memorable tours, rides, and talks to curious visitors all year-round. And the station wasn’t the only thing the volunteers rescued—when the fairy tale Magic Forest theme park in Lake George, New York shuttered in 2018, the Danbury Railway Museum snatched up a 38-foot-tall, 4,500-pound fiberglass replica of Uncle Sam the theme park had purchased from the long-gone Great Danbury State Fair nearly 40 years before. An unusual pairing, maybe, but when you’re rolling along in a decked out holiday steam engine and marveling over the might of America’s once-thriving railroads, it’s hard not to feel a twinge of patriotism.