Cool and Quirky NYC Tours for Locals and Curious Visitors
New York City is full of surprises. Beyond the classic landmarks and well-worn tourist routes lies a city bursting with hidden stories, eccentric guides, and offbeat adventures. Whether you're a lifelong New Yorker looking to shake up your routine or a first-time visitor craving something more memorable than a hop-on hop-off bus ride, these cool and quirky NYC tours will show you a side of the city most people miss.
Prohibition and Speakeasy Tour: Hidden Bars with a Backstory
Image courtesy of Get Your Guide
The Prohibition and Speakeasy Tour takes you beneath the surface of tourist-heavy Manhattan to uncover secret bars, hidden entrances, and the rebellious spirit of the 1920s. Each stop along the route is more than just a place to grab a cocktail—it’s part of a narrative that weaves together history, culture, and expertly mixed drinks.
Led by a savvy local guide with a passion for storytelling (and spot-on drink recommendations), this tour introduces you to vintage-inspired bars with real Prohibition-era roots and quirky twists. One might be tucked behind an unmarked door; another might be disguised as a piano showroom. Each location fits the theme but feels totally distinct, giving you a curated taste of NYC nightlife that’s both immersive and intimate.
This is a unique NYC tour is a bar crawl that combines history with social connection. You’ll meet fellow explorers from around the world, making it one of the more unusual NYC experiences that’s perfect for solo travelers or outgoing locals. And just because the tour ends doesn’t mean the night has to; your guide offers bonus recommendations for late-night stops to keep the adventure going.
If you're looking for cool things to do in NYC that go beyond the ordinary, raise a glass to this hidden-gem tour through the city’s spirited past.
Gangsters and Ghosts Tour: Haunting Histories and Notorious Names
Step into the shadowy corners of New York’s past on the Gangsters and Ghosts Tour, where true crime meets the supernatural in some of the city’s most storied neighborhoods. Winding through Chinatown, Little Italy, and beyond, this tour takes you on a journey from centuries-old secrets to modern-day mysteries, all brought to life by an expert guide who knows how to spin a story.
Instead of a boring description of facts and dates, this is history with grit and personality. You’ll hear about infamous mob families, the turf wars that shaped downtown Manhattan, and the lingering spirits said to haunt the city streets. Whether you're fascinated by organized crime or curious about NYC’s ghostly lore, this tour hits that sweet spot.
What makes it one of the most unique NYC tours is its ability to entertain a variety of interests, from true crime buffs to history lovers, and also all ages, from curious kids to sharp-eyed grandparents. The pace is thoughtful and the storytelling is engaging; the guide makes a point to connect with each participant.
If you're on the hunt for unusual NYC experiences that go well beyond the surface, this gangster-and-ghost combo is one of the coolest things to do in NYC, and a memorable way to explore the city’s darker, more mysterious side.
Bowery Boys Gilded Age Mansions Tour: Scandal, Splendor, and Secrets of Old New York
If you’ve ever walked past the grand limestone façades lining Fifth Avenue and wondered who lived there—and what kind of drama unfolded behind those stately doors—the Gilded Age Mansions Tour by the Bowery Boys is your portal to New York’s most opulent (and outrageous) era.
The Bowery Boys are legendary among NYC history buffs. What began as a popular podcast has grown into a trusted brand for in-depth, entertaining, and deeply researched storytelling about the city’s past. Their walking tours are hosted by expert guides who blend architectural insight, historical context, and juicy turn-of-the-century gossip in a way that feels both enlightening and wildly entertaining.
This two-hour tour dives into the wealth, ambition, and absurd extravagance of the late 19th century, focusing on the ultra-rich families—the Astors, the Vanderbilts, and their social rivals—who built palatial homes along Millionaire's Row. You’ll learn why Fifth Avenue became the epicenter of power and prestige and hear tales of social-climbing scandals that wouldn’t be out of place in a soap opera. Even if you’ve lived in New York for decades, this tour reveals fresh details and hidden histories that bring a familiar neighborhood to life in unexpected ways.
If you’re searching for cool tours in NYC that blend history, gossip, and grandeur, let the Bowery Boys walk you back to the Gilded Age, where fortunes were made and rules were broken.
Catacombs by Candlelight: Secrets Beneath St. Patrick’s Old Cathedral
Image courtesy of Get Your Guide
Tucked away in the heart of Little Italy, far from the towering spires of Midtown, St. Patrick’s Old Cathedral offers a quiet, soul-stirring alternative to the typical NYC tour. This beautifully preserved basilica—one of only 93 in the United States—was the original St. Patrick’s Cathedral before the more famous one on Fifth Avenue stole the spotlight. It’s a place steeped in history, faith, and mystery, and beneath it lies something even more fascinating.
The Catacombs by Candlelight Tour grants rare access to the underground vaults of this 200-year-old church, where New York’s early Catholic elite, bishops, and prominent families were laid to rest. As you descend into the candlelit catacombs, a knowledgeable guide walks you through the rich history of the cathedral, Irish and Italian immigration, and the struggles of early Catholics in a sometimes-hostile city.
The setting is serene and atmospheric, a world away from the bustle of nearby SoHo. Whether you're drawn by heritage, architecture, or curiosity, the tour offers a peaceful, thought-provoking experience that invites reflection and wonder. The church grounds themselves are gorgeous, and the tour length is just right: enough to immerse you in the story without feeling rushed.
For those who love history, hidden spaces, and spiritual stillness, this is one of the most unusual NYC experiences you can have. Even longtime locals are often surprised by the depth of stories preserved here.
Cats About Town: A Brooklyn Heights Walking Tour for Feline History Buffs
If you thought New York’s most fascinating historical figures all walked on two legs, think again. The Cats About Town Tour through Brooklyn Heights is a lovingly quirky deep dive into the city’s feline past—where meows, myths, and Manhattan’s early days all come together in a uniquely delightful stroll.
Led by knowledgeable and charismatic guides, this walking tour offers a fresh way to explore one of Brooklyn’s most picturesque neighborhoods. But instead of focusing solely on the typical architectural or political history, you’ll hear engaging stories of NYC’s historic cats, from church-dwelling mousers to literary companions who once prowled the brownstones of Brooklyn Heights. It’s not just for cat lovers, either. The tour is packed with insights about New York and Brooklyn’s broader history, making it one of the most unusual NYC experiences you can have without leaving the sidewalk.
Equal parts informative and whimsical, this tour is a joyful way to spend an afternoon in a historic neighborhood with like-minded explorers. If you're searching for cool things to do in NYC that combine local charm, a scenic walk, and stories you won’t hear anywhere else, this unique NYC tour is truly the cat’s meow.
Watson Adventures High Line Hijinks Scavenger Hunt: Team Up for Trivia, Clues, and City Secrets
If you think you know the High Line, think again. This interactive adventure will have you scanning sculpture, peeking into parks, and decoding bizarre facts you never noticed before. The High Line Hijinks Scavenger Hunt, run by Watson Adventures, is part walking tour, part trivia challenge, and 100% fun. It's a perfect mix of brainy entertainment and city exploration, making it one of the most unique NYC tours you can take.
Unlike traditional tours, this experience is all about teamwork and discovery. You won’t be collecting items, but rather solving clever, often hilarious clues that point to offbeat details hidden in plain sight. Designed for sharp minds and curious eyes, this is an all-ages-friendly activity that prioritizes fun over competition. And while there are winners (and medals!), the real prize is laughs, inside jokes, and valuable memories.
Hosted live by professional guides for a truly personalized experience, the hunt weaves together the High Line’s art, architecture, and stories into a dynamic, puzzle-filled journey. Public hunts are somewhat limited, but if you’re able to rope in some friends or family, Watson Adventures also offers private hunts that can be customized for your group. For something off the beaten path, but still right in the heart of Manhattan, this unusual NYC experience delivers a memorable mix of mystery, collaboration, and laughs.
Discover Green-Wood Cemetery Trolley Tour: Art, History, and Quiet Wonder in Brooklyn
Green-Wood Cemetery isn’t just a place of rest, it’s a place of beauty, legacy, and storytelling. Founded in 1838 and now a National Historic Landmark, Green-Wood was one of the first rural cemeteries in America and helped inspire the creation of Central Park. Today, it’s not only a working cemetery but also a revered cultural landscape filled with world-class sculpture, historic monuments, and sweeping skyline views.
The Discover Green-Wood Cemetery Trolley Tour offers a serene and informative way to experience this 478-acre wonder. With no bikes, jogging, or loud music allowed, the cemetery maintains a peaceful and pastoral setting. The tour, led by expert guides who know the grounds inside and out, shares the stories of the inventors, Civil War generals, and famous New Yorkers buried here, including Leonard Bernstein, Jean-Michel Basquiat, and “Boss” Tweed. As you roll past Victorian mausoleums, centuries-old trees, and one-of-a-kind sculptures, the guide brings the space to life with storytelling, historical insights, and sometimes even a song.
More than just a cemetery, Green-Wood is also a certified arboretum, home to thousands of trees and a diverse ecosystem that makes it a haven for bird watchers, photographers, and anyone craving a break from the city's nonstop energy. Every season offers its own beauty, from spring blooms to autumn color.
For those looking for unusual NYC experiences with heart and depth that’s far off the tourist trail, this trolley ride through Green-Wood is a journey well worth taking.
Conclusion
New York City is full of iconic sights, but sometimes the most memorable experiences happen when you veer off the well-trodden path. Each of these experiences reveals a quirky and unexpected facet of the city. They're not just tours, but invitations to connect more deeply with New York’s layered past, vibrant present, and endlessly fascinating neighborhoods. So skip the long lines and tourist traps. Choose the kind of NYC adventure that leaves you with wide eyes, weird facts, and a story worth retelling. After all, the best way to fall in love with New York—again, or for the first time—is to see it from a new angle.
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