Discover why New Haven, Connecticut, makes for a memorable weekend getaway
At the age of 30-something, I finally ticked off a life milestone: my very first flight. And where did it take me? None other than the historically rich, pizza-blessed streets of New Haven, Connecticut.
Departing from airports in Greenville, Raleigh, and Wilmington, Avelo Airlines finally added service from Charlotte to New Haven in May 2024. With four weekly flights from Concord, this low-cost airline made our trip easy – and affordable.
It only took the word “Pizza” to get Michael on board. Armed with commemorative boarding passes, we were off to explore a city that has now carved out a special spot in our hearts – and hopefully, soon, yours.
Back home now, I’m thrilled to pass on everything we uncovered in New Haven. Whether or not you hop on a first flight to get there, this New England gem is perfect for a weekend retreat. Here’s why you should consider it.
GETTING TO KNOW NEW HAVEN
Long before it was bustling with Yale students and pizza lovers, New Haven was home to the Quinnipiac people. They stewarded the land until 1638, when Puritan settlers arrived and purchased it to build one of America’s earliest planned communities.
Their design was revolutionary: a nine-square layout centered around a communal green space. That green, the New Haven Green, still exists today, a living testament to the city’s unique legacy. Not long after, Yale University (originally the Collegiate School) was founded in 1701, putting New Haven on the map as an intellectual hub.
Thanks to its prime location along the Long Island Sound, New Haven blossomed into a busy port and industrial center. Like many northeastern cities, it faced tough economic times during the mid-1900s, but it has since rebounded. Today, it blends Ivy League prestige with a vibrant arts scene and rich multicultural identity, earning its title as Connecticut’s third-largest city.
TOP REASONS TO VISIT
Sitting roughly two hours from Boston, Providence, and New York City, New Haven is a prime destination for a quick, culture-packed trip. It offers a dynamic mix of old-world charm and modern-day liveliness, especially thanks to the influence of its most famous resident: Yale University.
Whether you’re into historic architecture, museums, food, or just some good old-fashioned walking and wandering, you’ll find it here. The compact downtown area is ideal for pedestrians, making it easy to hop from library to lunch spot without ever needing a car. It’s truly one of those cities where every block feels like its own adventure.
UNMISSABLE EXPERIENCES IN NEW HAVEN
Smart travel tip: Some of the city's most exciting attractions are free!
Dive Into Rare Book Heaven
Step into the surreal glow of the Beinecke Rare Book & Manuscript Library, one of the world’s most revered repositories for the printed word. From Gutenberg Bibles to Chipotle-branded ephemera, this place houses it all—literally, centuries of human creativity and knowledge tucked behind translucent marble panels.
Admission is completely free. Visitors can circle the central column of rare books and peek at rotating exhibitions that have included everything from Frederick Douglass writings to illuminated manuscripts. If you’re a bibliophile, this is sacred ground. Just be aware: there are no restrooms, and you can only explore the exhibit hall unless you’re a registered researcher.
→Beinecke Rare Book and Manuscript Library // 121 Wall St, New Haven, CT 06511
Take a Walk with Yale
Want to understand New Haven? Start with Yale. Join a free guided tour led by current undergrads and uncover the layers of tradition, innovation, and quirky lore that permeate campus life. From Gothic architecture to ultra-modern dorms without right angles (looking at you, Morse College), this hour-long experience paints a vivid picture of life at one of the world’s most prestigious universities.
Stops include Yale’s oldest buildings, famous statues, and the iconic Sterling Memorial Library. While you won’t step inside most structures during the tour, the exteriors alone are worth the stroll. And the guides—often overflowing with energy and humor—add personal touches that make this far more than just a history lesson.
Pro tip: Book your spot online in advance and choose the visitor tour (not the prospective student version). Prepare for 60–90 minutes of walking and chatting—plus zero restroom breaks, so plan accordingly!
→Yale Visitor Center // 149 Elm St, New Haven, CT 06511
Dig Into Prehistoric Wonders
After a years-long transformation, the Yale Peabody Museum has reopened—brighter, better, and bursting with stories from Earth’s ancient past. Inside, you’ll encounter colossal dinosaur skeletons, glittering gems, and rotating exhibits on everything from climate to culture.
The Burke Hall of Dinosaurs steals the show with life-size brontosaurs and stegosauruses that inspire awe (and a few laughs with their cartoonish postures). But don’t skip the other levels: 60,000 minerals shimmer in cases upstairs, while butterflies flit gracefully in the entomology display.
Pro tip: Admission is free, but advance online reservations are required due to high demand. If you’re spontaneous, try walking in—last-minute tickets might be available at the door.
→Yale Peabody Museum // 170 Whitney Ave, New Haven, CT 06511
Wander Through Artistic History
New Haven’s rich cultural offerings continue at the Yale University Art Gallery, America’s oldest university-affiliated art museum. With over 180,000 pieces, this gallery is a treasure trove of global art—from ancient Mesopotamian sculptures to bold modern paintings.
During our visit, we barely scratched the surface in ninety minutes. You’ll want to plan your route using their app so you don’t miss your favorites. Best of all? Admission is completely free, and the museum provides lockers and coat checks for stress-free browsing.
→Yale University Art Gallery // 1111 Chapel St, New Haven, CT 06510
SHOP LOCAL IN NEW HAVEN
Forget the big brands—New Haven's indie shops are bursting with charm and character
Find a Piece of New Haven to Take Home
Looking for a souvenir? The Yale Bookstore and Campus Customs have the gear if you want to rock Ivy League pride. But if your taste leans artsy, check out Strange Ways for funky patches or dwell New Haven for curated home décor.
One must-stop is East Street Arts, where every purchase supports artists with disabilities. It’s a heartwarming experience and a great way to give back while grabbing something meaningful.
→Campus Customs // 57 Broadway, New Haven, CT →dwell New Haven // 1022 Chapel St →East Street Arts // 597 East St →Strange Ways // 151 Orange St →The Yale Bookstore // 77 Broadway
Experience New Haven at the Farmers Market
New Haven’s CitySeed Farmers Markets are far more than just produce stands. Held in various neighborhoods seasonally, they offer an exciting mix of local bounty—from farm-fresh vegetables and fruits to baked goods, flowers, artisanal snacks, and more.
What makes them unique? They’re producer-only markets, meaning every vendor grows, bakes, or crafts their items locally in Connecticut. It’s a guarantee of authenticity—and an invitation to discover new seasonal delights every weekend.
Note: Market days and locations rotate based on the season, so check the CitySeed website for the latest schedule before your visit.
→CitySeed Farmers Markets // Various Locations
TASTE YOUR WAY THROUGH NEW HAVEN
Forget what you thought you knew about pizza—this city might just change your life
The Apizza Pilgrimage
Let’s cut to the cheese—pizza (or apizza, as it’s lovingly known here) is New Haven’s culinary crown jewel. Pronounced “ah-beetz,” this local variation features ultra-thin crusts with a signature char, minimalistic toppings, and plenty of chewy, smoky magic from coal-fired ovens.
The holy trinity of New Haven apizza? That would be Pepe’s, Sally’s, and Modern. Each has fierce loyalists, century-old recipes, and waits that are always worth it.
- Pepe’s — The original since 1925, best known for its white clam pie.
- Sally’s — A family offshoot of Pepe’s, revered for its tomato sauce and charred crust.
- Modern — Slightly different, slightly softer crust, but still divine. A locals’ favorite.
Cheese is optional. Slices are rare (except late nights at BAR). What’s guaranteed? Flavor, tradition, and a pie you’ll crave long after you’ve left.
→Frank Pepe Pizzeria Napoletana // 157 Wooster St →Sally's Apizza // 237 Wooster St →Modern Apizza // 874 State St →BAR // 254 Crown St →Da Legna at Nolo // 687 State St →Zeneli Pizzeria e Cucina Napoletana // 138 Wooster St
Eat Good, Do Good
Havenly isn’t just a café—it’s a cause. This warm and vibrant spot in downtown New Haven hires and trains refugee and immigrant women, offering empowerment through culinary creativity.
The menu is a mix of global flavors with dishes rooted in Middle Eastern and North African traditions. Try the Istanbul Street Bites or Falafel paired with rich, smooth hummus. And don’t leave without a dessert or two—the cardamom tea and pistachio-stuffed Tamriyeh are unforgettable.
→Havenly // 25 Temple St, New Haven, CT
Bagels Worth the Hype
At Olmo, bagels aren’t just breakfast—they’re an experience. Their cacio e pepe bagel? Revolutionary. In 2023, they out-bagelled New York bagel shops to win at the New York BagelFest.
Come for the classics, stay for the specials like the Everything Everything flavor or a monthly creation that’s as inventive as it is delicious. You can turn your bagel into a sandwich or enjoy it with schmears that range from classic to culinary adventure.
→Olmo // 93 Whitney Ave, New Haven, CT
FINAL THOUGHTS
New Haven isn’t just another college town—it’s a vibrant destination teeming with history, culture, community, and flavor. From ancient texts to apizza, every block offers something new to uncover. Whether it’s your first visit or your fifth, this city has a way of making you feel like you’ve just discovered something truly special.
So pack light, bring an appetite, and let New Haven surprise you. You might just find yourself planning the next trip before the weekend’s even over.
