Best Places to Visit in Connecticut
While living in NYC for 10 years, I traveled to Connecticut often and I always loved it. For a small state, it holds such variety. You will find coastal towns where the breeze speaks in poetry, bustling cities with hidden museums and old secrets, and quiet villages that feel like time never quite caught up.
After spending time traveling across this compact yet diverse state, I’ve narrowed it down to the places that left the biggest impression on me. Whether you're in search of stillness, beauty, or just a really good meal with a view, there's something here waiting for you.
1. Greenwich
This historic riverside town (often called the “First Town in America”) instantly charmed me, a small city with a refined yet welcoming vibe, historic architecture, leafy avenues, and its iconic views over the Long Island Sound. With its colonial heritage, elegant homes, and lively downtown, I could see why it’s often ranked among the most beautiful places to live in the U.S.
From New York City, I drove about 50 minutes northeast along the coast and stayed two days in Greenwich at Delamar Greenwich Harbor!
I explored the Bruce Museum’s eclectic art and natural history exhibits, strolled the manicured landscapes of Greenwich Point Park, admired 19th-century cottages and grand estates in the historic districts, and wandered through the polished shops and cafés along Greenwich Avenue. In the evening, I capped it off with fresh New England seafood at Elm Street Oyster House, where the lobster bisque was a true highlight for me!
A downside? Parking near the Avenue on weekends was tricky. I circled longer than I wanted before finding a spot.
2. Hartford
This historic New England capital (often called the “Insurance Capital of the World”) surprised me with its mix of old-world charm and modern energy — a city where historic homes and cultural landmarks meet a lively downtown and riverside parks. With its deep literary roots and grand architecture, it felt like walking through American history while still discovering a vibrant present.
From Greenwich, I drove about an hour and twenty minutes north along I-95 and I-91 and spent two days in Hartford at the elegant Goodwin Hotel — a romantic boutique property blending Victorian architecture with contemporary flair!
I toured the Mark Twain House & Museum, where the author penned some of his most famous works, and stepped next door into the Harriet Beecher Stowe Center to learn about the writer’s abolitionist legacy. I strolled through Bushnell Park — America’s oldest publicly funded park — admiring its Gothic Soldiers & Sailors Memorial Arch, and wandered the galleries at the Wadsworth Atheneum, the oldest public art museum in the United States. In the evening, I capped it off with modern Italian comfort food at Salute, where the butternut squash ravioli was a true highlight!
3. Old Saybrook
This coastal gem — one of Connecticut’s oldest towns — instantly won me over with its historic charm, seaside air, and relaxed New England vibe. Nestled at the mouth of the Connecticut River where it meets Long Island Sound, Old Saybrook has a timeless grace: tree-lined streets, antique homes, and the lingering romance of Katharine Hepburn, who made her home here.
From Hartford, I drove about 50 minutes south and stayed two days at the iconic Saybrook Point Resort & Marina — a romantic waterfront escape with sweeping harbor views and cozy, nautical style.
I wandered through Main Street’s boutiques and colonial buildings, toured the General William Hart House, and explored the sweeping grounds of the Katharine Hepburn Cultural Arts Center (affectionately called “The Kate”). Afternoons were spent walking the boardwalks of Harvey’s Beach, dipping into antique shops, and savoring the salty breeze along the causeways. In the evenings, I capped it off with fresh seafood at Liv’s Oyster Bar, where the lobster roll was the highlight of the trip!
A downside? Parking near the beach was limited. I spent more time looping through side streets than I wanted before finally settling in to enjoy the sand.
4. Stonington
This historic seaside village at the state’s southeastern tip felt like stepping into a postcard — a charming blend of salt air, colonial-era homes, and cobblestone streets that whisper stories of New England’s maritime past. With its working harbor, vineyard-dotted countryside, and colorful clapboard houses, Stonington has a graceful, timeless appeal.
From Old Saybrook, I drove about 40 minutes east along the coast and spent two days at the romantic Inn at Stonington — a cozy waterfront inn with sweeping harbor views and fireside charm.
I wandered Water Street’s boutiques, cafés, and 18th-century homes, explored the Old Lighthouse Museum perched on the edge of the breakwater, and strolled through the peaceful Stonington Borough with its weathered charm. In the afternoons, I toured Saltwater Farm Vineyard (a converted WWII airplane hangar turned vineyard), and capped the evenings with dinner at Noah’s Restaurant — where the Portuguese-inspired seafood stew was unforgettable!
5. Guilford
This classic New England town, set along Connecticut’s shoreline, charmed me right away with its historic village green, colonial homes, and a laid-back coastal rhythm. Guilford feels both timeless and welcoming — a place where centuries-old clapboard houses and salt marshes blend seamlessly with art galleries, farm markets, and seaside strolls.
From Stonington, I drove about an hour west along the shoreline and spent two days at the historic Whitfield House B&B — a romantic colonial inn with wide plank floors, cozy rooms, and a garden perfect for morning coffee.
I wandered the Guilford Green, one of the largest and most beautiful town greens in New England, surrounded by boutiques, cafés, and antique shops. I toured the Henry Whitfield State Museum, the state’s oldest house, built in 1639 from stone. Afternoons were for coastal walks at Jacobs Beach and exploring the wooded trails at Westwoods, while evenings ended with fresh farm-to-table dining at The Marketplace, where the seasonal berry tart was a highlight!
6. New Britain
This industrious and culturally rich city, known as the “Hardware City” for its manufacturing heritage, surprised me with its mix of proud history, global influences, and an energetic arts scene. New Britain blends working-class grit with vibrant community spirit — from Polish bakeries and colorful murals to world-class museums tucked into tree-lined neighborhoods.
From Guilford, I drove about 45 minutes northwest inland and spent two days at the historic Centennial Inn, a cozy and welcoming inn with Victorian-era details and modern touches.
I toured the New Britain Museum of American Art — the first museum in the country dedicated exclusively to American works — with its sweeping collection of Hudson River School landscapes and bold contemporary pieces. I strolled through Walnut Hill Park, designed by Frederick Law Olmsted, whose rolling lawns and rose gardens were the perfect afternoon escape. I explored the New Britain Industrial Museum for a fascinating glimpse into the city’s manufacturing past, then capped the evenings with authentic Polish comfort food at Staropolska, where the pierogi sampler was unforgettable!
7. New Haven
This vibrant coastal city, best known as the home of Yale University, swept me up with its mix of Ivy League grandeur, artsy energy, and foodie culture. New Haven feels both historic and youthful — a city where Gothic spires rise over tree-lined greens, world-class museums sit beside indie theaters, and every corner café buzzes with student life and creativity.
From New Britain, I drove about 35 minutes south and spent two days at The Study at Yale — a chic, bookish boutique hotel with mid-century style and an unbeatable location near the campus.
I strolled across the New Haven Green, framed by stately churches and historic architecture, before wandering into Yale’s campus with its collegiate Gothic courtyards and secret-feeling libraries. The Yale University Art Gallery and the Yale Center for British Art were both free — and both world-class. In the evening, I joined the debate every visitor must: trying New Haven–style pizza. At Frank Pepe’s, the coal-fired white clam pie was a revelation!
8. Bristol
This lively city, known as the home of ESPN and America’s oldest amusement park, charmed me with its mix of family-friendly fun, cultural treasures, and pockets of small-town New England charm. Bristol feels like a city that celebrates its past — from clockmaking and carousels to cozy neighborhoods — while also buzzing with fresh energy and community pride.
From New Haven, I drove about 45 minutes north and spent two days at the DoubleTree by Hilton in downtown Bristol — a comfortable base with easy access to both history and adventure.
I spent the morning at Lake Compounce, the nation’s oldest continuously operating amusement park, where wooden roller coasters and water rides sit alongside a sparkling lake. I explored the New England Carousel Museum, where ornate carved horses and gilded chariots gleam under soft lights, then wandered through the American Clock & Watch Museum, a nod to Bristol’s heritage as a hub of timepiece manufacturing. Afternoons meant leafy strolls around Rockwell Park, and in the evening I capped it all off with Italian comfort food at San Gennaro’s, where the eggplant parmesan was a highlight!
9. Stamford
This bustling coastal city — the third largest in Connecticut — charmed me with its blend of modern skyline, waterfront parks, and a vibrant arts-and-dining scene. Stamford has the energy of a mini–New York City, yet with the friendliness of a small town and the added bonus of sparkling views over Long Island Sound.
From Bristol, I drove about an hour southwest and spent two days at the Stamford Harbor Hotel — a romantic waterfront spot with sleek rooms and sweeping marina views.
I wandered the Harbor Point district with its trendy restaurants and boardwalks, explored the Stamford Museum & Nature Center (complete with historic barns, farm animals, and woodland trails), and strolled along the breezy paths of Cove Island Park. In the evenings, I dove into Stamford’s food scene — from rooftop cocktails downtown to a cozy Italian dinner at Pellicci’s, where the chicken parm was unforgettable!
Conclusion
Each of these Connecticut towns offered me something different, a pause, a spark, a memory. What they all share is a sense of place you can feel right away. They don’t rush you. They invite you in, let you wander a while, and maybe leave with a little more quiet joy than you came with. Whether you’re craving ocean views, a slice of famous pizza, or a stroll through centuries of history, you’ll find it here, close enough for a day, rich enough to linger in your mind much longer.
Booking Checklist
1. Book Your Flight - I use Expedia because I like their mobile app with my itinerary. They've helped me re-book flights on many occasions. Once you reach their Gold tier, support is especially good.
2. Book Your Hotel - I use Booking.com or Expedia, depending on my destination.
3. Book Your Rental Car - I use Expedia.
4. Book your tours on Viator or Get Your Guide.
