Best Places to Visit in Connecticut
As a local, I traveled all around Connecticut all the time 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”) charms me everytime I visit. It's a small city with historic architecture and its iconic views over the Long Island Sound. With its colonial heritage, elegant homes, lively downtown, and being close enough to New York City to commute, I can 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 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!
- Location: Map & Directions
Parking near the Avenue on weekends was tricky. I circled longer than I wanted before finding a spot. Metro-North Railroad is the better option if you are coming from NYC.
2. Hartford
This historic New England capital (often called the “Insurance Capital of the World”) has a mix of old-world charm and modern energy, a city where historic homes and cultural landmarks meet a lively downtown and riverside parks.
From Greenwich, I drove about an hour and twenty minutes north and spent two days in Hartford at the elegant 3.5 star Goodwin Hotel.
You can tour the Mark Twain House & Museum and step next door into the Harriet Beecher Stowe Center to learn about the writer’s abolitionist legacy. I strolled through Bushnell Park admiring its Gothic Soldiers & Sailors Memorial Arch, and explored 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!
- Location: Map & Directions
3. Old Saybrook
This coastal gem and one of Connecticut’s oldest instantly won me over with its historic charm, seaside air, and relaxed New England vibe. Old Saybrook has a kind of timeless grace: tree-lined streets, antique homes, and the legachy 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.
You can check out Main Street’s boutiques, tour the General William Hart House, and visit the Katharine Hepburn Cultural Arts Center. My afternoons were spent walking the boardwalks of Harvey’s Beach, dipping into antique shops, and savoring the salty breeze along the causeways. In the evening, I had fresh seafood at Liv’s Oyster Bar with a tasty lobster roll.
- Location: Map & Directions
Expect parking near the beach to be limited. I spent more time looping through side streets than I wanted before finally settling in to enjoy the sand.
4. Stonington
This historic New England seaside village at the state’s southeastern tip felt like stepping into a postcard with a charming blend of salt air, colonial-era homes, and cobblestone streets. With its working harbor, vineyards along the countryside, and colorful 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.
I checked out Water Street’s boutiques, cafés, and 18th-century homes, explored the Old Lighthouse Museum, and took lots of walks. You can also head to Saltwater Farm Vineyard (a converted WWII airplane hangar turned vineyard), and eat dinner at Noah’s Restaurant which serves Portuguese-inspired seafood. The restaurant dates back to the 70s and made me picture what life in this historic village was like back then.
- Location: Map & Directions
5. Guilford
Guilford has a cool historic village green, colonial homes close to the Atlantic shore. You'll see centuries-old clapboard houses here, yes, but also modern art galleries and farm markets.
I only spend an afternoon here so I'm not an expert. You can walk around the Guilford Green, check out the boutiques, cafés, and antique shops. There's also the Henry Whitfield State Museum, the state’s oldest house, built in 1639 from stone! Jacobs Beach was a highlight though it was too cold to swim in November. You can also check out the wooded trails at Westwoods, and have a super affordable farm-to-table meal at The Marketplace, where the seasonal berry tart was a highlight!
- Location: Map & Directions
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!
- Location: Map & Directions
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!
- Location: Map & Directions
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!
- Location: Map & Directions
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 4-star DoubleTree by Hilton Stamford, a romantic waterfront spot with sleek rooms and sweeping marina views.
You can walk around the Harbor Point district with its trendy restaurants and boardwalks, explore the Stamford Museum & Nature Center (complete with historic barns, farm animals, and woodland trails), and stroll along the breezy paths of Cove Island Park. In the evenings, I dove in Stamford’s food scene — from rooftop cocktails downtown to a cozy Italian dinner at Pellicci’s, where the chicken parm was unforgettable!
- Location: Map & Directions
10. Silver Sands State Park, Milford
This coastal sanctuary was absolutely beautiful, with its sweeping tidal marshes, quiet sandy beaches, and a breezy boardwalk that stretched elegantly between dunes and sea grasses.
After an easy 15-minute drive from downtown Milford, we arrived at a park that seemed to breathe calm and light—where gulls wheeled overhead, the tide whispered along the shore, and the horizon stretched wide and endless across Long Island Sound.
You can stroll along the raised wooden boardwalk connecting Silver Sands to Walnut Beach, admire the shifting colors of the marshlands, spot herons and egrets, and walk on the low-tide sandbar out toward Charles Island.
11. Wadsworth Falls State Park
I thought this woodland retreat was absolutely enchanting when I visited this month. I loved with its forested trails, rushing cascades, and tranquil river bends tucked quietly into the heart of Connecticut. Known for its pair of waterfalls—one bold and dramatic, the other gentle and picturesque, Wadsworth Falls felt like a place where time slowed a bit, just for a day.
- Location: Map & Directions
- Wadsworth Falls website
12. Gillette Castle
I loved my day trip to this eccentric medieval-style fortress perched high on a bluff above the Connecticut River. This is where William Gillette, the actor famous for portraying Sherlock Holmes, had once lived out his creative vision in stone.
You can tour the castle’s quirky interior, with its hand-carved wooden doors, intricate locks, and hidden spy windows. Outside, there is a park that feels a little bit mysterious and very relaxing.
- Location: Map & Directions
- Gillette Castle website
13. Enders Falls
Surrounded by forests of north-central Connecticut, Enders Falls is a series of plunging waterfalls and tranquil pools carved into a wild, rocky gorge.
After a winding drive through the small town of Granby, I arrived at Enders State Forest, where a short hike down a woodland trail brought me to the sound of rushing water echoing through the trees. Each turn in the path unveiled a new waterfall. I like to linger at the largest falls which feels the most mysterious to me, where the cascade thundered over mossy rocks into a deep emerald pool.
- Location: Map & Directions
- Enders Falls website
14. Kent Falls
In the northwestern corner of Connecticut, you'll find my favorite waterfall, Kent Falls that drops 250 feet in a dramatic series of cascades. Often called the “jewel of the Litchfield Hills,” the park is a highlight of any New England road trip. It's especially stunning during fall foliage weekends in late September / early October around Columbus Day!
- Location: Map & Directions
- Kent Falls website
15. Mystic Seaport
Last but not least is Mystic Seaport. People don't know this about me but I used to spend two weeks at a time here when I was a child. The town brings back good memories. With tall ships moored in the harbor, costumed interpreters, and the salty breeze, the entire village is a living musem into 19th-century life along New England’s coast.
You can tour the Charles W. Morgan (the last wooden whaling ship), check out the seaport village with its cooper shop, schoolhouse, and general store, and visit the Mystic Seaport Museum. A sunset walk along the riverfront is a must to end your day! The Whaler's Inn Hotel of Mystic and Delamar Mystic are both great for a weekend getaway.
- Location: Map & Directions
16. Hammonasset Beach
Stretching for nearly two miles along Long Island Sound, Hammonasset Beach is a beach lovers paradise. Yes, it's busy on summer weekends but go any other time and you can find a peaceful stretch to call your own. You can strool along the boardwalk that traces the edge of the dunes, check out the Meigs Point Nature Center, watch a stunning sunset here!
- Location: Map & Directions
- Hammonasset Beach website
Conclusion
Each of these Connecticut places offered me something different, a pause, a spark, a memory. What they all share is a sense of place you can feel right away.
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.
