Best Places to Visit in Connecticut

Searching for the best places to visit in Connecticut? Well, you are in the right place! I've traveled all around "The Constitution State" while living on the East Coast for ten years and I've always loved it. For a small state, it holds such variety I explored on my recent four week road trip. I’ve narrowed it down to the places that left the biggest impression on me and I hope you'll love it too.

Best Places to Visit in the Lower Connecticut River Valley

I think this is one of the state’s most scenic and historic regions and one of my favorite places to visit!

1. Essex

This was one of the most enchanting small towns in Connecticut and it quickly became one of my favorite Connecticut day trips (just 2 hours from NYC)!

We stayed at the historic 3-star Griswold Inn for two days (famously one of the oldest continuously operating inns in the U.S.!) for two days which was super cool.

We started in the historic village, which to me felt timeless with its colonial-era buildings. My favorite part was walking along Main Street together with Chris and our son.

We stopped for lunch at Noah's at 63 Main, a cozy riverside restaurant. Fresh seafood was perfect for us, especially with the water right beside us.

In the afternoon, we explored the nearby Connecticut River Museum ($15 for adults, $5 for kids), great if you are a history buff like me. I loved learning how connected the Essex is to the water.

What I loved best:

I capped the evening with a cozy dinner back at Griswold Inn where we were staying. The hearty seafood chowder really hit the spot, my favorite highlight.

A downside? The town itself is pretty small, so evening life quieted quickly. After dinner, there wasn’t much open. Coming from NYC, it was perfect and helped us relax, but I just thought I'd mention it!

2. Gillette Castle

I thought this is one of the most beautifully unspoiled and dramatic viewpoints in Connecticut, just 10 minutes by car from Essex, so it's a perfect side trip.

The first thing we did was walk around the outside, and the castle itself looked like something straight out of a dream.

After, going inside was my favorite part of the experience, since the rooms were so interesting, quirky, and honestly one of the coolest designs I’ve ever seen.

We wandered through narrow staircases, secret doors, and strange wooden locks, and it felt like a brilliant idea turned into a real-life fairytale adventure.

The castle is located in Gillette Castle State Park, which made it even better because after touring inside, we explored the grounds and enjoyed the most amazing river views.

What I loved best:

What made it exceptional to us was learning about William Gillette himself, whose creative mind made this place feel truly unique and personal, my favorite highlight. We were all very inspired by this place on our family vacation to Connecticut, and on top of that it was very educational for our son!

3. Old Saybrook

Chris and I both absolutely love Old Saybrook, and have been many times. We drove up from about our apartment in NYC (about 2 hours by car!). I think Old Saybrook is one of the most beautifully unspoiled stretches of shoreline I’ve explored in New England,.

Whether you are here for a day or a week, I recommend starting near the water, for the views alone. We admired sailboats drifting by for a while before heading downtown.

Downtown Old Saybrook is lovely with quaint streets, locally owned boutiques, and cafés. We stopped for lunch at Fresh Salt right on the water and had amazing fresh seafood!

A highlight was learning about Old Saybrook’s history and its connection to Katharine Hepburn.

What I loved best:

In the evening, I had fresh seafood at Liv’s Oyster Bar with a tasty lobster roll, my favorite highlight.

A downside?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.

Best Places to Visit in Eastern Connecticut

This region is rich in New England character without the crowds.

4. Stonington

This small village in southeastern Connecticut is one of my favorite places to visit on the East Coast when I'm in the mood for waterfront dining, and historic sites. Chris and I had an amazing romantic two-day stay at Inn at Stonington, a cozy waterfront inn for our anniversary.

We started our morning wandering through Stonington Borough, and found ocean views incredibly romantic!

After lunch at Dock 9, my favorite part of the day was walking along Stonington Point, watching as waves crashed softly against the rocks and admired the New England lighthouse.

I loved exploring the town’s maritime history, especially the quiet corners near the old fishing docks, which gave us plenty to talk about as we walked and explored together.

What I loved best:

Our anniversary dinner at Noah’s Restaurant which serves Portuguese-inspired seafood was my favorite highlight. The restaurant dates back to the 70s and made me picture what life in this historic village was like back then.

5. Things to Do in Mystic - 2 hours from Boston or NYC

I thought this picturesque waterfront town, founded in the 1600s, was one of the most enchanting spots in coastal Connecticut! From New Haven, I took the easy one-hour drive east to Mystic and checked into the cozy Whaler’s Inn (from $312/night) for two days right in the heart of downtown.

First, I strolled through the Mystic Seaport Museum, full of old ships and incredibly interesting. Then, I wandered across the photogenic Bascule Drawbridge, and finally enjoyed the Main Street.

What I loved best:

I couldn’t resist stopping at the legendary Mystic Pizza (made famous by the Julia Roberts film!) and later ended the day with a peaceful sunset walk along the Mystic River.

A downside? The town can feel crowded on summer weekends, especially around the drawbridge. Arriving early in the day or midweek gave me the most relaxed experience.

Best Places to Visit in Central Connecticut

This region offers a mix of history, arts, and natural beauty.

6. New Haven

This cool coastal city is the home of Yale University, and it completely won me over with its artsy energy, and foodie culture! We spent two days at The Study at Yale, a chic, bookish boutique hotel with mid-century style and an unbeatable location near the campus.

We started our morning wandering through the Yale University campus, where we admired Gothic architecture. My favorite part of the day was strolling through the Yale University Art Gallery right after.

From there, we made our way through downtown New Haven. Ely Center of Contemporary Art was one of my favorite spots.

Later in the afternoon, we headed toward East Rock Park, with panoramas of the city, the harbor, and the distant shoreline, for me, absolutely worth the climb.

In the evening, we had New Haven–style pizza at Frank Pepe’s (the coal-fired white clam pie was a revelation!).

What I loved best:

Our meal at Olea which serves an innovative interpretation of Spanish and Mediterranean cuisine downtown was my favorite highlight.

7. Hammonasset Beach

Stretching for nearly two miles along Long Island Sound, this is a beach lovers paradise and one of my favorite places to visit in Connecticut when I'm craving sand and ocean. Yes, it's busy on summer weekends but go any other time and you can find a peaceful stretch to call your own. First, we enjoyed strolling along the boardwalk that traces the edge of the dunes.

Later, we explored Meigs Point Nature Center, learning about local wildlife and coastal ecosystems, which made the landscape around us feel even more special and alive.

What I loved best:

In the afternoon, we laid out a blanket back at the beach, sharing snacks and watching sailboats, my favorite highlight.

Best Places to Visit in South Central / Coastal Connecticut

I love the way South Central Connecticut pairs historic coastal cities with classic shoreline scenery.

8. Wadsworth Falls State Park

Just 35 minutes from Hammonasset Beach, this is one of the most beautifully unspoiled natural parks I’ve ever visited in Connecticut.

I love that Wadsworth Falls State Park offers miles of trails, emerald pools, and two stunning waterfalls! I thought it was pure, refreshing nature at its best and it quickly became one of our favorite day trips from NYC.

What I loved best:

Wadsworth Falls felt like a place where time slowed a bit, just for a day, a real standout.

9. Hartford

Ahh Hartford, Connecticut, a small city with a surprisingly big place in American history. Often overshadowed by nearby Boston and New York, Hartford is actually one of the oldest cities in the United States and a fantastic destination if you are like me and love literature, architecture, and early American history. If you’ve never been, Hartford has a quiet charm that’s hard to appreciate until you explore it firsthand.

The absolute highlight and where we started is the Mark Twain House, where Twain wrote some of his most famous works, including The Adventures of Tom Sawyer and Adventures of Huckleberry Finn.

Next, we explored Bushnell Park, the oldest publicly funded park in the U.S. on a sunny day. After lunch, we enjoyed visiting the Wadsworth Atheneum Museum of Art, the oldest public art museum in the country!

Hartford is about 2 hours from New York City, making it an easy weekend getaway. If you have a car, the drive is straightforward with minimal tolls. There’s also an Amtrak train that runs directly from NYC.

Once you’re there, most major attractions are close enough to explore on foot or with short rides. For travelers who want a deeper understanding of Hartford’s role in American history, I think that a guided tour is well worth it and will probably save you a lot of time.

What I loved best:

My personal highlight was modern Italian comfort food at Salute, where the butternut squash ravioli was a true highlight!

Best Day Trips in Western Connecticut

This region includes upscale coastal towns, scenic countryside, and some of the state’s most impressive natural landscapes.

10. Milford

Ready for a breezy shoreline escape? Check out Milford, a real standout! This was one of the most unexpectedly charming coastal towns in Connecticut!

From Mystic, I took the easy drive southwest to Milford and checked into a cozy vacation rental near the town green for six days — the perfect base for exploring both its beaches and its countryside corners.

First, I wandered through Milford’s welcoming downtown, full of cute cafés and small shops, then made my way towards the water, where the boardwalk led me straight into Silver Sands State Park where we spent most of our days just relaxing.

What I loved best:

Walking on the low-tide sandbar out toward Charles Island was my personal highlight.

A downside? This place is peaceful after dark, and once the dinner crowd fades, things quiet down quickly.

11. Bridgeport Activities and Attractions

There’s something about this city that instantly made me feel like I’d uncovered a coastal hidden gem!.

After just 1 hour and 30 minutes by car from NYC, we first enjoyed the Barnum Festival (a colorful tradition celebrating P.T. Barnum’s legacy with parades, concerts, and fireworks). Next, we strolled along the paths of the Connecticut’s Beardsley Zoo which my son loved.

Finally, we enjoyed an outdoor concert at Seaside Park, a sweeping waterfront green space designed by Frederick Law Olmsted (the same landscape architect behind Central Park!).

We turned the day trip into a weekend and spent two days at Best Western Plus Fairfield Hotel.

What I loved best:

In the evening, I made my way to Walrus Alley, the lively, brick-lined restaurant tucked just off Post Road East in Westport, CT (20 minutes by car). Their smoked meats, creative small plates, and warm, bustling atmosphere made it an instant favorite — the kind of place you immediately want to return to.

12. Enders Falls

This series of waterfalls is one of the most unspoiled and breathtaking natural areas I’ve visited in Connecticut, and I think it’s one of the absolute best waterfall hikes in the state!

The falls are surrounded by forests and consist of a series of waterfalls and tranquil pools carved into a wild gorge.

After a winding drive through the small town of Granby, I arrived at Enders State Forest. A short hike down a woodland trail brought me to the sound of rushing water.

What I loved best:

Each turn in the path unveiled a new waterfall which was super cool!

13. Kent Falls

Ready for a dramatic mountain-side escape? Check out Kent Falls, a real standout! In the northwestern corner of Connecticut, you'll find my favorite waterfall that drops 250 feet in a dramatic series of cascades. Often called the “jewel of the Litchfield Hills,” Kent Falls State Park is a highlight of any New England road trip.

What I loved best:

It's especially stunning during fall foliage weekends in late September / early October around Columbus Day!

14. Things to Do in Stratford

This town, set where the Housatonic River meets the Sound, is one of my favorite places to visit in Connecticut when I want a mix of nature, food, and waterfront adventure.

Our purpose for this trip was to attend the world-famous Shakespeare Festival Theater season (a Stratford tradition dating back to the 1950s), and caught an open-air concert at Short Beach Park. We spent two days at the 3-star Surfside Hotel.

What I loved best:

Exploring the exhibits at the National Helicopter Museum, which highlights Stratford’s unique aviation history as home to Sikorsky Aircraft was my favorite highlight.

15. Stamford

This bustling coastal city (the third largest in Connecticut!) wowed me with its modern skyline, waterfront parks, and a vibrant arts-and-dining scene. Stamford has the energy of a mini–New York, yet with the friendliness of a small town and the added bonus of 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.

First thing we did was walk around downtown Stamford, and the vibrant energy mixed with modern buildings and historic corners was such a cool experience.

After, we explored the waterfront area which honestly felt like magic with boats, cafes, and sparkling views everywhere. Walking along the Harbor Point boardwalk was one of my favorite moments.

Next we headed to Mill River Park, right in the heart of the city, and it was such a hidden green gem surrounded by the skyline. The park was full of families, runners, and people just enjoying life, making it one of the best experiences for a relaxing afternoon.

For lunch we grabbed food nearby at one of the most interesting local spots, and it was affordable but still absolutely delicious.

As the sun went down, dinner by the water was spectacular and honestly one of the best meals we had, with views that made the night feel special.

The next morning we visited Cove Island Park, just minutes from downtown. Walking the trails and watching the waves was such an underrated and calming experience.

What I loved best:

Cozy Italian dinner at Pellicci's was a standout, where the chicken parm was unforgettable!

16. Things to Do in New Milford

I think this one of the best countryside escapes in the region! I drove on from New York City (just under two hours) and settled in for five days of countryside exploration at The Rocky River Inn. During our mini-vacation, we enjoyed hiking along Lovers Leap State Park trails, strolled on Bank Street with its historic storefronts, local galleries, and local cafés.

One day, we headed to Harris Hill Farm, a family-run spot that felt like stepping into a quiet slice of rural Connecticut. Surrounded by rolling fields, barns, and fresh country air, it was warm, and down-to-earth. Whether you’re sampling seasonal treats or just taking in the pastoral scenery, it’s one of those “hidden gem” experiences that makes Milford feel so special.

What I loved best:

We caught live music at Harrybrooke Park, a peaceful estate-turned-community park, a personal highlight.

17. Greenwich

Often called the “First Town in America”, this place charms me every time we visit. This month, we stayed two days at 4-star Delamar Greenwich Harbor, a AAA 4-Diamond hotel so you can trust that it's high quality.

After arriving, we headed straight to Greenwich Avenue, which is the most vibrant area and honestly one of my favorite streets to walk.

We grabbed coffee at a small café nearby and it was such a joyful and affordable start to the day, simple but amazing.

Next, we went down toward Greenwich Harbor, which is close to Long Island Sound, and the views were absolutely spectacular. Walking along the water felt like magic, boats everywhere, fresh air, and that calm coastal vibe that makes this place underrated.

Later on we explored Binney Park, which was one of the best surprises and a brilliant idea for a relaxing break. The park felt peaceful and romantic, with bridges, ponds, and paths that made it perfect for family or couples.

After that, lunch was near downtown again and we picked a casual spot that ended up being an awesome experience.

In the afternoon, we visited the Bruce Museum which was a unique and unusual mix of art and science.

What I loved best:

For me, Greenwich is one of the best places to visit in Connecticut because it's peaceful, affordable, and hope you will love it too!

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. Metro-North Railroad is the better option if you are coming from NYC.

Hi, I'm Ema. I'm the face behind VacationIdea.com. What started as a simple travel blog for regular people who love to travel like us evolved into a 30-year life-long endeavor - VacationIdea.com. I live in Texas with my husband and son. More about us.