Best Things to Do in Connecticut
Connecticut surprises you with its mix of history, nature, and culture, all tucked into one beautiful corner of New England. When I lived there as a local, I spent many weekends day tripping around the state. Whether you’re after a relaxing coastal escape, a foodie adventure, or a journey into America’s past, you’ll find it here. I know I’ll keep going back, and I hope you discover your own favorite places, too.
1. Downtown 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 — its pretty clapboard houses, charming harbor views, and historic shipyard gave it a magical, timeless quality that felt both authentic and very nostalgic!
Once a bustling seaport, Mystic still proudly celebrates its maritime heritage, with tall ships, working boatyards, and a lively downtown that makes you feel like you’ve stepped into a classic New England storybook.
From New Haven, I took the easy one-hour drive east to Mystic and checked into the cozy Whaler’s Inn right in the heart of downtown. I strolled through the Mystic Seaport Museum — a living history village full of old ships and maritime tales — wandered across the photogenic Bascule Drawbridge, and browsed the quirky boutiques and seaside gift shops that line Main Street. 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? Mystic can feel crowded on summer weekends, especially around the drawbridge. Arriving early in the day or midweek gave me the most relaxed experience.
2. Essex
Essex was one of the most enchanting small towns in Connecticut — its tree-lined streets, white clapboard houses, and pretty marina gave it a timeless New England charm that felt both authentic and nostalgic! Once a thriving shipbuilding center, Essex still proudly celebrates its nautical past, with historic inns, sailing heritage, and a downtown that feels straight out of a classic storybook.
From Mystic, I took the quick 25-minute drive west to Essex and checked into the historic Griswold Inn (famously one of the oldest continuously operating inns in the U.S.!).
I strolled down Main Street with its colonial-era buildings and antique shops, wandered to the harbor to watch boats along the Connecticut River, and popped into the Connecticut River Museum where I learned about the town’s shipbuilding days and even saw an exhibit on the War of 1812. I capped the evening with a cozy dinner back at the inn, complete with hearty seafood chowder and live folk music.
A downside? Essex is small, so evening life quieted quickly. After dinner, there wasn’t much open, but the calm of the streets under lamplight gave it its own charm.
3. New Haven
I thought this lively coastal city, founded in 1638, was one of the most fascinating destinations in Connecticut — its elegant architecture, leafy town greens, and mix of history and culture gave it an atmosphere that felt both intellectual and warmly nostalgic! Known as the home of Yale University, New Haven still proudly celebrates its heritage with world-class museums, iconic Gothic-style buildings, and a food scene that rivals much larger cities.
From Essex, I took the quick 40-minute drive west to New Haven and checked into the boutique Graduate Hotel, located right in the heart of Yale’s campus. I wandered across the historic Yale Old Campus, admired the soaring towers of Harkness Hall, and spent hours exploring the Yale University Art Gallery, Ely Center of Contemporary Art (free, $85 for events), and the Peabody Museum of Natural History. Of course, I had to sample New Haven’s legendary pizza — locals swear by the thin, coal-fired pies at Frank Pepe Pizzeria Napoletana, and I couldn’t agree more. Later, I strolled through the picturesque New Haven Green and capped the evening with a concert at the Shubert Theater.
4. Stonington, CT
I took a break in this historic seaside town during this month and found the weather was warm and dry (with a refreshing breeze off the water and occasional misty mornings) and just perfect for exploring the charming coastal landscapes. The harbors were alive with sailboats, gardens were blooming with colorful summer flowers, and the whole community buzzed with seasonal festivals, farmers markets, and open-air concerts.
I visited the celebrated Stonington Village Fair on the town green, the Summer Music Festival that featured local and regional performers, and caught a play at the intimate Stonington Opera House, which was buzzing with summer productions.
I flew into Providence, drove just under an hour, and settled in for five days at The Inn At Stonington of shoreline adventures—kayaking through the calm waters of Stonington Harbor, strolling the scenic Bluff Point State Park trails, and soaking up the nautical charm of downtown Stonington Borough with its antique shops, art galleries, and beloved seafood shacks.
5. Stratford
Stratford is a classic New England riverside town where the weather pleasantly warm and sunny in August, with just the occasional breezy afternoon drifting in from Long Island Sound. It was perfect for strolling through historic neighborhoods, exploring the shoreline parks, and enjoying the town’s strong ties to arts and theater. Summer flowers brightened the town green, and there was a lively energy with concerts, fairs, and farmers markets in full swing.
I attended the world-famous Shakespeare Festival Theater season (a Stratford tradition dating back to the 1950s), caught an open-air concert at Short Beach Park, and explored the exhibits at the National Helicopter Museum, which highlights Stratford’s unique aviation history as home to Sikorsky Aircraft.
I flew into Bridgeport/Igor I. Sikorsky Memorial Airport—right in Stratford itself!—and settled in 3-star The Surfside Hotel for five days of shoreline adventures: kayaking along the Housatonic River, birdwatching in the scenic Roosevelt Forest, and soaking up the charm of Main Street with its independent coffee shops, art venues, and locally loved restaurants.
6. New Milford
I took a break in this charming small town during this month and found the weather warm and clear, with crisp evenings that were perfect for enjoying outdoor dining or a summer concert on the green. The rolling hillsides and surrounding farms were alive with color, and the town had a welcoming, down-to-earth vibe with farmers markets, community festivals, and open-air art events filling the calendar.
I caught live music at Harrybrooke Park, a peaceful estate-turned-community park with sweeping lawns and woodland trails.
I drove in from New York City (just under two hours) and settled in for five days of countryside exploration at The Rocky River Inn —kayaking along the Housatonic River, hiking the scenic Lovers Leap State Park trails, and soaking up the charm of Bank Street with its historic storefronts, local galleries, and family-run cafés.
7. Charles W. Morgan
Charles W. Morgan, beautifully preserved at Mystic Seaport Museum, felt alive with history and the energy of visitors exploring its decks and surrounding exhibits. The harbor was dotted with sailboats, and the museum grounds were buzzing with demonstrations, artisan shops, and festivals celebrating maritime traditions.
I joined a fascinating living history tour of the Morgan, explored hands-on exhibits about New England’s whaling past, and even watched a traditional boatbuilding demonstration in the working shipyard nearby. Families picnicked along the waterfront, while music from a sea shanty performance carried across the wharves.
I drove into Mystic (a little over an hour from both Providence) and spent the day wandering between the ship, the recreated 19th-century seafaring village, and the lively town of Mystic itself—famous for its charming shops, harborside restaurants, and of course, Mystic Pizza.
8. Bridgeport
Bridgeport had a vibrant summertime energy—local parks filled with music, families enjoying the shoreline, and a steady rhythm of festivals, art shows, and farmers markets.
I explored the Barnum Festival (a colorful tradition celebrating P.T. Barnum’s legacy with parades, concerts, and fireworks), strolled the paths of the Connecticut’s Beardsley Zoo, and enjoyed an outdoor concert at Seaside Park, a sweeping waterfront green space designed by Frederick Law Olmsted, the same landscape architect behind Central Park.
I flew into Sikorsky Memorial Airport in nearby Stratford and settled in for two days of urban and shoreline discovery at Best Western Plus Fairfield Hotel —kayaking along Black Rock Harbor, browsing the galleries at the Housatonic Museum of Art, and soaking up the eclectic vibe of downtown Bridgeport with its indie coffee shops, performance spaces, and buzzing dining scene.
Conclusion
Connecticut always surprised me with its contrasts. One moment I was walking the deck of a 19th-century whaling ship, the next I was floating past riverbanks on a vintage train or chasing coaster screams under cotton candy clouds. Art lived in quiet gardens, stories echoed through hangars and historic homes, and the coast whispered secrets in every salty breeze. What I found wasn’t just a small state with old charm, it was a place where history and happiness exist side by side, always inviting you to stay a little 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.
5. If you are planning to visit more than three national parks in the next 12 months, buy the America the Beautiful Pass.
