20 Adorable Towns and Cities in Connecticut You Won’t Want to Miss!

The perfect embodiment of New England charm and coastal chic, Connecticut is a fascinating Northeast state home to several quaint coastal towns, Fortune 500 companies and cosmopolitan cities. Sandwiched between Massachusetts, New York and Rhode Island, Connecticut is among the oldest states in the nation and is known as the Constitution State, with less than 60 miles (96 km) separating Connecticut from Boston and New York City. From the charming downtown district of Hartford to the streets of Bridgeport, Connecticut’s university cities to cities with some of New England’s best restaurants and stunning beaches, here are the best cities in Connecticut to visit.

20 Connecticut Cities And Towns

Cities In Connecticut

1- Hartford

The capital city of Connecticut and the former home of author Mark Twain, Hartford is a history-packed, culturally vibrant New England city in the heart of the Constitution State.

With a population of more than 120,000 residents, Hartford is among the largest cities in Connecticut and one of the oldest in the United States, founded in 1635.

Hartford has some of the best landmarks, museums and public parks in the northeast and is known as the “Insurance Capital of the World” due to the many financial and insurance companies headquartered there. 

Things to do in Hartford include stopping by the Connecticut State Capitol, touring the Mark Twain House & Museum and exploring the Wadsworth Atheneum Museum of Art.

Recommended tour: Hartford Scavenger Hunt: The Riches Of Hartford

Stay at: Delamar West Hartford

2- Stamford

Renowned for its excellent dining and shopping options, a plethora of Fortune 500 companies, and proximity to New York City, Stamford is a cosmopolitan city in Connecticut. 

Stamford is just 40 miles (64 km) from the Big Apple and was first settled in 1641, making it one of the oldest cities in the United States.

The city forms part of the broader New York City Metropolitan Area.

It is home to UConn Stamford and the Norwalk Community College campuses, giving it a lively and multicultural identity.

Stamford treats travellers to various attractions, including the Stamford Museum & Nature Center, Cove Island and the Bartlett Arboretum & Gardens.

Recommended tour: Adventurous Scavenger Hunt in Stamford by Zombie Scavengers

Stay at: Luxury Apartments by Hyatus at The Asher

3- New Haven

The third-largest city in all of Connecticut, New Haven is a world-class educational hub best known for being home to the main campus of the prestigious Yale University, the third-oldest university in the United States.

New Haven was first platted and settled back in 1638 by English Puritans, making it one of the very first planned cities in the United States.

The city is famous for its historic “Nine Square Plan”, a 4-by-4 street grid laid out a year after the city’s settlement that has some of New Haven’s oldest architecture.

Steeped in New England culture and tradition, New Haven is a history buff’s dream destination, with venues such as the Yale Peabody Museum, the Yale Center for British Art and the New Haven Green to visit.

Recommended tours:

• New Haven’s Ghost Walk
• New Haven Scavenger Hunt: Yale & Beyond

Stay at: Luxury Furnished Apartments by Hyatus Downtown at Yale

4- Bristol

In Connecticut’s central region, about 20 miles (32 km) southwest of the Constitution State’s capital, Bristol is a cultured and down-to-earth mid-sized city.

This city in Connecticut is home to Lake Compounce Amusement & Water Park, the oldest continuously operating amusement park in the United States.

Lake Compounce opened in 1846, however, it’s not the only major attraction Bristol is known for, as this low-key New England city also serves as the headquarters of sports broadcasting giant ESPN.

Bristol’s other attractions are the Carousel Museum and the Harry C Barnes Memorial Nature Center.

Stay at: Home2 Suites By Hilton Bristol

5- Norwalk

Home to a range of shops and restaurants, Norwalk is renowned for its ties to the oyster industry, earning Norwalk the nickname “Oyster Town”.

The city is home to about 90,000 residents, enough to claim the title of Connecticut’s sixth-largest, and was officially established in 1649.

Named after the Algonquin word “noyank”, Norwalk has several attractions, ranging from the stately Lockwood-Mathews Mansion Museum to the fascinating Maritime Museum. 

Stay at: Delamar Greenwich Harbor

6- Bridgeport

Connecticut’s most populated independent city, Bridgeport, is home to the campuses of no four colleges and universities and is also the site of the Constitution State’s only zoo.

Nicknamed “Park City”, Bridgeport is an outdoor enthusiast’s dream destination, with 35 unique public parks covering an area of more than 1,300 acres (14 ha) for visitors to reconnect with nature.

Since the city’s permanent settlement began in 1644, Bridgeport has been the setting for several impressive 20th-century “firsts”.

The first dental hygiene school and Subway restaurant were first opened in Bridgeport, while the city was where the first electric plug outlet was invented. 

From the Barnum Museum and Connecticut’s Beardsley Zoo to the Bijou Theatre and scenic Seaside Park, Bridgeport is a hub worth stopping by along Connecticut’s southwestern coastline.

Recommended tour: Bridgeport Scavenger Hunt: Connecticut’s Biggest Sights

Stay at: Black Rock Home

7- Waterbury

Nicknamed the “Brass City”, Waterbury is a modestly-sized city once the centre of the American brass industry.

Before WWII, some 50,000 brass workers were employed in Waterbury during the city’s brass-production peak.

The 5th-most populated city in Connecticut, Waterbury was officially incorporated as a town in 1686 and as an independent city almost 200 years later in 1853, and became an industrial hub during the start of the 19th century.

Although most of Waterbury’s once thriving brass industry has all but vanished, the city remains a popular destination thanks to attractions such as the Mattatuck Museum, the Palace Theater and the 18-acre (7 ha) Holy Land USA.

Stay at: The Mayflower Inn & Spa

8- Norwich

Officially incorporated in 1784 and affectionately known as “The Rose of New England”, Norwich is a Connecticut city renowned for its scenic rolling hills and old-world charm.

The city is situated in the Constitution State’s southeast corner.

It is within a 50-mile (80 km) drive from downtown Providence, Rhode Island, making Norwich the ideal destination from which to explore some of New England’s most fascinating states.

Visit the Slater Memorial Museum, scenic Mohegan Park and Norwich Arts Center.

Stay at: Villa Signor

9- Meriden

Located roughly halfway between New Haven and Hartford, Meriden is an outdoor enthusiast’s dream destination and home to one of New England’s best Trap Rock Ridges.

These Trap Rock Ridges are natural wonders formed by volcanic activity millions of years ago, with a geological composition predominantly of basaltic trap rock.

The striking landscape offers outdoor opportunities and is a wonder to explore, attracting hikers, nature enthusiasts and geologists.

The city has a population of more than 60,000 residents and over 3,000 acres (1,214 ha) of combined public park space to explore on a sunny afternoon.

Explore the 1,800-acre (728 ha) Hubbard Park, the Augusta Curtis Cultural Center and Gallery 53.

Stay at: Fashionably cozy place

10- New Britain

The city of New Britain in Connecticut’s central region is a New England arts and culture hub nine miles (14 km) outside downtown Hartford.

New Britain was nicknamed “Hardware City” due to being home to the headquarters of both Stanley and Black & Decker and is home to one of the largest Polish-decent populations in the Constitution State.

Attractions range from the world-class New Britain Museum of American Art to the popular Walnut Hill Park, designed by the same landscape architect who designed Central Park in New York City, Frederick Law Olmsted.

Stay at: Grammy’s Lake House

11- Danbury

Located within a 70-mile (112 km) drive from Manhattan, Danbury was once the epicentre of the USA’s hat manufacturing industry, earning Danbury the nickname “Hat City” during the late 19th and early 20th centuries.

Danbury regularly ranks among the best cities to live in the United States and is home to the Western Connecticut State University and the upscale Danbury Fair Mall.

Other attractions include the  Danbury Railway Museum, Tarrywile Park and the Thrillz High Flying Adventure Park.

Stay at: Candlewood Lake -Family Getaway

12- Torrington

The largest city in northwest Connecticut’s Litchfield County, Torrington, is the birthplace of famous abolitionist John Brown, known for his radical activism advocating for the end of slavery in the United States. 

It forms the centrepiece of one of the largest micropolitan areas in the United States.

Torrington is within 80 miles (128 km) from destinations such as New York City, Albany and Springfield, Massachusetts, and was initially settled by Ebenezer Lyman, Jr. in 1735.

Litchfield County’s most populated city is great for families; attractions include the Warner Theatre and the KidsPlay Children’s Museum.

Stay at: The Litchfield Inn

13- Middletown

Home to the leafy campus of Wesleyan University, the college city of Middletown is the most populated in the state’s Lower Connecticut River Valley Planning Region.

Founded by English settlers in 1650, Middletown hosts one of Connecticut’s largest annual pride parades.

It’s renowned for its thriving arts scene, making it one of the most exciting cities in central Connecticut outside Hartford.

Thanks to the city’s scenic riverfront location and rich history, Middletown has natural attractions and exciting cultural venues, such as the Wadsworth Falls State Park, Harbor Park and the General Mansfield House.

Stay at: Private Apt In Middletown-wesleyan

14- West Haven

Only officially incorporated as an independent city in 1961, the young city of West Haven is affectionately known as “Connecticut’s Youngest City” and is home to Yale University’s West Campus.

Despite its recent incorporation, West Haven is among the oldest settlements in Connecticut and was the setting of the now-defunct “Savin Rock Amusement Park”, Connecticut’s premier amusement park during the 19th and 20th centuries.

West Haven provides visitors access to the excellent attractions, shopping and dining options of nearby New Haven, and a couple of local tourist favourites such as the PEZ Visitor Center and the West Haven Veterans Museum.

Stay at: Beachy Bay Breeze Bungalow

15- New London

The seaside city of New London is a southern Connecticut destination jam-packed with history and culture that was once home to the second-largest port in New England during the 1800s.

Modern-day New London is best known for its charming Main Street, which forms part of the National Trust for Historic Preservation’s “Main Street America” program.

This idyllic coastal destination is home to many interesting places to explore, such as the Fort Trumbull State Park and Museum, the Lyman Allyn Art Museum and the Garde Arts Center.

Stay at: New London Hideaway

16- Milford

Perched along the shores of the Long Island Sound in southern Connecticut, Milford is a scenic and outdoor-centred mid-sized city in Connecticut that’s among the oldest permanent settlements in the state.

Founded in 1639, Milford became a shipbuilding and fishing hub during the 18th and 19th centuries.

The city’s booming leather industry made Milford famous for its boots, hats and shoes during the 20th century.

Swing by the Silver Sands State Park, the Robert Treat Farm, the Great River Golf Club and Eisenhower Park to get the most out of your visit to Milford.

Stay at: Beach Apt In Woodmontmilford

Towns In Connecticut

17- Greenwich

Pretty and posh Greenwich in the Constitution State’s southwestern region is the most populated town along Connecticut’s Gold Coast.

Greenwich is within a 34-mile (54 km) drive from downtown NYC.

Although not technically classified as a city, Greenwich is among the largest urban centres in Connecticut and was officially settled by English Puritans in 1640.

Greenwich has a rich maritime past and is a major hub for the arts along the Long Island Sound, treating visitors to stunning nature trails and glimpses of the iconic New York skyline off in the distance.

Greenwich’s most-visited attractions include the Bruce Museum, the Greenwich Audubon Center, the Greenwich Polo Club and Greenwich Point Park.

Stay at: Stanton House Inn

18- Glastonbury

In central Connecticut’s Hartford County less than 10 miles (16 km) from the Constitution State’s capital city, Glastonbury is a mid-sized New England town home to the oldest continuously operating ferry service in the United States.

Glastonbury was initially settled in 1636 and was named after the town of Glastonbury in southwest England’s Somerset County (where the annual Glastonbury Festival is held).

While no such festivals take place in Connecticut’s Glastonbury, the town is popular for its breweries and wineries.

Attractions include Cotton Hollow Preserve and the Minnechaug Golf Course.

Stay at: Hilton Garden Inn Hartford South/Glastonbury

19- Fairfield

Situated along five miles (8 km) of scenic Long Island Sound shoreline, Fairfield in southern Connecticut is home to two university campuses, two public golf courses, five beaches, restaurants and shops.

Fairfield has a population of more than 60,000 residents and is just 57 miles (91 km) from New York City, making it the perfect place to launch day trips to explore the attractions of NYC.

The town of Fairfield’s collection of unique places to explore includes destinations such as the Fairfield Museum & History Center, the CT Audubon Birdcraft Museum and the Fairfield University Art Museum.

Stay at: Sunny & Spacious 2BD 1BA WFH Apt-Huge Yard & Patio

20- Bethel

A colourful downtown district filled with charming shops, restaurants and historic landmarks, Bethel is a quintessential Connecticut town that was the birthplace of entrepreneur and showman Phineas Taylor Barnum.

Bethel was settled in 1855, making it a relatively young town in a state as historic as Connecticut, and is situated just 60 miles (96 km) from New York City.

Bethel’s most popular attractions and cultural institutions include the Putnam Memorial State Park, Circus Moves and the Blue Jay Orchards farmers market. 

Stay at: Tranquil Getaway Cottage in Charming, Bethel CT

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