The 6 Best Places to Live in Connecticut

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Established in 1788, Connecticut is one of the oldest states in the country. You can’t throw a stone without hitting a cute little town that’s packed with history and New England charm. Residents get to experience the beauty of all four seasons—not to mention the plethora of outdoor recreation areas, from ski slopes and foliage-filled trails to flowering meadows and sandy beaches. (And having been born and raised in Connecticut, I can personally say with absolute certainty that it’s a wonderful place to grow up.)

Ready to make the move or just pack your weekender for a few days of suburban splendor? Scroll on for the best spots to live in the Nutmeg State.


1. West Hartford, Ct

Ranked the best place to live in Connecticut three years in a row, West Hartford attracts a diverse group—everyone from young professionals and families to retirees wants to put down roots here. Top-notch schools, kid-friendly happenings like hands-on exhibits at The Children's Museum of Connecticut and steady home values are just some of the selling points. Add to that welcoming residents and spirit of inclusiveness.

Another major drawcard? The well-maintained recreational facilities and leafy neighborhood green spaces. On a nice day, Elizabeth Park is the perfect setting for an afternoon picnic. Be sure to carve out time for a stroll around the West Hartford Reservoir, too. also called out the area’s nightlife. Bars and restaurants line West Hartford Center. Around the corner, Blue Back Square is chock full of shops and eateries.

Places to stay before you make the move:

best places to live in connecticut ridgefield
Doug Kerr/Flickr

2. Ridgefield, Ct

An affluent and adorable town in the foothills of the Berkshire Mountains, Ridgefield's prime perch puts alpine pursuits (think: hiking and biking) at your fingers, err feet. And it’s just an hour from New York City!

Ridgefield has charming colonial architecture and an altogether enchanting vibe. For the 25,000 residents who call this Fairfield County community home, creative attractions such as The Aldrich Contemporary Art Museum, the Prospector Theater and the Ridgefield Playhouse are definitely things to brag about. Locals also tout the excellent schools and a high safety ranking as points of pride.

And while we wouldn’t say it’s inexpensive to buy a pad in Ridgefield, real estate prices remain quite reasonable compared to nearby bank-breakers like Darien and Greenwich.

Places to stay before you make the move:

best places to live in connecticut greenwich
DenisTangneyJr/Getty Images

3. Greenwich, Ct

After a long day making bank, many finance bigwigs retreat to their multi-million-dollar mansions in Greenwich. Just a 60-minute Metro-North train to Grand Central Station, the largest town on Connecticut's Gold Coast comes up big in the desirability department.

Beyond proximity to the Big Apple, highlights include the Bruce Museum and Greenwich Avenue, which boasts a bevy of high-end shops and restaurants. (We highly recommend dining at Mediterraneo). Terrific public schools and private academic institutions like the prestigious Greenwich Academy have a lot to do with the allure, too.

Given all that Greenwich has to offer, the uber-competitive housing market shouldn’t come as much of a surprise. But just to put things in perspective, a single-family home will set you back upwards of $1.43M. Better start saving now...

Places to stay before you make the move:

best places to live in connecticut cheshie
Doug Kerr/Flickr

4. Cheshire, Ct

Nabbing the coveted 28th spot on Money Magazine’s recent list of the top locales to live in America? Cheshire sits halfway between Hartford and New Haven. Though there’s nothing middle-of-the-road about this community of 29,000 residents. The “bedding plant capital of Connecticut” has a sort of pastoral New England appeal. Among its most winsome attributes: horse barns, orchards, gardens and waterfalls in Roaring Brook Park. A manageable cost of living and solid employment opportunities also make Cheshire a practical place to call home.

We dig the small-town charm paired with the fact that it’s close to not one but two major cities. On that note, if you’re craving more urban delights, why not

grab a pie from famed Frank Pepe Pizzeria in New Haven or head to Hartford for live jazz?

Places to stay before you make the move:

best places to live in connecticut simsbury
Andy Leclerc/Getty Images

5. Simsbury, Ct

Another fantastic town in the Hartford area, Simsbury mixes livability, natural beauty and centuries of history. The past is very much alive in this 350-year-old community. To that end, consider checking the Phelps Tavern Museum or the nearby Old New-Gate Prison & Copper Mine.

The Farmington River runs through town. So expect an abundance of activities, from kayaking to fishing. On the outdoor front, you'll also find Talcott Mountain State Park and the trail leading up to the Heublein Tower. Plus, Simsbury has great recreational sports. Kiddos can get involved in town soccer, hockey and lacrosse from an early age.

Hungry? Snag a reservation at Metro Bis, an award-winning restaurant inside the Joseph Ensign House that’s helmed by acclaimed chef Chris Prosperi. Millwrights

and Abigail's Grille are two other standout local favorites.

Places to stay before you make the move:

best places to live in connecticut westport
Michael Levine-Clark/Getty Images

6. Westport, Ct

Poised on the Long Island Sound, the vibrant enclave of Westport will steal your heart with its mix of coastal appeal and cosmopolitan ambiance.

Activities abound. Spend the day frolicking at Compo Beach or Sherwood Island State Park. Play a few rounds of golf. Shop til you drop along Main Street. Dine on the banks of the Saugatuck River. Or catch a show at the Westport Country Playhouse. Planning a summer escape? Levitt Pavilion puts on free concerts during the warmer months.

Residents really love the top-rated schools and contemporary shore homes. (For visitors, that translates to fabulous seaside rentals.) Everyone can agree that the Westport Farmers Market is not to be missed. While you’re there, don’t forget to swing by the Westport Historical Society.

Places to stay before you make the move:

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Freelance PureWow Editor

Lindsay Cohn is a travel writer and serial trip planner who has visited 46 countries across six continents (and counting). When not globetrotting, she’s most likely either doing...