2023 Places to Live in Fairfield Connecticut

Life in Connecticut offers a blend of the active and relaxing, the natural and cultural, the historical and innovative. You will find a mix of city and country living option, access to great health care and excited job opportunities. It's this complementary balance that makes Connecticut such an ideal place to make a great living — while also creating a rewarding life. 

1- Westport

Westport is a trending city for good reason. As a fairly large city, they have a bustling shopping center (you'll have to go off the main drag for the local boutiques), great restaurants that run the gambit from Steakhouses to Japanese, to Vegan based, and homes in various locations, price points and styles- most equipped with plenty of backyard space. Most residents enjoy beach access since there are THREE beaches in Westport- a HUGE perk. There are also yacht clubs, and nearby docking capacity if boating is what you love.

Best of all? It is family friendly and sustainable. There are programs galore for kids and families for both in a studio/classroom or on the water. There are a handful of preserves and hiking trails to explore, and the town was recently awarded the highest marks for sustainability. There are stores that focus on bringing in goods made from recycled goods only, plenty of consignment/second hand stores, and Sustainable Westport which is constantly creating initiatives to make things greener.

2-WESTON

Whether you’re looking for family fun for the weekend or activities to do with your days off, Weston, Connecticut will have something to do. Check out the art scene and restaurants in the community. Nature is the first thing that comes to mind when thinking of this sleepy town with offerings such as the Devils Den preserve that weaves around Saugatuck Reservoir. The community is also packed with Country Cubs and social clubs that bring the community together.

Not big hikers, it is worth checking out the Lactat Town Farm with the family, or just sit and enjoy the quiet beauty of this town. Move here for the nature, but stay for the community.

Sustainability is also a big part of the town culture, with Weston, CT as they recently were named one of Fairfield's most sustainable towns!

3- Greenwich

Greenwich is one of Connecticut's oldest towns, founded in 1640 as a farming community. Today, it's known as one of the Gold Coast's most prestigious suburbs that offers big-city amenities with small town charm. Its location near New York City makes it an ideal commuter town for working professionals who want to be close enough to enjoy all the benefits of living in Greenwich but not so close they feel like they're living in Manhattan.

The largest city in Connecticut’s Gold Coast region, Greenwich features a bustling economy, and is only an hour outside of New York City making it extremely popular among commuters looking for easy access to both areas without sacrificing their quality of life or sense of community (or having to drive through traffic).

This town also offers some of the best restaurants outside of the city with big name chefs opening spots downtown, fresh seafood and mixologists that feel like they were plucked straight from the city.

Greenwich also boasts one of the prettiest beaches in the area, with resident only access in the summer. There is also boat docking and yacht clubs at the ready, and lots of community focused activities throughout the year.

4-Redding

Redding is the town that you didn't know you needed to visit. I always joke that if I ever left Pound Ridge, it would be for Redding. This off the beaten path town produces curvy roads with beautiful vistas, ample hiking, and lakes at every turn. Ample parks produce ample running trails too, with Huntington State Park and Putnam Memorial State Park being some of the most well known. The town also boats  a 40,000 daffodils farm on 70 Cross Hwy.

No matter if your ideal escape is high in the hills or on the lake life, you'll enjoy Redding. There are many local businesses that have families and couples in mind. Redding is close to many surrounding towns, so foodies celebrate! You can still access some of the greatest restaurants in the area! Better yet? The train leaves out of Bethel, CT to the city which is just a few miles away!

5-Stamford

Stamford is the biggest city outside of the city. Samford has a great night life, unique restaurants for a fun eating experience, and is growing. Many professionals who want to move out of the city flock to Stamford. Stamford takes things seriously, from their own micro-breweries to the holiday season, there is never a shortage of things to do and celebrate!

Stamford is the second-largest city in Connecticut with a population of over 130,000 and is the fastest-growing city in the state with a rapidly growing millennial population. Families love it here! It is one of the safest cities in America (FBI ranking), full of parks, community events, and a close proximity to the city (only 50 min on the express)! It also allows for boat docking, plenty of water activities, and year round sports activities. It is also home to Stamford Nature Center which is a family favorite of ours and is worth checking out!

If you want a slower feel, head down to Cove Point Beach (a perk for residents), or Harbor Point for a date night or family day. Stamford is in Fairfield County is on of the best places to live in Connecticut. There is truly something for everyone from spread out larger properties with privacy, to a suburban feel within walking distance to shops and restaurants. 

6- Wilton

Wilton is also home to the only National Historic site in Connecticut, Weir Farm. This modern residential town is rich in New England history. Originally, Wilton began as a farming town, and throughout the decades has transformed into a suburban community.

Wilton was classified as a "dry" town until 1993, when the local ordinance was altered to permit the sale of alcoholic beverages in restaurants. The town was then referred to as "damp."

What really brings people here? Donuts. No seriously... you need to check out Rise Donuts, they have my heart! But, quality of life is the real answer. It offers preserves, hiking, and an incredible sense of peace. Wilton Connecticut is the kind of place where people want to work — because it's the kind of place they love to live. Wilton's quality of life consistently ranks among the top states in the country, thanks to low crime rates, our healthy population and so much more.

LGBTQ+ Rights and public transport

Connecticut is committed to supporting arts and culture through venues, services and programs all over the state. In addition, Connecticut has always been open and welcoming to all communities, including the LGBTQ communities, as we were the 2nd state in the nation to legalize same-sex marriage.

At the hub of the northeast corridor, Connecticut offers a robust network of major highways, commuter rail, Amtrak and Bus Rapid Transit (BRT) routes. And Hartford’s Bradley International Airport is just a flight away from anywhere in the U.S., and Canadian, Caribbean and European destinations.

Check out the best places to see leaves during fall time in Connecticut here.