Living in Fairfield, CT: What Makes This Town Great

Fairfield is not a bedroom community with a coffee shop. It is a coastal town of roughly 66,000 people with a real downtown, three train stations, two universities, and five public beaches. I have lived here for most of my life, and this is what I believe makes it one of the best places to live in Connecticut.

A Town, Not a Suburb

Fairfield covers roughly 30 square miles along Long Island Sound, about 50 miles from New York City, and holds more than a dozen distinct neighborhoods. What surprises most people who move here from elsewhere in the county is how much town there is. Well over a hundred places to eat, thirty public tennis courts, a theater that books music year round, and a marina with room for roughly 600 boats all sit inside one town line.

It is also the only town in Fairfield County where you can walk from the beach to town and on to the train in less than 30 minutes. At the same time, its northern end still has two-acre zoning and horse farms. Fairfield delivers something close to city convenience inside a town that still feels like New England.

Five Beaches and a Lake

For most people the beach is a summer idea. In Fairfield it is a daily one. The town maintains five public beaches: Penfield, Jennings, Sasco, Southport, and South Pine Creek. Jennings covers twenty-seven acres with concessions, volleyball, sailboat racks, and the Sand Castle Playground. Penfield adds concessions, a playground, and pavilions that can be rented year round for weddings and events.

Entry to the beaches is free all year. A sticker is required to park in season, and non-residents can buy a daily pass. The town holds its fireworks at Jennings and Penfield in early July, typically on the 3rd rather than the 4th.

Inland, Lake Mohegan sits inside roughly 170 acres of open space around a 17-acre lake, with the only supervised freshwater swimming in town, a sprinkler park, trails, and the Cascades, where the Mill River runs over rock ledges. It is one of the most popular walks in Fairfield, and dogs are welcome.

Three Train Stations and Six Highway Exits

Very few towns on the New Haven Line have three Metro-North stations. Fairfield has Fairfield, Southport, and Fairfield–Black Rock. From Fairfield or Fairfield–Black Rock, Grand Central runs roughly seventy-five to eighty minutes on a peak express, and Stamford is about twenty-five minutes by rail. Fairfield–Black Rock is the one station in town with parking capacity and no permit requirement.

By car, I-95 gives Fairfield six exits, 19 through 24, which is an unusual amount of access for one town. The Merritt Parkway adds Exit 27 at Black Rock Turnpike and Exit 28 at Easton Turnpike. Commuting is not an afterthought here. It is built into the map.

A Real Downtown

Downtown Fairfield is a compact, largely independent district of street-level storefronts around Sherman Green and the train station. The center carries a Walk Score of 84, which Walk Score rates as Very Walkable, and roughly forty of the town’s restaurants are within that walkable core. The Brick Walk anchors it with shops, dining, and apartments above the storefronts, and the Fairfield Theatre Company on Sanford Street runs two venues, StageOne and The Warehouse.

The dining range is wide: Colony Grill and Sally’s Apizza, Bodega Taco Bar, Mecha Noodle Bar, Barcelona Wine Bar, Centro, and Flipside, up to Paci and Artisan at the Delamar in Southport. Beyond the supermarkets there is a genuine specialty layer, including Nordic Fish Market, The Pantry and the Fairfield Cheese Company downtown, Isabelle et Vincent for French baking, Flour Water Salt Bread at the Brick Walk, and the Sunday farmers’ market on Sherman Green from June into October. Elicit Brewing Company on Black Rock Turnpike is the town’s brewery.

Room to Play

Fairfield is built for people who like to be outside. The town maintains thirty outdoor tennis courts across nine sites, an indoor tennis center on Old Dam Road, and thirty-eight pickleball courts with free open play from April through November. There are two municipal golf courses, H. Smith Richardson and the Carl Dickman Par 3, along with three private clubs.

Add thirty-six playing fields, twenty-six playgrounds, a skate park at Jennings Beach, and about 170 acres of parks. In Greenfield Hill, Brett Woods Conservation Area covers roughly 186 acres of woods and trails, and the Connecticut Audubon Society’s Larsen Sanctuary on Burr Street adds another 155.

Schools and Universities

Fairfield Public Schools operates eleven elementary schools, three middle schools, and two high schools, Fairfield Ludlowe and Fairfield Warde, along with an early childhood center. Independent options include Fairfield College Preparatory School, Fairfield Country Day School, Notre Dame Catholic High School, and The Unquowa School. Two universities call the town home: Fairfield University on North Benson Road and Sacred Heart University on Park Avenue. Roughly three dozen licensed childcare and preschool programs operate in town as well.

A Calendar Worth Planning Around

Part of what makes Fairfield feel like home is its traditions. Each spring, the Greenfield Hill Congregational Church hosts the Dogwood Festival, named for the roughly 30,000 dogwoods that bloom across the neighborhood. In the fall, the Greenfield Hill Improvement Society holds its pumpkin festival. Each year, Rooms with a View at the Southport Congregational Church invites designers to build room vignettes, with proceeds going to charity.

Pequot Library in Southport, founded in 1889, runs exhibitions, programs, and a book sale that draws people from well outside Fairfield. In Stratfield, an all-volunteer village association fills Lincoln Park with live music every September. These are not events you drive to. They are part of the neighborhood you live in.

Choosing Where in Fairfield

Fairfield is not one market. It is a dozen small ones, and the difference between them is not a matter of better and worse. It is a matter of fit. A quarter-acre street near the university and a two-acre lot in Greenfield Hill are the same town, the same tax rate, and the same beach stickers, and almost entirely different daily lives. Choosing Fairfield is not the decision. Choosing where in Fairfield is. I have written a guide to the town and to each of the areas I am asked about most:

• The Town of Fairfield: the whole town at a glance, from the trains to the beaches
• The Beach Area: the most walkable market in Fairfield, closest to downtown and the train
• Southport and Sasco: a historic harbor village, its own ZIP code, and two-acre lots on the water
• The University Area: the heart of town, with easy access to downtown, I-95, the train, and the beaches
• Greenfield Hill: two-acre zoning, horse farms, and the dogwoods
• Lake Hills, Lake Mohegan and Fairfield Woods: water, quiet, and more land for the money
• Stratfield: approachable pricing, early-1900s architecture, and Brooklawn

Why Fairfield Is Home

I grew up in Greenfield Hill, moved to the University area in 2013, and moved to Fairfield Beach in 2026. I have spent most of my childhood and all of my adult life here, and there is no other town I would have raised my son in.

Life in Fairfield is about more than beautiful homes. It is about the morning walk on the beach, the train that is closer than you expected, and a downtown you can reach on foot. That is what I am really helping people buy when they choose Fairfield.

Thinking about the move from the city? My relocation guide covers the commute, the tax picture and the timeline, and I compare the county’s best commuter towns.

If you are considering buying or selling in Fairfield County, I am here to help. With more than 15 years of experience and a deep understanding of the local market, I can provide the guidance and strategy you need to make your next move a confident one. Reach out anytime. I would love to connect.

— Shoshana Snyder, Homes by Shoshana