7 Rank Among Connecticut’s Top 10
It’s back-to-school week here in Fairfield County! Across Lower Fairfield County, backpacks are packed, buses are back on the roads and students are heading into the classroom for the start of the 2026–27 school year.
And if you’re considering a move to Fairfield County, there’s another reason to be talking about schools this week.
U.S. News & World Report just released its 2026–27 Best High Schools rankings, and 7 of Connecticut’s Top 10 public high schools are located right here in Fairfield County.
Greenwich, Weston, Darien, Westport, New Canaan, Wilton and Ridgefield all landed in Connecticut’s Top 10—an incredible concentration of highly ranked public high schools in one county.
For families considering a move to Connecticut, schools are often one of the biggest factors in deciding where to live. But rankings only tell part of the story. Each of these Fairfield County high schools—and the towns surrounding them—offers something different, from standout athletics and theater programs to music, arts, STEM opportunities and strong community involvement.
So, in honor of back-to-school week, let’s take a closer look at 7 of the best high schools in Connecticut and what it’s actually like to live in each of their Fairfield County communities.
#2 Greenwich High School | Greenwich, Connecticut
U.S. News Connecticut Ranking: #2
National Ranking: #194
Greenwich High School is one of the largest public high schools in Connecticut, with approximately 2,500 students. That size comes with an incredible variety of opportunities.
The school offers more than 300 courses, along with extensive extracurricular activities covering academics, service, special interests, the arts and athletics.
Athletics are particularly extensive. Greenwich fields more than 40 varsity teams, with programs that have earned county, state and regional championships. Students can participate in everything from football, soccer and ice hockey to water polo, sailing, rugby, skiing and fencing.
The school also has strong offerings in music, theater, visual arts and other extracurricular programs, giving students opportunities well beyond academics.
What is Greenwich like?
Greenwich is the largest and most diverse—in terms of neighborhoods and housing styles—of the towns on this list. You can find everything from downtown condos to waterfront homes, backcountry estates and neighborhoods that feel surprisingly suburban.
Its proximity to New York City is a major attraction for commuters. Greenwich also offers multiple Metro-North stations, beaches, parks, shopping and dining along Greenwich Avenue, and distinct communities including Old Greenwich, Riverside, Cos Cob and central Greenwich.
For buyers relocating from New York, Greenwich is often one of the first Connecticut towns they consider because of its location, amenities and breadth of housing options.
#3 Weston High School | Weston, Connecticut
U.S. News Connecticut Ranking: #3
National Ranking: #235
Weston High School is considerably smaller than Greenwich High School, with approximately 700 students, making it an interesting choice for families looking for a smaller school environment while still having access to excellent academics and extracurricular activities.
Weston's athletic program offers numerous teams throughout the fall, winter and spring seasons, and the school notes particularly high student participation.
The arts are another standout. Students have opportunities in theater, visual arts, orchestra, chorus, band and jazz. Weston Public Schools has also repeatedly received the Best Communities for Music Education designation from the NAMM Foundation.
Weston High School's Theater Company produces plays and musicals, while the visual arts curriculum includes drawing, painting, photography, graphic design, video production and ceramics.
What is Weston like?
Weston feels very different from the coastal towns of lower Fairfield County. It is wooded, private and residential, with larger properties and a distinctly New England feel.
There is no Metro-North station in town and very little commercial development, which is exactly what many Weston residents love about it. Buyers often choose Weston because they want land, privacy and a quieter lifestyle while remaining within reach of Westport, Wilton and the rest of Fairfield County.
For someone who wants a strong school system paired with a peaceful, more rural setting, Weston is definitely worth exploring.
#4 Darien High School | Darien, Connecticut
U.S. News Connecticut Ranking: #4
National Ranking: #246
Darien High School serves approximately 1,400 students and combines strong academics with a particularly active school community.
One of DHS's most recognizable strengths is athletics. For the 2025–26 school year, Darien reported 69 athletic teams across 36 sports, including 38 varsity teams.
The Blue Wave competes in everything from football, field hockey and lacrosse to swimming, ice hockey, squash, sailing, rugby and volleyball. Athletics are a significant part of the school culture, but they aren't the only opportunity for students.
Darien also offers music and theater beginning at the freshman level, including concert band, choir, orchestra, percussion, guitar, music theory, music technology, drama and theatrical design.
What is Darien like?
Darien combines the feeling of a smaller coastal New England town with incredible convenience to New York City.
Two Metro-North stations, beaches on Long Island Sound, parks, sports programs and a strong community atmosphere make it particularly popular with families moving from New York City and Westchester.
Downtown Darien has also evolved considerably in recent years with the addition of Darien Commons and The Corbin District, bringing more restaurants, shopping and gathering spaces into town.
Housing ranges from charming older homes close to town and the train to larger properties, newer construction and waterfront homes.
Darien is a town where school, sports and community activities tend to overlap—which can make it surprisingly easy for new families to become part of the community.
#5 Staples High School | Westport, Connecticut
U.S. News Connecticut Ranking: #5
National Ranking: #270
Staples High School serves approximately 1,600 students and is known for combining strong academics with exceptional opportunities in the arts, athletics and extracurricular activities.
One program that really stands out is Staples Players, the school's theater organization. Staples describes it as producing some of the country's best student theater, with students able to participate as performers, musicians and technicians.
Music is another important part of the Staples experience, with opportunities including orchestra, jazz and choral programs.
And, of course, Staples has a robust athletic program competing in the FCIAC.
What is Westport like?
Westport tends to appeal to buyers who want excellent schools but also place a high value on culture, restaurants, recreation and access to the water.
Compo Beach is one of Fairfield County's most recognizable town beaches, and residents also have access to Longshore Club Park with golf, tennis, pools, sailing and other recreational opportunities.
Downtown Westport offers shopping and dining along the Saugatuck River, while the town's arts scene includes the Westport Country Playhouse and a long history of attracting artists, writers and creatives.
Westport also has Metro-North service from the Westport and Greens Farms stations.
For many relocating buyers, Westport offers an appealing combination: schools + beach + culture + community + NYC access.
#6 New Canaan High School | New Canaan, Connecticut
U.S. News Connecticut Ranking: #6
National Ranking: #297
New Canaan High School serves approximately 1,200 students and has strong programs in academics, athletics and the arts.
Athletics play a large role in the high school experience, with teams across football, lacrosse, ice hockey, swimming, soccer, track, tennis, volleyball and numerous other sports.
But New Canaan's theater program deserves particular attention.
New Canaan High School Theatre is an award-winning program that typically produces five productions, including musicals, a play and a student-produced drama festival. Students can become involved in acting, singing and dancing as well as directing, choreography, stage management, lighting, sound, costumes, makeup and set construction.
The program has earned numerous Halo Awards in recent years for productions, performances, costumes and other areas of theater.
What is New Canaan like?
New Canaan offers something many Fairfield County buyers love: a very defined and walkable downtown surrounded by beautiful residential neighborhoods.
Elm Street and the surrounding village have restaurants, boutiques, coffee shops and community events, and the Metro-North station sits right in the center of town.
The town is also known for its architecture, including an impressive collection of mid-century modern homes, alongside Colonials, newer construction and larger estates.
New Canaan doesn't have the coastal setting of Darien, Greenwich or Westport, but buyers are often drawn to its village atmosphere, larger properties, community involvement and strong school and sports culture.
#7 Wilton High School | Wilton, Connecticut
U.S. News Connecticut Ranking: #7
National Ranking: #300
Wilton High School serves just over 1,000 students and offers strong academics alongside athletics and a particularly active performing arts community.
Wilton athletics emphasizes competition, leadership, sportsmanship and character, with programs spanning the traditional fall, winter and spring sports.
Theater is another standout.
Wilton High School Theatre offers multiple opportunities throughout the year, including its student-driven Little Theatre Company and a large spring musical involving actors, singers, dancers, musicians and technical crews. The program received 18 nominations and three awards at the 2026 Halo Awards.
What is Wilton like?
Wilton offers a more relaxed and spacious feel than many of the towns closer to the coast.
Homes often sit on larger lots, and the town has extensive wooded areas, trails and open space. Wilton also has its own Metro-North station, although commuting times are generally longer than from towns closer to the New Haven Line.
Wilton Center provides restaurants, shops and community amenities without feeling overly commercial.
Buyers who like the schools and lifestyle of lower Fairfield County but want more property and a quieter setting often put Wilton high on their list.
#9 Ridgefield High School | Ridgefield, Connecticut
U.S. News Connecticut Ranking: #9
National Ranking: #439
Ridgefield High School rounds out Fairfield County's representation within Connecticut's Top 10.
RHS offers a rigorous academic curriculum along with a wide range of extracurricular opportunities.
Athletics are an important part of school life, with Ridgefield competing in the FCIAC and fielding teams across numerous boys' and girls' sports.
Students also have access to electives and programs in art, theater, music, business and technology, giving students opportunities to pursue interests outside traditional academics.
What is Ridgefield like?
Ridgefield is the northernmost town on this list and feels more like a classic New England country town.
Its beautiful Main Street, historic architecture, restaurants, shops and strong arts community give Ridgefield a very distinct personality.
Homes often offer more land and square footage for the price compared with towns closer to New York City and the coastline. The tradeoff is the commute: Ridgefield does not have its own Metro-North station, so commuters typically drive to nearby stations.
For buyers who don't need to commute into Manhattan every day, Ridgefield can offer an appealing combination of highly ranked schools, a vibrant town center, larger properties and a strong sense of community.
Why Are So Many of Connecticut's Top Schools in Fairfield County?
There isn't one single reason.
Fairfield County communities tend to place a significant emphasis on education, but the appeal goes beyond what happens inside the classroom.
In many of these towns, schools become a major part of community life. Friday night football games, theater productions, concerts, youth sports, school fundraisers and community events bring families together long before—and long after—their children reach high school.
Strong schools and strong communities often go hand in hand.
And from a real estate perspective, highly regarded school systems can be an important contributor to sustained housing demand.
Families moving into Fairfield County aren't simply buying a house. They're often choosing a town based on an entire lifestyle: schools, commute, beaches, recreation, sports, arts, downtowns, property size and community.
That continuing demand—combined with limited housing inventory in many Fairfield County towns—is one of the factors that can help support home values over the long term.
Which Fairfield County Town Is Right for You?
The interesting thing about Fairfield County is that these seven towns are relatively close geographically, yet the experience of living in each can be completely different.
Want coastal living and an easier Manhattan commute? Explore Greenwich, Darien and Westport.
Want a walkable New England village? Take a look at New Canaan.
Want more land and a quieter residential setting? Weston and Wilton may be a better fit.
Want a quintessential New England town with more space and don't need to commute to NYC every day? Ridgefield deserves a look.
School rankings are useful, but I always encourage buyers to look beyond a number. Consider the programs that matter to your children, visit the towns, explore the neighborhoods and understand what everyday life will look like.
Because ultimately, you're not just choosing a school.
You're choosing a community.
If you're considering a move to Darien, Greenwich, New Canaan, Westport, Wilton, Weston, Ridgefield or anywhere in Lower Fairfield County, I'd be happy to help you compare the towns, neighborhoods, commute and housing options and determine which community best fits what you're looking for.
School rankings referenced are from the U.S. News & World Report 2026–27 Best High Schools rankings. Rankings and school programs can change from year to year. Buyers should independently verify current school assignments, enrollment information and educational programs directly with the applicable school district.