Welcome to Fairfield & Southport
Fairfield is the commuting middle ground, convenient in every direction. With three Metro-North stations, Fairfield, Fairfield Metro and Southport, New York commuters have options, and from I-95 or the Merritt Parkway you have easy access to the city or New Haven. It is also a university town, home to Fairfield University and Sacred Heart University, and a quintessential beach community, with five public town beaches along Long Island Sound. After more than 20 years of living in Fairfield, these are the places we love most.
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Fairfield, CT Schools & Public Education Guide
Fairfield Public Schools serves the town with 18 schools: 11 elementary schools, three middle schools and two high schools, Fairfield Ludlowe and Fairfield Warde, along with an early childhood learning center and an alternative high school. Students can also apply to regional magnet programs, including the Regional Center for the Arts in Trumbull, the Center for Global Studies in Norwalk and the Aquaculture School in Bridgeport.
Our must-tour private school is The Unquowa School, PreK through 8th grade and founded in 1917. My daughter was blessed to go there from pre-K through 8th grade, and there is no place like Unquowa. Its child-centered approach meets each student where they are and prepares them for lifelong success, from Early Childhood through Lower School and Upper School.
Other private schools of note include Fairfield Country Day School, an all-boys day school for kindergarten through 9th grade founded in 1936; The Southport School, formerly Eagle Hill Southport, for students in kindergarten through 8th grade with language-based learning differences; and Notre Dame Catholic High School, a coed Catholic high school for grades 9 through 12.
Fairfield is a true university town. Fairfield University and Sacred Heart University bring lectures, performances, athletics and campus energy to the community.
School assignments and programs may change. Buyers should confirm directly with the district.
Fairfield & Southport Local Amenities & Lifestyle Highlights
Arts & Culture
In Southport, the Pequot Library, a Romanesque Revival landmark that opened in 1894, is a cultural treasure. Its special collections include a 1632 Shakespeare folio and Audubon's The Birds of America, with a new print turned each month. It hosts a Meet the Author series and lectures, and its summer book sale, often called the largest in Connecticut, draws thousands every year.
The Connecticut Audubon Society's Birdcraft Museum and Sanctuary, founded in 1914 by Mabel Osgood Wright, is one of the oldest songbird sanctuaries in the country. Audubon offers classes on local wildlife and guided nature walks for all ages.
The Fairfield Museum and History Center brings the town's storied past to life with rotating exhibits, artifacts and community events.
The Fairfield Theatre Company, a nonprofit center for arts and culture in the heart of downtown, brings together musicians, actors, artists, writers and fans with the belief that live entertainment keeps a community vibrant. It hosts shows across four spaces: the intimate 225-seat StageOne, The Warehouse with room for 640, The Lot for outdoor shows and The Gallery, run by Art/Place Gallery. Its stages have hosted Jason Mraz, Little Feat, Buddy Guy, Keb' Mo', Hot Tuna and 10,000 Maniacs, plus early shows by The Lumineers, Trombone Shorty, Goose and The Revivalists before they hit it big. Check the calendar for upcoming shows. It is also a killer place for corporate events.
Downtown's old movie theater on the Post Road, opened in 1920 and dark for nearly a decade, was revived by Sacred Heart University and reopened in 2021 as the Sacred Heart University Community Theatre, with films, concerts and talks. The Fairfield Public Library rounds out the calendar with author talks, workshops and programs for all ages.
For gardens, in our opinion the best nursery in town is Oliver Nurseries. Ganim's Garden Center and Outdoor Design & Living are also local favorites, and there is always Home Depot.
Outdoors & Coastal Recreation
Fairfield is a quintessential beach community, with five public town beaches: Jennings, Penfield, South Pine Creek, Sasco and Southport. Our personal favorite is Sasco. It is the local spot: not crowded, quiet and the perfect place to enjoy a good book and a sunset.
As a Fairfield resident, you can reserve a beach bonfire for an evening gathering, with a permit, from May through September. Town beaches are open until 11 p.m. in season. Every Fourth of July, the town's fireworks light up the sky over Jennings and Penfield beaches.
One of my favorite memories from when my daughter was little was the annual Unquowa field trip to tag horseshoe crabs at the beach with Project Limulus, Sacred Heart University's long-running research program.
Country Clubs, Yachting & Golfing
Clubs: The Patterson Club, first organized in 1929 by the General Electric Company, sits on 163 bucolic acres in Greenfield Hill. It offers an expansive clubhouse, an 18-hole Robert Trent Jones Sr. golf course, seven tennis courts and four pickleball courts, five paddle courts around a paddle hut with a stone fireplace, and a full aquatics area with heated pools and outdoor dining. The Country Club of Fairfield, opened in 1914, sits beside Long Island Sound with a Seth Raynor course. The Fairfield Beach Club, on Fairfield Beach Road between Jennings and Penfield, offers private beachfront, a pool, tennis and paddle tennis, dining and youth sailing.
Boating: On historic Southport Harbor, the Pequot Yacht Club, founded in 1920, is as distinguished as you'd expect, with a clubhouse, moorings, a fuel dock and a Junior Sailing program. The town runs South Benson Marina, with room for more than 600 boats and two launch ramps, and the historic Ye Yacht Yard on Southport Harbor, with small-boat slips, moorings and kayak racks. Slips are for Fairfield residents, and waitlists run from a couple of years for small boats to more than a decade for large ones, so get on the list early.
Golf: The town's H. Smith Richardson Golf Course is a local favorite, and the course still hosts a tournament named after my childhood dog, an English Setter. The Higgins Cup honors Higgins, who was famous for walking the greens with my dad and chasing away the Canada geese. The nine-hole Carl Dickman Par-3 Golf Course at South Pine Creek is perfect for a quick round, and Fairchild Wheeler Golf Course, owned by the City of Bridgeport, sits within Fairfield's borders. The Patterson Club and the Country Club of Fairfield round out private golf.
Parks, Lakes & Preserves
Lake Mohegan is a freshwater oasis with wooded hiking trails and summer swimming, perfect for a dog walk or an afternoon outing. Henry Rowland Park, known to locals as "The Sand Castle," is a playground built around a giant castle. Just over the line in Bridgeport, the Adventure Park at the Discovery Museum offers aerial trails and zip lines, and the Sportsplex at Fairfield covers indoor sports from ice skating to rock climbing.
One of our favorite lake neighborhoods in Fairfield County surrounds Samp Mortar Lake, a reservoir created by a 1901 dam on the Mill River. The neighborhood's LakeHills Association offers swim lessons, a swim team and lifeguarded swimming for members. Next door, the town's 7.3-acre Samp Mortar Open Space has steep, rocky trails past glacial boulders and a 30-foot cliff to Samp Mortar Rock, where Native Americans ground corn in a round hollow in the stone, and a red loop leads to a promontory overlooking the lake.
For horseback riding, Salko Farm & Stables is the local spot, right here in Fairfield. Just over the line in Westport, the Fairfield County Hunt Club, organized in 1923, hosts annual events including its June Horse Show, which marked its 100th anniversary in 2024, and summer polo, and it has a new tennis building.
The Fairfield & Southport Lifestyle
Food & Restaurants
The best new sushi is Hotaru in Southport, an intimate 30-seat omakase spot with great service, unique options and great value for a special night out.
One of our favorite spots for a special night out is Esh, a contemporary take on the cooking of the Middle East and Mediterranean, from Israel and Lebanon to Turkey, Greece and Morocco. Expect vibrant flavors and aromatic spices, reimagined with a modern twist.
For wine and tapas, Barcelona Wine Bar is a summer go-to for its outdoor patio, with an incredible wine list and cocktails. Share small plates and favorites like paella and the parrillada mixed grill, which also makes an excellent takeout order to feed a group.
Mecha Noodle Bar on the Post Road is a local favorite and hot spot for all ages. From authentic pho to ramen, hot oil dumplings and bubble tea, nothing beats a steaming bowl of noodles.
Super Duper Weenie on Black Rock Turnpike is a Fairfield institution. Gary Zemola makes his own dogs and casings to his exact specifications, plus relish and toppings in house, and the restaurant has drawn national attention from PBS, Food Network, Late Night with David Letterman, Roadfood and Diners, Drive-Ins and Dives. From a New England to a Chicago with house-made hot relish: one of each, please, and a large fry made on the spot.
Also on Black Rock Turnpike, Layla's Falafel has served family recipes for 20 years. The garlic sauce is heaven, and it will keep the vampires at bay for at least two days. The Arabic chicken shawarma wrap is a thing of beauty; my daughter could eat a whole one by herself at four years old. The grape leaves are the best I've ever had.
Bagels on the weekend from Bagel King are as close to New York bagels as you get in Connecticut. The house-made cream cheese can be taken to go, and the flagels are flat, chewy and worth the carbs.
Isabelle et Vincent is a Parisian patisserie known for its bread, made from a starter that came directly from France with the original owners. The beignets are a thing of beauty, and no holiday gathering is complete without a big box of colorful macarons.
The downtown sandwich spot is Firehouse Deli on Reef Road, serving Fairfield since 1969, with a salad bar and sandwiches that have been voted among the best in Fairfield County.
For a quick weeknight dinner at home, Centro Ristorante & Bar on the Post Road offers the Best Deal in Town: your choice of homemade pasta and house-made sauce to cook at home, with a Caesar salad, brick-oven Italian bread and marinated olives, sized for two or four.
There's a reason Connecticut is the pizza state: it's the best in the country. New England pizza legends Frank Pepe's and Sally's Apizza both have Fairfield locations, but the local favorite is NautiDolphin, steps from the Fairfield train station. My daughter's favorite weekend activity was dinner at the beach with friends and a NautiDolphin pizza.
And then there's Colony Grill, the kids' favorite spot. Born as a Stamford tavern in 1935 and grown by Connecticut locals who grew up together, it serves one thing and does it perfectly: the thin-crust bar pie topped with its famous hot oil.
For commuters, the best coffee on the run is Wake Cup Coffee, right at the Fairfield Metro station.
Nightlife
Elicit Brewing Co. on Black Rock Turnpike combines a brewery, beer hall, speakeasy, biergarten and restaurant under one roof, with craft beer, cocktails, food, live music and late nights on the weekend.
A hidden gem downtown, J.B. Percival Co. is an intimate speakeasy-style lounge tucked on Donnelly Walk off Unquowa Road, with crafted cocktails, small-batch spirits and light bites. It is perfect for a drink before a show, with trivia on Wednesdays and live music on Thursdays.
Still there after all these years, The Seagrape on Reef Road is the beach-area watering hole that has carried its name since the 1980s, with live music, open mic nights, pool, darts and its famous tots.
Just over the line in Bridgeport's Black Rock neighborhood, Park City Music Hall on Fairfield Avenue is a social club for live music, art, dancing, food and drinks, with a nonprofit arm that brings music education to Bridgeport.
For big-name concerts, the Hartford HealthCare Amphitheater is minutes away on the Bridgeport waterfront, a 5,700-plus-seat boutique venue on Long Island Sound. Its stage has hosted The Beach Boys, Willie Nelson's Outlaw Music Festival, The Doobie Brothers, Steve Miller Band, Melissa Etheridge, Darius Rucker, Tedeschi Trucks Band and Jerry Seinfeld, and Matchbox Twenty with David Gray is already on the calendar for July 2027.
Groceries
Trader Joe's is on Black Rock Turnpike, and Whole Foods is on Grasmere Avenue.
Shopping
For books, the Fairfield University Bookstore on the Post Road downtown is a community favorite for browsing and gifts.
The best local wine shop in town is Harry's Wine & Liquor on the Post Road, Fairfield's original corner liquor store since 1941 and now in its third generation. The staff is stellar and knowledgeable, the selection of rare whiskeys and bourbons is unmatched, and Harry's gives back every year. Each October, its Operation Hope Rules fundraiser supports Operation Hope with whiskey raffles, auctions and rare bottle releases.
Downtown, the Post Road is lined with local shops and boutiques, from Jane + Mercer, Ciao Bella, Apricot Lane and Lolli Sutton to Bluepoint Home, Henry C. Reid Jewelers and Marathon Sports, with more gems around the corner on Reef Road and Unquowa Road. Southport Village is known for antiques and specialty finds. The RH Outlet, which opened in 2024 in the former Bob's Store space at the Fairfield Shopping Center on the Post Road, offers discounted luxury furniture, lighting, textiles and decor, including clearance, returns and overstock, often at deep markdowns. Inventory changes often, so it pays to stop in regularly.
The best local home goods shop is The Beehive on the Post Road downtown, with curated gifts, home accessories and furnishings, plus interior design services.
Big-time CT love lives at The Two Oh Three, named for the 203 and Fairfield's own lifestyle brand, started in 2014 by siblings Tory and Roscoe Brown in their parents' basement. Its Fairfield shop carries apparel, hats, drinkware, home goods and gifts that celebrate the state's coastal charm.
Annual Events
The Memorial Day Parade brings out the whole town to honor those who died in service to our country. It steps off at 10 a.m. at the Post Road and South Pine Creek Road, heads east to the library, then follows Old Post Road past Flint's Corner and the Town Green, with floats, local bands, veterans groups like American Legion Post 143, and school teams and athletes marching. Neighbors set out chairs, blankets and flags along the route in advance, and the day often includes a Sea Ceremony at South Benson Marina.
Every Halloween, Fairfield's famous MOMbies dress as zombies and perform their show-stopping Thriller dance through the neighborhood, raising money for metastatic breast cancer research. Their performances have gone viral far beyond Connecticut, and they are a great example of how close-knit the community is, especially in the beach area.
Halloween also means the annual Rocky Horror Picture Show screening from Fairfield Center Stage, complete with a live cast, audience participation, props and costumes for everyone.
Every June, runners line up at Jennings Beach for the Fairfield Road Races, a weekend of races that includes a half marathon, a 5K, a beer mile and a kids' fun run.
COMMUTE TIME TO NYC
Fairfield is about 50 miles from New York City, roughly an hour and a half by car. Metro-North serves three stations, Fairfield, Fairfield Metro and Southport, with trains to Grand Central in about an hour and a half, and I-95 and the Merritt Parkway put New York and New Haven within easy reach.
