Welcome to Westport
Westport, CT offers a blend of coastal beauty and vibrant community life, beckoning all who seek its unique lifestyle. The town's schools, impressive coastline, and architecturally captivating neighborhoods serve as initial draws. That said, it's the enduring sense of genuine community warmth and togetherness that keeps people rooted in Westport.
I'm Carrie Klein Perkins of Spaces Real Estate and the author of this community guide. Westport, Connecticut, has been my workplace for more than 35 years. I'm a second-generation real estate professional who started answering the phones in my mother's real estate office at age 12. At 16, before college, I landed my first Main Street job at Banana Republic, back when Jeeps hung from the ceiling, safari wear filled the racks, and Paul Newman and Robert Redford would occasionally pop in together. A lot has grown up and changed since then. What hasn't: the views of Long Island Sound and the Saugatuck River, a storybook downtown in every season, and a food scene that ranks among the best in the state, with something for everyone. I know Westport's neighborhoods, beaches and back roads the way only decades here can teach you, and I bring that local knowledge to every home I help buy or sell. I'm also here to help with everything after the move, from where to find the right preschool, salon or home goods to trusted service providers for every kind of home maintenance. We are your go-to resource for life.
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EDUCATION
Westport Public Schools serves the town with five elementary schools (Coleytown, Greens Farms, Kings Highway, Long Lots and Saugatuck), two middle schools (Bedford and Coleytown) and Staples High School. A new Long Lots Elementary is under construction on Hyde Lane, a 128,000-square-foot replacement expected to open in 2027.
Staples is known for its arts, and Staples Players is the headliner. The program began in 1959 when student Christopher Lloyd urged a teacher to put on a show. Alumni include Justin Paul, co-writer of Dear Evan Hansen and La La Land; Liz Hannah, screenwriter of The Post; Alisan Porter, winner of The Voice; and Britt Baron of GLOW.
Private schools of note include Greens Farms Academy, a PreK–12 school on a former Vanderbilt estate overlooking Long Island Sound, and Pierrepont School, an independent K–12 school founded in 2002. Next door in Fairfield, The Unquowa School, founded in 1917, serves grades K–8 and is open to students from all towns.
For preschool, Landmark Preschool, now part of the Ridgefield Academy community, has taught young children for 40 years and has a campus in Westport, with low student-teacher ratios. The Earthplace Preschool has taught on the grounds of Earthplace's 62-acre nature sanctuary, the largest open space in Westport, since 1967 and is NAEYC accredited. Nearby, the Montessori schools are also well liked: The Montessori School in Wilton, which continues through grade eight, and Great Beginnings Montessori on Beach Road in Fairfield, for ages 22 months to 12 years. Farther afield, Fraser Woods Montessori School in Newtown, for ages 15 months to 14 years, is very well respected and draws students from all over.
For music, Suzuki Music Schools, a nonprofit community music school on Post Road East, starts the youngest musicians with early childhood music classes from birth to age 3, then offers instrumental lessons, ensembles, an honors program and summer camps, with adults welcome too.
School assignments and programs may change. Buyers should confirm directly with the district.
AMENITIES
Arts & Culture
The Westport Library is the town's intellectual and creative hub. Its two-year transformation reopened the building in 2019 on the Saugatuck River beside Jesup Green, with a makerspace, a grand forum for talks and performances, and Verso Studios, a professional recording studio whose label released the first vinyl album recorded, produced and released by a public library. It also hosts incredible speakers: 2026 brought NBC's Craig Melvin, journalist Jelani Cobb and Wyclef Jean headlining VersoFest, plus the annual Westport Prize for Literature. Its signature gala, BOOKED for the evening, marked its 27th year in October 2026 with Debbie Allen in conversation with Shonda Rhimes. Past honorees include Sarah Jessica Parker, Billie Jean King, Laura Linney, Martin Scorsese and Tom Brokaw.
The Westport Country Playhouse has been a landmark since 1931, when Lawrence Langner and Armina Marshall Langner turned an 1835 tannery into a theater. Once a Broadway tryout house, it was renovated in 2005 under artistic director Joanne Woodward and is now a nonprofit growing into a year-round performing arts center and a community hub for theater, art, ideas and fellowship. Under artistic director Mark Shanahan, the 2026/2027 season brings Ken Ludwig's Pride and Prejudice, Part 2: Napoleon at Pemberley, A Sherlock Carol, Murder For Two and The Legend of Georgia McBride, plus concerts like Christine Ebersole's Home for the Holidays. The Pancake Club, which drew Marsha Mason, James Naughton and Tony winner Judith Ivey to a Script in Hand reading in January 2026, returns as a full production in spring 2027. See what's on and get tickets. Make it dinner and a show for a New York night out without the train ride.
Longtime Westport residents Joanne Woodward and Paul Newman were the Playhouse's cultural and financial saviors. Woodward became artistic director in 2000 and launched the campaign to transform it from a struggling summer-stock theater into a year-round regional institution. Newman starred in the 2002 revival of Our Town, which sold out and moved to Broadway. Star friends including Carole King, Robin Williams, Robert Redford and Harry Connick Jr. headlined benefit galas toward a $30.6 million campaign goal, and after an 18-month renovation, the Playhouse reopened in 2005 for its 75th anniversary season.
The Levitt Pavilion for the Performing Arts is an open-air stage on the Saugatuck River with more than 50 nights of free entertainment each summer, from jazz to rock to world music, plus ticketed headliners that help fund it. The 2026 season brought Bonnie Raitt and The Revivalists; watch the Levitt's site for the 2027 lineup. Bring a blanket and claim your spot on the lawn.
MoCA CT, formerly MoCA Westport, presents contemporary art from its Newtown Turnpike campus, with rotating exhibitions, artist talks and programs for all ages.
Blau House & Gardens is a 1962 mid-century modern home designed by Broadway set designer Ralph Alswang, surrounded by gardens Barry Blau shaped over roughly 50 years. Newly listed on the Connecticut State Register of Historic Places, it is open for tours and programs by appointment.
Community Recreation
Longshore is a gem in town: an 18-hole municipal golf course right on Long Island Sound, with tennis, a public pool, the Inn at Longshore and the Longshore Sailing School, open to the public with lessons and sailboat, kayak and paddleboard rentals. In winter, it converts into an outdoor skating rink. A town master plan for the 168-acre park is underway.
The Westport Weston Family YMCA, which celebrated its centennial in 2023, is based at its expanded Bedford Family Center on the wooded Mahackeno campus off Wilton Road. I took ballet at the Westport Y myself. Summer camps include the beloved Camp Mahackeno, Camp Mini Mack and a counselor-in-training program, with after-school care and vacation day camps the rest of the year. Kids' lessons run from swim and gymnastics to dance and basketball, and the Water Rat Swim Team competes year round. Adult classes cover group fitness, personal training, masters swimming, water polo, ballroom dance, a triathlon club and a TrackMan golf simulator.
Fitness & Wellness
TAP, founded by chiropractor and strength and conditioning specialist Dr. EJ Zebro, is about longevity, quality of life and structural integrity, blending preventative care, recovery, hands-on therapy and rehab with customized training. Its small group classes are the best secret in town. Personally, it is the best investment you can make in your health and well-being.
The best way to start or end your day for restoration and self-care is SWTHZ, with private suites for infrared sauna and cold plunge. Cold plunges are having a major moment, and for good reason. If you don't have one at home, Kiin Sauna, a Westport-based traveling wellness experience, brings a wood-burning sauna and cold plunge to you and hosts events around town.
Newly opened on Post Road West, Indigo Wellness Group brings integrative care under one roof: acupuncture and Chinese medicine, functional medicine, nutrition, massage, lymphatic drainage, pelvic floor therapy and more. Founded in 2015 by Dr. Sarah Swanberg, the practice has a team of licensed specialists across its Westport and Stamford locations.
Rowing is for all ages at Saugatuck Rowing Club, one of the few clubs in the county. Juniors start at 11, adults row into their 70s, and alumni include Olympians Cameron and Tyler Winklevoss and Staples graduate Oliver Bub. Seeing the boats go past along Riverside Avenue is a thing of beauty.
Farms, Markets & Gardens
Wakeman Town Farm is a working farm and education center with workshops, cooking classes and youth programs. It co-leads Westport's Pollinator Pathway, a network of pesticide-free yards and public spaces planted with natives.
The Westport Farmers' Market, now in its 20th season, is the best farm market around: local farms and community every Thursday at 50 Imperial Avenue, moving indoors to Gilbertie's for the winter. Through its Staples High School Culinary Program, advanced culinary students cook with market produce for the Gillespie Center community kitchen.
Gilbertie's Herb & Garden, celebrating 100 years, is the best place in town for garden seedlings, with more herbs than anywhere else. In our opinion, it is the place for summer tomato seedlings, with so many to choose from.
We never miss the Aspetuck Land Trust Native Plant Sale each spring at the Haskins Preserve. Every native you plant supports the land trust's Green Corridor, turning private yards into stepping stones for wildlife. See the Green Corridor story map and what homeowners can do to support biodiversity.
Home Resources
Our recommended builder is Redcoat Homes. Christopher Montanaro works alongside his mother, esteemed architect Judith Larson, and the team is known for transforming the village area of Westport, where you can walk to Main Street. See one of their homes in Cottages & Gardens.
Notable architects in town include Cole Harris Associates, recognized by AIA Connecticut for sustainable design; Cardello Architects, led by Robert Cardello and a Moffly A-List winner for modern architecture; and Vita Design Group, Lucien Vita's firm, known for modern design with New England character.
For bespoke kitchen and bath design, Karen Berkemeyer Home is our local resource. For over 30 years, Karen and her team have taken projects from concept to installation, and the Post Road West showroom offers custom cabinetry, tile, stone, countertops, plumbing and fixtures under one roof.
Hard to find anymore: where to get your vacuum repaired. Stanton Miles has served Westport since 1953, repairing every make and model and selling SEBO, Miele and more. We suggest buying from them directly; the warranty and service can't be beat.
OUTDOORS
Westport's town beaches are Compo, Burying Hill and Old Mill. Residents park with a seasonal beach emblem, and Old Mill is for residents only. Our picks are Compo and Burying Hill, a hidden gem.
Compo Beach is the town's summer living room: 29 acres of sand on Long Island Sound at the mouth of the Saugatuck River, with sand volleyball, the Ned Dimes Marina next door and a playground rebuilt by community volunteers in 2025. It also hosts the best fireworks anywhere. The Westport PAL Independence Day fireworks have lit up Compo for more than 60 years, with longtime sponsors Melissa and Doug Bernstein of Melissa & Doug. Tickets sell out, and the beach starts filling up at sunrise.
The Saugatuck River is made for kayaking and paddleboarding, winding past the town center out to the Sound.
Boating is a way of life here. The town runs two marinas, the Ned Dimes Marina at Compo Beach and the E.R. Strait Marina at Longshore, with launch ramps at Compo, Longshore and Sherwood Mill Pond Preserve. In-water slips are for Westport residents, and demand is real: the waitlist runs from about a year for a rowboat to nine years or more for a boat over 22 feet, so get on the list early.
Winslow Park, in the heart of town, is a favorite for dogs and their people, with trails, picnic space and wide, shaded open fields.
Runners line up every spring for the Minute Man Race at Compo Beach, a 10K and 5K run/walk with kids' fun runs. Hosted by the Women's League of Westport to fund local nonprofits, it runs for the 48th time in April 2027.
For cycling, Bike Westport suggests a roughly 13-mile village loop, flat coastal roads around Compo and quiet neighborhood back roads, plus walks along the Library Riverwalk. Westport is also part of the Western New England Greenway, a signed route along Newtown Turnpike and Broad Street that links to the East Coast Greenway and runs north toward Montreal.
LIFESTYLE
Salons
At Salon Dada, Benjamin is a true artist; the wait for an appointment runs months in advance, and it is well worth it. At Bird, Suzanne Baumann is, in our opinion, the best colorist in town.
Food & Restaurants
The new hot spot is Delamar Westport, a boutique inn that opened in 2025 with a lobby and three suites designed by local favorite Christian Siriano. Its restaurant, Dandelion, brings Mediterranean sunshine to the Post Road.
OKO on Wilton Road is the best omakase experience around. Chef Brian Lewis is a James Beard Best Chef: Northeast semifinalist and nominee whose OKO Rye earned MICHELIN Guide recognition in 2021. He is also behind The Cottage, where it is a different experience every time, with off-the-charts ingredients from trusted regional farmers and purveyors and menus that evolve weekly with the season's bounty. Lewis is a proud board member of Experience Camps, a national, no-cost program for grieving children who have experienced the death of a parent, sibling or primary caregiver.
For Italian, Casa Me in Sconset Square serves house-made pastas, pinsa and Negronis on its seasonal terrazza. Downtown off Main, Felice is the perfect spot for lunch with friends. Newly opened Massi Co. on Post Road East is Neapolitan pizza from Massimo Tullio, the restaurateur behind several destination restaurants in town, including The Whelk.
The Whelk has served sustainable seafood and coastal cooking on the Saugatuck River since 2012. Pull up to the raw bar for oysters and craft cocktails, or grab a seat by the fire pit, with a seasonal menu sourced from the farmers market.
The best burger is at Match Burger Lobster on Riverside Avenue. Shake Shack is the go-to place for teams after weekend games.
New England is known for its chowder, and a local institution is Westfair Fish & Chips. Our choice is the Rhode Island, especially if you're warding off a cold. Taking fish and chips to the nearest beach on a summer evening is a favorite ritual. And Copps Island Oysters are not to be missed.
The best lobster rolls in town are at The Lobster Shack on Riverside Avenue, open year round. Whether you love them hot and buttered or cold and classically dressed, both are equally amazing. They aren't cheap, but boy are they worth it!
The Black Duck is a Westport institution: a beloved dive bar on a converted 1840s barge under the bridge on Riverside Avenue, where you can walk in, drive up or tie up your boat. Come for steamers, lobster rolls and the bleu cheese-stuffed Big Top Burger. Guy Fieri featured it on Diners, Drive-Ins and Dives.
Tacos are not only for Tuesday. Try Hey Taco and Bartaco, where a summer table outside along the river is a local favorite, good for all ages, with the best margaritas in town made fresh to order.
Little Kitchen started as a narrow to-go spot on Main Street and moved to today's location, and it is still the best Asian takeout and delivery in town, maybe in the county. It is as close to New York Chinese as you can get in Fairfield County.
The Blondinit on Church Lane is a family-owned Israeli restaurant serving what it calls Israeli soul food, from falafel and shawarma to shakshuka and baklava pancakes.
Sushi Jin on Main Street is upscale but approachable, with rainbow soup dumplings, a Bluefin Truffle Roll and a sushi counter for custom omakase.
For dessert, Van Leeuwen Ice Cream on Church Lane is the newest scoop in town.
Groceries
An important question: how close is the nearest Trader Joe's? On Post Road East. If you know, you know: seasonal items, great prices and, in our opinion, the best place in town for fresh flowers.
Also on the must-know list: Whole Foods Westport.
For four-legged family members, Earth Animal on Post Road East opened in 1979 as the very first natural health food store for pets, with dog cookies baked in its own kitchen, a Bird Barn and a seasonal backyard farmers market.
The Organic Market has been a local health market for nearly four decades and is the go-to spot for fresh green juice, healthy prepared foods, soup year round and sandwiches. The avocado and cheese with sprouts and cucumbers has been a favorite lunch of ours for over 30 years, and the summer watermelon juice is a must-have.
Bakeries
Fatto a Mano is an Italian micro-bakery for naturally leavened sourdough, focaccia and pastries, and it offers baking classes. Kneads on Riverside Avenue mills its own whole grain flour on site.
Shopping
Main Street shopping runs right along the Saugatuck River: Tiffany & Co., the Chanel Fragrance and Beauty boutique, Rhone, Anthropologie with its home collection, Williams Sonoma, the Serena & Lily home store, Jenni Kayne, Vuori, longtime favorite J.Crew, Rowan, and Bluemercury for cosmetics and perfume. For jewelry, gorjana is my daughter's favorite. Don't miss local artist Kerri Rosenthal, whose joyful paintings and studio shop are a Westport signature.
Out on the Post Road, you'll find Free People, The Toy Post, the go-to for kids' birthday and holiday gifts, from Jellycat and LEGO to a cozy book nook, and 2nd Street, the spot for vintage finds.
Rhone on Main Street has a special place for us. The performance apparel brand was founded in 2014 by the Checketts family, our amazing clients. Read their story in their own words.
Home Goods
Bungalow, downtown, is Wende Cohen's destination for one-of-a-kind home decor sourced from around the world, named the most beautiful store in the state by Architectural Digest. Follow along on Instagram.
You don't have to drive to Vermont to find artisan Simon Pearce's work. His Main Street store offers handblown glass and pottery tableware, lighting and decor, all made by hand in America from the company's roots in Quechee, Vermont, and one of our favorite home gifts of all time.
On the Post Road, Terrain Westport is a local favorite for home gifts, indoor and outdoor plants and table decor. It is the best place for candles and can't be beat for holiday decor in every season, and just being in the store is relaxing. Stay for the cafe set among the plants, and check out its ongoing workshops, including terrariums.
Furniture
The huge Crate & Barrel store on the Post Road is a go-to for furniture, with Pottery Barn also on the Post Road and West Elm on Main Street.
Just over the line, Lillian August has its flagship store on Knight Street in Norwalk. Founded in 1988 by Lillian August and her son Dan Weiss, the family-run business offers furniture, lighting, decor, art, wallcoverings, fabric and rugs, plus design consultations.
Nightlife
The bar at Dandelion, inside the Delamar, is the new place to see and be seen. For a night out with friends, The Clubhouse is relatively new, with golf simulators, karaoke rooms, darts and a full bar and dining room. The calendar stays full, from Westoberfest on Elm Street to summer nights at the Levitt.
Annual Events
Downtown's Westport Fine Arts Festival is not to be missed. Free and rain or shine each spring, it brings juried artists from across the country and beyond, with live music, food and hands-on art for all ages, and it celebrates its 54th year in 2027.
For charity, the Westport Sunrise Rotary's Great Duck Race returns every June. Buy a duck, cheer it to the finish and support local and international causes; the 2026 race raised more than $100,000.
Food lovers mark their calendars for the Taste of Westport, which celebrated its 20th year in June 2026 at the Fairfield County Hunt Club with tastings from invitation-only restaurants and signature cocktails. It sells out every year, and all proceeds benefit CLASP, a Westport nonprofit. In the fall, Westoberfest closes downtown streets for an afternoon of local and regional craft beer.
Notable Westport
Westport is also home to Bridgewater Associates and to the Newman's Own Foundation. Paul Newman and Joanne Woodward called Westport home for roughly five decades, and Newman's Own began here as a salad dressing he created with fellow Westporter A.E. Hotchner.
The town's pull on creative talent continues. Fashion designer Christian Siriano keeps a weekend and summer house in Westport, a modern home near Compo Beach featured in Architectural Digest and Luxe, and he opened The Collective West, his boutique in the center of town, in 2022. Asked at the library's BOOKED for the evening gala how she handles fame, Shonda Rhimes answered simply: "You move to Westport."
Beachside Avenue, along Long Island Sound in Greens Farms, holds some of the most desirable real estate in the county. Phil Donahue and Marlo Thomas, as well as Don Imus, have called it home. In late 2025, five waterfront lots on Beachside, including the estate Donahue and Thomas built, sold for a combined $54 million, the most expensive residential sale in Westport history.
COMMUTE TIME TO NYC
Westport is about 50 miles from Manhattan, roughly an hour to an hour and a half by car. Metro-North serves two stations, Westport (Saugatuck) and Greens Farms, with most peak trains reaching Grand Central in about 74 to 85 minutes.
