Attractions
Westport Country Playhouse
The Westport Country Playhouse epitomizes the town’s long passion for the arts, and its embrace of artists. Founded in 1931 in a former tannery by famed producer Lawrence Langner, it was one of the first summer stock theaters in the country. Drawing stars like Henry Fonda, Olivia de Havilland, Eva Gabor, James Earl Jones, Eartha Kitt and Liza Minelli, it has long served as a testing ground for future Broadway shows, a venue for favorite revivals, and an inspiration for theater-goers of all ages. Stephen Sondheim once apprenticed there! In 2005, Joanne Woodward helped spearhead a $30 million renovation that turned the venerable red barn into a year-round theater. “The Playhouse” is truly one of Westport’s crown jewels.
Westport Library
From humble beginnings in 1908, the Westport Library has grown to become one of Westport’s most beloved and eclectic institutions. Relocated to the banks of the Saugatuck River in 1986, the library recently tackled a transformation project that has created a model for libraries everywhere. With enlarged MakerSpace, a new Hacker Space, a flexible “Forum,” a recording studio, special spaces (and librarians) for children and teenagers, expanded meeting rooms and a healthful café, the library is well designed for the 1,700 lectures, discussions and concerts it offers each year. Users enjoy spectacular river views. They can even sit outside, on the enhanced Riverwalk. The renovation has transformed not only the library, but all of downtown.
Longshore Club Park
In 1959, the private Longshore Club was about to be sold to a housing developer. In just 19 days, Westport officials bought the property for the town. Today, Longshore is a 168-acre recreational, entertainment and social center. A newly renovated 18-hole golf course, tennis and paddle board courts, two swimming pools, and sailing school with boat, kayak and canoe rentals are just a few of the draws of this gorgeous waterfront park. In the winter, skaters enjoy an outdoor rink. Diners flock all year long to La Plage, the signature restaurant. The adjacent Inn at Longshore is a perfect venue for weddings and other celebrations. Very few towns have a municipal country club, none have one like Longshore.
Levitt Pavilion
Every summer for more than four decades, the Levitt Pavilion for the Performing Arts has entertained Westporters and visitors with over 50 nights of entertainment. Rock groups, comedians, folk singers, jazz musicians, children’s performers, military bands; you name it, they’ve played the handsome stage on the banks of the Saugatuck River. Each night, hundreds of folks relax on the grass, enjoy picnic dinners, and leave with smiles. Amazingly, it’s all free. Except, that is, for one special fundraiser each year. Headliners have ranged from John Fogerty, Ray Charles, Willie Nelson and Frankie Valli to Orleans, America and Buckwheat Zydeco. See you at the Levitt — don’t forget your dancing shoes!
Fairfield County Hunt Club
In 1924, the family that founded Pepperidge Farms bought land on Long Lots Road. They offered it to a fledgling horse club, which sponsored polo, shows and hunting. Nearly 100 years later, the 40-acre property includes six barns, two outdoor riding rings, two indoor rings, eight tennis courts, four paddleball courts, two swimming pools, a formal dining room, a casual grill room, and a 60’ x 120’ skating rink. Hunt Club members include plenty of avid riders and other young families, who appreciate its lowkey vibe, modern amenities, and many opportunities for fun.
Winslow Park
First it was the site of the stateliest homes in Westport. Then it was a sanitarium. When B. Altman wanted to buy 22 acres near downtown for a department store, municipal officials bought it instead. Their foresight was impressive. Today, Winslow Park, named for the family that owned that original mansion, is open space. It’s filled with walking trails, bike paths, a picnic area, and plenty of meadows and woods. That makes the land itself perfect for dogs and dog lovers. There’s even an annual dog festival there each May. Which is why you won’t hear Westporters call it “Winslow.” It’s always “the dog park”. Arf!
Saugatuck Rowing Club
An old freight station on the Saugatuck River was the perfect place to store rowing shells. That’s how the Saugatuck Rowing Club began, 30 years ago. In the years since, it’s churned out some of the top racers in the country. SRC’s highly regarded youth program draws boys and girls from across Fairfield County (early competitors included the Winklevoss twins, of Facebook fame). Rowers of all ages train on the river, all year long and in all conditions. Non-rowers flock to the club too, for its fully equipped fitness center, and second-floor restaurant and deck. Both the fitness and dining facilities have views of the river, and the rowers that you can’t find anywhere else.
Staples High School
When Horace Staples started a school in 1884 with a graduating class of six girls, he could never have imagined what it would become. Today, Staples regularly leads surveys of top high schools in the country. With an astonishing array of AP and honors courses, professionally equipped culinary kitchens and TV studios, dozens of electives, a robust senior internship program, nationally recognized drama and music groups, consistently high-level sports team, and an innovative Pathways school-within-a-school, Staples is a primary draw for families considering a move to Westport. Check out the newly renovated, three-story “Home of the Wreckers” for yourself!
The Stations
The railroad has been the lifeblood of Westport since the mid-1800s. Originally carrying goods from factories and produce from farms, today it ferries commuters every morning to New York, and brings them back at night. It also provides easy access to the city’s museums, theaters and other attractions (like Yankee Stadium, the MoMA, etc.) for day trippers. Others take the train to Stamford, New Haven and nearby destinations. Westport has two train stations. The larger one is in Saugatuck. It’s across from Railroad Place, with one-of-a-kind, locally owned coffee shops, restaurants and stores (plus unique Donut Crazy, on the other side of the tracks). The smaller one is in Greens Farms. Both offer yearly permit parking, along with day rates.