After World War II, the housing crunch had young couples scouring the metropolitan area for affordable housing along the three main routes of what is now known as the Metro North transit system. Some of them wound up in this pretty village beside the Saugatuck River, several miles inland from Long Island. Most of the new commuter class found Westport to be too far away from Manhattan (1-1 1/2 hr. each way on the train), and it was deemed the archetype of the far-out bedroom communities that were dubbed the exurbs.
Notable for its large contingent of people in the creative crafts, primarily commercial artists, advertising copywriters, art directors, and their fellows, the town was also appealing to CEOs and higher-level executives, many of whom solved their commuting problem by moving their offices to nearby Stamford. The result is a bustling community with surviving elements of its rural New England past wrapped in a sheen of Big Apple panache.
For more information, visit www.coastalCT.com.
Sherwood Island State Park, Green Farms (tel. 203/566-2305; www.ct.gov), has two long swimming beaches separated by a grove of trees sheltering dozens of picnic tables with grills. Surf fishing is a possibility from designated areas, and the park has concession stands, restrooms, and an amateurish "nature center." The park is open from Memorial Day to Labor Day, daily from 8am to sunset. Pets are not allowed. By car, take exit 18 off I-95 or U.S. 1, following the road called the Sherwood Island Connector. Admission for out-of-state cars from Memorial Day to September is $10 Monday through Friday, $15 Saturday and Sunday. Cars with Connecticut plates are charged $7 weekdays, $10 weekends.
You can get to Sherwood Island by taking a train to Westport and a taxi from the station to the park. If you don't have a car, you might prefer to use that method to get to Compo Beach, the long municipal strand not far from downtown.
West of the town center is Earthplace (formerly called the Nature Center for Environmental Activities), 10 Woodside Lane (tel. 203/227-7253; www.earthplace.org). Its 62 acres offer walking trails, a wildlife rehab center, and a building with live animals and an aquarium. Open Monday through Saturday from 9am to 5pm, Sunday from 1 to 4pm. Admission $7 adults, $5 for children 12 and under.
Rent a sailboat or kayak or arrange a lesson at the Longshore Sailing School, Longshore Club Park, 260 S. Compo Rd. (tel. 203/226-4646; www.longshoresailingschool.com), about 2 miles south of Boston Post Road (U.S. 1). Small boat private lessons are $65 per hour.
One of the oldest theaters on the straw-hat circuit, the Westport Country Playhouse, 25 Powers Ct. (tel. 203/227-4177; www.westportplayhouse.com), had its first performance in 1931. Revitalized under the leadership of Artistic Director Joanne Woodward and other new administrators, the theater produces a full schedule of comedies, dramas, and musicals from mid-June to mid-September, with performances Monday through Saturday evenings and Wednesday and Saturday matinees. There are single-night or short-term events through the winter season as well. Famous, or at least familiar, actors appear in almost every production (Ms. Woodward even persuaded her husband, Paul Newman, to appear in a production of Our Town that went on to Broadway). A music series brings in such acts as Arlo Guthrie, the Preservation Hall Jazz Band, and doo-wop groups. Tickets are priced from about $15 to $48.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.