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Westport is the kind of Gold Coast town where a riverside library, a summer theater with Broadway pedigree and a sandy town beach all sit within a ten-minute drive. Set where the Saugatuck River meets Long Island Sound, it has drawn artists, writers and actors from New York for more than a century.
The town's roots go back to colonial farming and shipping, and in 1777 British troops landed at Compo Beach on their raid to Danbury, a moment remembered by the Minute Man statue on Compo Road. Later Westport became an artists' colony, and the Westport Country Playhouse, opened in a converted barn in 1931, still stages a full season.
Today visitors come for Compo Beach and Sherwood Island State Park, free summer concerts at the Levitt Pavilion, galleries at MoCA Westport, the shops along Main Street and dinner in the old riverfront village of Saugatuck, all an easy train ride from Manhattan.
Westport's beloved town beach has a long sandy shore on Long Island Sound, a boardwalk, playgrounds, a skate park and grills for picnics. Sunsets over the water draw crowds on summer evenings. Non-residents pay a daily parking fee in season, and weekend lots can close early, so come before 10 a.m.
Established in 1914 as the state's first state park, Sherwood Island has two beaches, open meadows, a nature center and a bird-watching platform over the salt marsh. The 9/11 Living Memorial looks toward Manhattan. Weekday visits are calmer, and Connecticut-registered cars park free under the Passport to the Parks.
Opened in 1931 in a converted tannery barn, this theater has hosted stars from Henry Fonda to Paul Newman, whose wife Joanne Woodward later served as artistic director. It presents plays, musicals and concerts in an intimate auditorium. Book ahead for summer weekends and arrive early to walk the grounds.
An outdoor stage on the bank of the Saugatuck River behind the library that offers dozens of free concerts every summer, from jazz and folk to tribute bands and children's shows. Bring a blanket or low chair for the lawn. Free shows often require reserving tickets online in advance, which can run out quickly.
The Museum of Contemporary Art Westport occupies a renovated building on Newtown Turnpike, with changing exhibitions of contemporary artists, talks, concerts and family workshops. It grew out of the town's long history as an artists' colony. Check the website for current shows, as galleries close between installations.
A bronze minuteman kneeling with his musket stands at the corner of Compo Road and Compo Beach Road, marking where local militia harassed British troops returning from the 1777 raid on Danbury. Dedicated in 1910, it is a favorite spot for photos on the way to the beach. Park nearby and walk to it safely.
Housed in the Wheeler House on Avery Place, the museum tells Westport's story through exhibits on farming, the artists' colony, onion growing and local families, and keeps an unusual eight-sided cobblestone barn. It also leads walking tours of downtown. Hours are limited, so check before going.
A 62-acre nature sanctuary in the north of town with woodland trails, a pond and an indoor center where injured birds of prey and other native animals live. Families come for the animal exhibits and seasonal programs. Trails are short and easy, making it a good quiet hour away from the shore on a hot day.
A former country club on the Sound, now a town park with a public golf course, tennis courts, a pool, a marina and the Longshore Sailing School, which rents kayaks and small boats. The lawns along the water are fine for a stroll. The Inn at Longshore hosts weddings, so weekends can be busy.
The old shipping village near the mouth of the Saugatuck River and the Westport train station, now packed with restaurants, a bridge-side oyster bar and a few small shops. It is a lively spot for dinner after a day at the beach. Walk across the historic swing bridge on Bridge Street for river views.
Downtown Westport's Main Street and the side lanes off it hold a mix of national fashion brands, independent boutiques, bookshops and cafes, with the Saugatuck River just behind. The Parker Harding Plaza lot backs onto the river. Weekday mornings are calmest; weekend afternoons draw shoppers from all over Fairfield County.
A striking modern library on the Saugatuck River with big windows, a maker space and Verso Studios, a recording and video studio open to the public. A grand stair-like forum hosts author talks and events. Visitors can sit with a view of the river and Levitt Pavilion; parking is shared with the Imperial Avenue lot.
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