Top Outdoor Activities in Westport

Few places along Connecticut's Gold Coast showcase the region's best-of-all-worlds natural beauty better than the town of Westport. Equal parts coastal enclave and rural retreat, with a vibrant town center along the Saugatuck River in between, the promise of an active, high-end lifestyle permeates throughout. With its vast waterfront, picturesque parks, and a wealth of outdoor recreation, Westport is the perfect place for homeowners and visitors alike to enjoy a number of outdoor pursuits.

For those who crave the sand and sea, Westport offers several pristine beaches that provide the perfect setting for relaxation and recreation. Compo Beach, a beautiful 29-acre beachfront, is one of Westport's most beloved destinations. Visitors can enjoy a morning walk along the shore, casual sunbathing, or an evening picnic with a view of the Sound. It's also an excellent spot for paddleboarding, kayaking, and beach volleyball. Additionally, Compo Beach is home to a well-maintained Skate Park, a wonderful place for skateboarders to hone their skills in a scenic outdoor setting.

For those seeking a quieter beach experience, Burying Hill Beach offers a more secluded environment. This small yet picturesque beach is ideal for those who enjoy a peaceful day by the water, collecting seashells, or simply taking in the stunning coastal views. Old Mill Beach, located near the Old Mill tidal inlet, provides another tranquil option. With its charming waterfront homes and gentle waves, Old Mill Beach is perfect for a relaxing afternoon by the water.

The Saugatuck River provides a scenic backdrop for kayaking, paddleboarding, and leisurely boat rides, while the greater Long Island Sound opens up a world of sailing and deep-sea fishing opportunities. Cedar Point Yacht Club, at the edge of Bluff Point on Saugatuck Island, and Saugatuck Harbor Yacht Club tucked in behind Driftwood Point, are known for their world-class regattas and sailing programs and offer prime spots for those looking to refine their sailing skills or dock their vessels in an exclusive setting.

Public sailing opportunities are found at Westport’s two marinas, and the Saugatuck River Boat Launch, with private yacht charters also available for those seeking a more luxurious boating experience along the coast.

Longshore Club Park is one of Westport's most treasured amenities, offering an array of outdoor activities.The 18-hole Longshore Golf Course and driving range, with stunning water views, provide an excellent playing experience for both casual and avid golfers. In addition to golf, Longshore boasts tennis courts, multiple swimming pools, and the Longshore Sailing School, making it one of the most well-rounded outdoor destinations in town. Whether perfecting your serve, going for a refreshing swim, or enjoying a sunset dinner at its waterfront restaurant, La Plage, Longshore embodies the sophisticated recreational lifestyle Westport is known for.

Westport is home to several outstanding tennis facilities that cater to players of all skill levels. Longshore Club Park boasts nine tennis courts and two pickleball courts, Compo Beach has two asphalt pickleball courts, while the Town Farm Ball Complex includes four tennis and four pickleball courts. And though a private golf and social club experience is the primary draw at Birchwood Country Club, the club’s exclusive Racquets Membership option may feature the best racquet sport experience of all, with seven tennis courts, three pickleball courts, and two lighted paddle ball courts for member and their guests to enjoy.

The best encounters with Westport's natural beauty occur when traversing its hiking trails and preserved woodlands. Sherwood Island State Park, Connecticut's first state park, offers a mix of sandy beaches, salt marshes, and scenic trails.

Ten minutes north of Sherwood Island, in the heart of Old Hill, you'll discover Earthplace, a 60-acre wildlife sanctuary that provides a more secluded hiking experience. With its winding forest trails and interactive nature center, Earthplace is an excellent escape for those who appreciate a more immersive connection with nature.

For road cycling enthusiasts, Westport offers some of the most scenic and enjoyable routes in Fairfield County. While one can blaze their own trail across town, the neighborhood of Greens Farms promises cyclists some of the Gold Coast's top routes. Green Farms Road and Beachside Avenue both feature quiet, winding roads lined with historic estates and waterfront views and serve as Westport's link in the 3,000 mile East Coast Greenway.

Equestrian enthusiasts will find Fairfield County Hunt Club a premier destination for horseback riding. Offering riding lessons, show-jumping competitions, and polo events, this exclusive club provides seasoned riders and beginners the opportunity to enjoy the sport in a refined atmosphere. The club's beautifully maintained grounds (you can also partake in tennis and swimming here) and high-caliber equestrian training make it a staple of Fairfield County's elite outdoor scene.

For those who enjoy connecting with nature in a low-impact, hands-on way, the Westport Community Gardens provides an excellent opportunity to grow fresh produce while fostering a sense of community. Located adjacent to Long Lots Elementary School, these well-maintained gardens offer residents the chance to cultivate their own fruits, vegetables, and flowers while enjoying the beauty of Westport's green spaces.

The Westport Farmers Market is also a must-visit for those who appreciate fresh, locally sourced food and unique crafts. Held weekly—the summer market is outdoors in Westport Village at Imperial Avenue and Thomas Road—this lively market features seasonal produce, artisan foods, and handmade goods from local vendors. It serves as a vibrant gathering place for residents, offering a perfect way to spend a morning outdoors while supporting Westport's thriving agricultural and artisanal community.

Nestled along the Saugatuck River just behind the Westport Library, Levitt Pavilion for the Performing Arts is one of the town’s most beloved summer destinations. This open-air amphitheater offers a packed calendar of free outdoor concerts, cultural performances, and family-friendly events under the stars. From local bands to nationally touring acts, Levitt is the perfect spot to spread out a blanket, enjoy a picnic, and take in live entertainment with a riverfront view. Whether you're a music lover or simply looking for a unique way to spend a summer evening outdoors, Levitt Pavilion delivers an unforgettable Westport experience.

Located across from the Westport Country Playhouse, Winslow Park is a favorite gathering place for Westporters and their four-legged friends. This scenic green space features winding trails, wide open fields, and a popular off-leash dog area, making it ideal for morning walks, casual jogs, or a relaxed afternoon outdoors. Shaded paths and benches invite lingering, while seasonal events occasionally bring added energy to the park. Winslow strikes the perfect balance between nature and community, offering a low-key yet beloved way to enjoy Westport’s outdoors.

Whether you're a local resident or considering making Westport your home, the town's access to outdoor amenities makes it an ideal destination for those who appreciate nature, recreation, and a strong sense of community.

If you're ready to discover more about luxury Westport homes, contact Cindy Raney & Team today to start your Gold Coast real estate journey.

_{*Header photo courtesy of Discover Westport}