Best Walks in Westport

There are plenty of places to take a walk in Westport. Here are five of the best.

The weather is cooling down and school will be here soon, but there are still a few weeks of decent weather left. There are plenty of places to stroll in Westport – from the downtown strip to Compo Beach – and here are some of the best. Some of these are well known. Others lie under the radar of many people. What they all have in common is that they're a relaxing way to spend an hour or two.

Baron's South

You better enjoy this one while you can. A plan to build affordable senior housing on this property, located between Compo Road South and Imperial Avenue, could eliminate these quiet trails. The most common entrance is from behind the Westport Center for Senior Activities at 21 Imperial Ave.

Baron's South is unusual. It's technically a park, but there are no open expanses. Instead, it's a series of steep, paved trails set in a quiet forest. Walkers are rare here, which is unfortunate because the park holds the most random of Westport landmarks. Near the top of the hill rests a stunning, unoccupied mansion. The senior housing plans call for this to be converted into a medical facility, but right now it serves another purpose. The thousands of books to be sold in the Westport Public Library's sales are stored here.

Winslow Park

This park, located across from Baron's South and on the corner of Post Road East and Compo Road North, is perfect for dogs and their owners. You might feel outnumbered if you come here alone. There is a large no-leash area, so dogs are given the freedom they can't get elsewhere. Owners from surrounding towns know place – colloquially called the dog park – as a haven for their pets. There always seem to be more pets than people here.

While the dogs are plentiful, Winslow Park isn't a waste of time for those without man's best friend. There are some nice trails in the swaths of forest, which are popular with joggers. Still, it's known as the dog park for a reason. Bring a dog if you can.


This is the perfect place for kids. The rest of the family will likely have a decent time, too. The wildlife sanctuary on 10 Woodside Lane hosts a variety of exhibits, activities and animals. There's a python, an adorable guinea pig named Puff and a flock of fascinating birds. Admission isn't free, but walking on the surrounding trails is.

There are 62 acres of trails that loop by ponds, brooks and bird feeders. In the winter, cross country skiers use the trails. In the summer, more people should take advantage the land.

Sherwood Island State Park

Walking on the beach is as 'summer' as fireworks and lazy Fridays in the office. Sherwood Island State Park, located at the end of the Sherwood Island Connector, has an impressive beach, but also much more. In one end of the parks, trails cut through the woods. At the others side, beyond the beaches, are trails near the wetlands. Or you can just walk on the beach.

The park is home to Connecticut's 9/11/01 memorial, an understated and poignant reminder of the tragedy from nearly a decade ago. For the kids, the new nature center near the wetlands provides plenty of diversions, from shark dissections to guided nature walks. Unlike the other places on this list, there is an admission fee to get in here.

Leonard Schine Preserve

Out of all of Westport's parks, this one might be the best hidden. Even if you manage to find Glendenning Place off of Weston Road, it's still easy to miss. The small road ends up at the headquarters for Bridgewater Associates, a multi-billion dollar hedge fund. There's no obvious parking for this preserve, so pull over to the side of the road next to the small sign. If you see the building you've gone too far.

The crown jewel is the new natural playground a few minutes away from the road. Small kids will love the handcrafted playground made exclusively from local materials. The park has the rustic appearance of the wild west. Features include an elf village made from acorns, a seesaw made from a plank of cedar and other unique diversions. The trails, while limited, are good way to stretch your legs.


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