Discovering Westport

Some people are reaching lots of new goals during Covid-19 restrictions. Starting businesses. Writing books. Founding nonprofits. Me? I haven’t even gone for a run in months. But I do walk. A lot.

Running has been part of my life since I had a crush on a high school boy who was a runner. Don’t judge me. I was a high school girl, after all. More important, I learned to love it. I’m not fast, but I can (or could) run a fair distance. I know this, because I have run the same three loops over and over for years. The benefit of monotony is being able to turn off my thoughts and turn up my music—and know on bad days that I am capable of the distance, as I had done it so many times before.

Then Covid hit, and I didn’t want to run anymore.

Until I get my mojo back, I do realize I should get outside and take short walks at least. As we all know, when we start something, it’s not so bad and we keep going. I tell myself I can stop or turn back at any time. No problem. No guilt. Yet, without fail, I always want to see around the next corner.

That’s how, by slowing down and breaking off my regular route, I discovered three new places to enjoy in Westport. As many years as I’ve been living in, working in or simply enjoying town, I have just not been to some places—not for any reason, except I am usually busy going from Point A to Point B in my loop. Maybe it’s the same for you? Here are three unexpected yet welcoming paths I found while wandering.


Baron’s Estate South. If you’re like me, you’ve passed the property thousands of times and wondered about it. It belonged to Baron Walter Langer von Langendorff, who made his money in perfume. Do you recall White Shoulders? It was created here, according to a 2013 Westport News article. I learned that his estate is twenty-three acres in the center of Westport; I discovered for myself that it affords impressive views of downtown. The baron also owned what we call Winslow Park, another thirty-two acres. Both are walkable, but I had overlooked the south side, possibly because it feels private. The 1959 brick mansion simply sits there, year after year. It once had gardens and a greenhouse; the tiered garden steps are still there. Its purpose now is as a time capsule and peaceful retreat within walking distance of the Post Road. If only it were a town building for events—take a look one day and imagine the possibilities. Currently, the path around the property is hilly, curvy and unkempt—returned to nature. I love it, but It is not suited to anyone with a physical disability and not for kids. This place is best for dreamy alone time or private romantic strolls for those with a poetic eye.


Sherwood Island. Everyone knows this landmark. It’s vital to Westport. It’s popular. It’s beautiful. So why had I been there only once to see the 9/11 Memorial? I once again blame routines. I simply never thought to go, yet I was missing out on a local treasure. One day this winter, I decided to check it out. I was not alone—plenty of cars in the parking lot—and I randomly started walking to the right, toward the shoreline. I had abundant social distancing, start to finish. Everyone, from young families to chatting power walkers, seemed to enjoy the peace and quiet. I strolled the beach as seagulls glided in the breeze overhead and soon came across the most striking view of Compo—striking because it was such a surprise. I’m not sure why it should be, but it was refreshing to see the familiar from a new vantage point. It won me over. I was able to take in this beautiful neighborhood from a new perspective, and, yes, it still has its balance of charm and sophistication. The walking loop continues to a flat path that runs along Old Mill—and would make a great addition to an easy-going run.


Levitt Pavilion. I know the Levitt for its concerts along the water. It’s where I met Michael McDonald and danced to Huey Lewis and The News (and handed him the world-traveling Flat Stanley on stage—a story for another day). But mid-winter, the stage is cold and closed, which makes it the time to wander and explore while practicing social distancing. I have always enjoyed the little bridge between the library and the back parking lot of the Westport Women’s Club, probably because it feels off the beaten path (though, of course, it’s not). Then I noticed to the waterside of the bridge, the walk behind the stage. Again, clearly meant to be enjoyed and I had just never done it. Now with time on my hands, I did and discovered another wonderful surprise. It affords wide-open, lovely views of the river and the bridge. It is short and flat, making it appropriate for most people—especially those who enjoy a different perspective on where they live.

Have a great walk for me to try in Westport, Weston or Wilton? Let me know! Diane.sembrot@moffly.com

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