Cub Scout leader James Delorey writes:
At this year’s Soundview Stroll, Westport Cub Scout Pack 39 asked strollers: “What do you love about Westport?”
If a stroller took a moment to talk with a Cub Scout or Scouter, we asked them to help us discover the places that make Westport special.
We brought them over to a huge map, from the town’s Engineering Department. It includes every road, street, property lot, park, school and geographic feature in town.
Offering 6 different colored markers, we asked people to share: Green for your favorite place to explore nature. Blue for your favorite place to play. Yellow for your favorite place to eat. Purple for a favorite place to walk, bike, or hike. Orange for a place to have fun with your friends. And draw a red heart over “a place that makes you proud of Westport.”

Cub Scouts and strollers at the Soundview Stroll, with their map.
Soundview Strollers of all ages took a moment to orient themselves on the map. In this age of Waze and GPS navigation, we learned that there are many young Westporters who have never looked at a paper map of their town.
Then there were directionally gifted people who thrilled at their fluency with maps, and the chance to help the lost find their way to their favorite places.
Our map came alive with color – dots and red hearts. Runners and bicyclists drew long purple lines for their regular routes. Students drew hearts over their pre-schools and elementary schools, and orange and blue dots over the playgrounds where they play and have fun with their friends.

The Cub Scout map.
Dots for “favorite place” to eat were hungrily drawn for Old Mill Grocery, Bartaco, Casa Me and the Black Duck (one of the most fun spots to find on the map – tracing the Saugatuck River until you’re just under “Interstate 95”).
Longshore, Old Mill Beach (with dots and hearts going all the way out to the sandbar!), Sherwood Island State Park and Burying Hill Beach – Westporters love to get outside.
Intrepid explorers put green dots on the Caryl & Edna Haskins Preserve and the Children’s Natural Playground at Schine Preserve – a couple of Westport’s hidden gems (great places to explore nature).
On our map, Compo Beach is chaotic with color. Multiple blue dots – favorite place to play – were turned into a smiley face by one clever contributor. Red hearts are all over the place (“A place that makes you proud of Westport”).

The Westport Rotary Club’s lobster — aka Rick Benson — chose Compo Beach as his favorite spot, presumably for LobsterFest. The annual event — a favorite of many residents — takes place Saturday.
Our Soundview Stroll map station was really a bit of intelligence gathering. What lights up people’s faces?
Kids love thinking about the places they play, explore nature, and have fun with their friends. Parents loved seeing the places their kids chose, and how they talked about them. The whole exercise was really about starting a conversation.
And we were listening!
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Tomorrow (Friday, September 18) is “Scouting Day in Westport.” Cub Scouts Pack 39 invites all boys and girls from kindergarten to 5th grade (along with parents and siblings) to join us at Compo’s South Beach (the far end), starting at 5 p.m.
Meet new friends, make s’mores, enjoy a campfire, hunt for crabs.
And, if we’re lucky take in a well-earned sunset!
We’ll try to answer any questions you have about Scouting in Westport. But we want to hear about what you’ve discovered too.

Cub Scout Pack 39 makes s’mores at Compo, last year.
We’ll have our giant town map and our markers. Let’s share what we love about Westport, and the wider world.
Cub Scouts explore nature, play, eat, walk, bike, hike, and have fun with friends. We hope you’ll join us.
(Westport Cub Scout Pack 39 is celebrating its 75th year of Scouting. We welcome all boys and girls, kindergarten through 5th grade. To learn more, click here.
(“06880” regularly covers youth activities in Westport — and all the places mentioned here. If you share our love for this town — and this blog — please click here to support our work. Thank you!)

Westport is amazing, geographically desirable, incredible restaurants, philanthropic people, top high school, great kids, and the negatives are minor and easy to fix
1) traffic needs to have a few intersections open up lanes take out a few buildings.
2) third world mta train system need to bludgeon the state reps until they do something, 80-90 minutes to go 40 miles to nyc is a joke
3) every board meeting in this town remove chairs. Nothing gets done ever. Hours of pontificating with no result. An old arthur blank hme depot founding trick. Remove chairs and watch how fast things get done. Sidenote i wanted to put beautiful benches at 9/11 memorial and veterans park in town with cement pad installed all no cost to town and state. I need monrhs of meetings and approvals, so walked away.
Last time I checked, just now, metro north schedule to GCT is about 75 minutes. As it always has been.
The GCT evening express to Westport is 65 mins. MNR slowed the trains after the 2013 Spuyten Duyvil derailment, before then the fastest evening express I remember was 57 minutes.
So you’re not wrong, trains are slower, but it has to do with the all the curves in the tracks which date back to the Revolutionary War, and not the quality of the train car itself. If you’ve ever taken the Acela from NYC to BOS you notice the slow speed in much of CT. I don’t think straightening the track will ever happen.
I see what I love about Westport every time I look in the rear view mirror.
Eric- and here we were thinking you were pining for the old place seeing as you are here every day seemingly desperate for news.
I think everyone should be able to post their opinions, even if the majority of readers don’t like one’s opinion. As long as one isn’t being rude or insulting. Now, there are so many great people in Westport and no doubt it’s loved by everyone who lives there! With that said, there are negative aspects of it too. Once a Westporter, always a Westporter! Remember that quote.
Adrian,
Sadly the internet is full of negative trolls ! #smh
I will echo James’ sentiments, in that Westport has been a terrific place for our family to set down it’s roots.
Our quality of life in Westport is pretty fantastic. From the wonderful neighbors we enjoy, to the town’s location on the water, to the proximity to fun local places to eat – nothing can beat takeout at Burying Hill beach, walking with friends, hidden parks to explore, fishing off Cockenoe Island, schools filled with learning and fun activities with caring teachers, staff, and volunteers. We have the verdant expanses of space at Earthplace to explore and animals to learn about, the amenities at the Y and more importantly the fabulous members we encounter there. (Plus, I can get delivery of most anything I want in 2 days, whereas my sister in Vermont can wait up to 2 weeks!)
The traffic isn’t great, but we’re a victim of our own success in being where so many people want to live. It is a reflection of the privilege we have in our lives, which we can’t take for granted.
Elizabeth, I’m a Westporter as much as anyone living in Westport now. That’s because once you’ve lived in Westport, you’re a Westporter for life. My time / association was 1947 to 1993. Like Scooter or Eric, once you’re a Westporter, you’re always a Westporter. My family goes back 123 years and my father was born in a farmhouse in 1918! My philosophy is, if you moved here 3 years ago, or 25 years ago, you’re a Westporter and will always be one! For years on this blog I have maintained that philosophy. If you moved here three years ago, and you move away, you’re still a Westporte for life! That connects us all- forever.
After thirty+ years here, I’m pretty sure the thing I like most about Westport in 2026 is how easy it is to get elsewhere.
Amtrak can easily get you anywhere from Boston to Washington. There is probably no better place than NYC to catch flights to any place in the world.
Good access to world class culture, entertainment, sports, and restaurants in New York. Concert venues in Connecticut have improved a lot the last three decades – and the aforementioned NYC is easy to reach.
I spend less and less of my money in Westport, because downtown is like a mall and restaurants are hit and miss. Without children in schools, my personal priorities are treated as afterthoughts by those who would otherwise have their hands out for my tax money. And the Post Road traffic! Also, the Town is dead after about 9:00.
Okay, so I need to name something specific – I love Athletic Shoe Factory, which offers extremely great service. And anymore, if I want to eat out here, I like Hudson Malone with its good food and great service. Fatto a Mano!
I’ll probably keep Westport as a “home base” until they cart me off in a pine box. But mainly because of the location.