Westport is a great town for young kids, teenagers and their parents. It’s pretty good for empty nesters too. There are plenty of thngs to do, and plenty of places to do them.
But if you’re college-age?
Hannah Portman — a Westport native, Greens Farms Academy graduate and current Boston University junior — just spent a summer here. She reports:
Many of my college friends didn’t grow up in areas like Westport. Often when I tell them where I’m from, or describe Westport, I can see it register: They realize I’m lucky.
Their first reactions are usually something like, “Westport has the best shopping!” Or, “It’s so pretty there!”
Hannah Portman (2nd from left) and friends, at a Westport 4th of July party.
Having lived here my whole life, I think I started to overlook the great qualities of Westport. I always understood I was privileged to grow up in such a beautiful town. But it wasn’t until I left for college that I truly understood what I had left behind.
I always feel safe here, even walking home from the beach at 11 p.m. I love walking Soundview Drive and saying “hi” or “good morning” to the people I pass, whether I know them or not.
I love how much dedication the town puts into events like the annual fireworks and the various festivals downtown.
The fireworks is one event that draws Westporters of all ages together.
Westport’s sense of safety goes beyond just the physical. It’s a place where people can genuinely be themselves, which isn’t a given in a lot of communities. You can have a protest downtown and it’ll stay peaceful, without fear of violence or backlash.
I think Westport does a great job creating a welcoming environment to all generations. But when it comes to my specific demographic — young adults –there’s still room to grow.
At school, especially in a city like Boston, there’s constant stimulation. Restaurants are open until 2 a.m.. There are late-night spots to hang out, and endless things to do.
There’s always a place to go with friends, an activity to participate in. Of course I don’t expect that same energy from my small coastal hometown. But I do think there could be a bit more.
Main Street has plenty of stores. But Hannah Portman would like to see more variety. (Photo/Hannah Portman)
For example, the cost of a good time in Westport is not sustainable for a college student on their own budget.
It’s always fun to go downtown, do some shopping, and grab something to eat, but every time I do, I spend more than I budgeted. There aren’t any affordable hangout spots. Growing up, places like Rye Ridge Deli and Westport Pizza were cheap, easy options to hang out with friends. Now, it feels like GG & Joe is one of the only spots left with that vibe.
Hanging out — with friends or work — at GG & Joe. (Photo/Hannah Portman)
I often find my friends and I heading to nearby towns like Fairfield, where places like Firehouse Deli and Colony Grill serve as both a spot to eat and hang out.
The same goes for nightlife. Most restaurants close by 11. If you want to be around other 20-somethings you’re going to areas like SONO, or even into the city. Late nights in Westport usually means a backyard, or someone’s car at Compo.
There are ways to make Westport more inclusive and exciting for young adults. The Levitt Pavillion, for example, has so much potential. It’s a great space, right in town, with free shows in the summer. But when I look through their calendar, it’s rare I find something that really excites me.
Most bookings are catered toward adults or children. It’d be great to see them bring in some DJs or indie bands that appeal to my crowd.
A recent Levitt Pavilion audience. (Photo/Susan Garment)
Similarly, the Westport Library hosts great events and speakers, but they seem geared toward older and young audiences. If they brought in authors or creators that my friends and I follow, it could become another draw for young adults, and further differentiate Westport as a cultural center.
I know Westport already offers some leadership opportunities through groups like the Youth Commission and Toquet Hall, but most of these are geared toward high school students. For those who have left for college but still consider Westport home, there’s no clear space to get involved. That’s the gap I’m talking about.
Of course, it’s not all on the town. A lot of it comes down to my generation stepping up. We need young voices in Westport’s leadership that can represent our age group, and work with the programming in the community to help shape a community we want to participate in.
Westport is great, and I wouldn’t want to have grown up anyplace else. There’s so much to love as a 20-year-old, but there’s also room for growth.
The infrastructure is already here. Now we just need representation and initiative to make it even better.
(“06880″‘s Opinion pages are open to all. Email 06880blog@gmail.com. Thank you!)
Hmmmmm; interesting, thoughtful piece. The opening paragraphs surely tip a hat to some positives of growing up in town (especially the “safety” aspect) but seems to me, the specifics relating to college age folks are, accurately, assessed as being quite negative. the surprise is that improving the negatives is only a town or two away. Further, one wonders if Hannah had attended Staples, she would still think people can “genuinely” be themselves…my ear to the ground says, not so much.
Hannah’s ‘06880’ piece from two and a half months ago contributes some of this SHS perspective.
https://06880danwoog.com/2025/06/12/they-started-with-masks-they-end-with-caps-and-gowns/
(Odd that her earlier piece didn’t get a single comment.)
Hannah: you do not need to be part of some formal youth group such as the Youth Commission to suggest or pitch specific ideas for events at the Library or the Levitt (and for those ideas to be taken seriously). If you have some particular authors or speakers or films or performers in mind, by all means go ahead and contact the programmers. My experience has been that they are absolutely receptive to unsolicited queries.
wspt used to be well known for it’s energy, restaurants open and packed until 2 some even 4a only really closing when the sun started to come up, and that included longshore’s restaurant. it’s hard to say ‘who’ (I mean, I could mention some names but don’t want to go there today 😉 flattened it out or when exactly it kind of flattened out but I’d bet it’s got something to do with too much govt & a political party playing ‘nanny’.
Hannah’s nails it. The obvious problem of 20′ and most 30′ somethings simply can’t afford to hang here, eat here, or live here on their own. How do you fix that? One thing that keeps Westport ‘special’ is our zoning regs which is a double edged sword. Practically speaking, zoning keeps Westport a ‘gated’ community. I see changes happening but it will take a generation, Hannah’s generation.
Thank you Hannah, I loved reading what you had to say. You are right on the mark. Don’t stop there, tell us more and help accelerate the changes needed.
I completely agree…..I currently DJ a few nights at The Bridge and Romannaci’s at the weekends (as a bit of side hustle) in Westport and unless you’re prepared to spend a lot of money on cocktails or food… there isn’t really anywhere to to hang out and enjoy more a eclectic or club-like music scene. I’ve suggested DJ nights at the levitt multiple times (which would be a fantastic venue) and because Westport is so well connected in the music scene…we could most certainly attract world class acts through our respective networks and connections. If anyone is interested…drop me a line – philbenjwhite@me.com or visit http://www.bangersmash.live
The demographic that Hannah refers to only resides here, at most, 3 months a year. Who would patronize an affordable “hangout” in February? Or, dance to a DJ at the library in November?
It is a decades long tradition that affluent, well educated people leave their hometown and migrate to a city to experience new cultures and adventures..
The brutal truth is that your generation is “transient” . Simple economics dictates that there are “better “ generations to invest in.You’re lives are at the “fledgling “ stage, the painful transition from child to adult.
Imagine the alternative — a town that did everything it could to keep 20 year olds at home. A lost cause.
Westport has restaurants that are open until 11? Our 24-hour diner closes at 7, 8, or 9, depending on the day of the week!
Post-pandemic, places generally don’t keep late hours. Even in the city, where there are some late options, it seems like most restaurants close earlier than they used to.
(I know that isn’t addressing the demographic-specific concerns, but some of those concerns reflect a broader change.)
Westport’s sweet spot is the K-12 families. When you combine the school system and the town amenities I’m not sure there’s a town in the county that tops it. That drives the housing market.
As you pointed out in your thoughtful post, thankfully bordering towns complement Westport’s strengths so when you’re home from college, you have adjacent options. The SONO economy is driven by shopping and entertainment, and Fairfield has two colleges with year round students so they have bars and restaurants and a concert venue and an in town theater, so both provide all the things you miss from being on campus.
What a pretentious attitude. ‘Didn’t grow up in areas like Westport’? Lucky’?
Chestnut Hill/BC a Green Line stop away. Wellesley to the west, Cohasset to the south, Manchester By The Sea to the north. I get it, all slums.
But yeah, Longshore is a gem compared to ‘The Country Club’.
These are the word of BU students? Not sure any student at BU gives 2 shitz about or knows where Westport Ct. is.
Not sure publicly attacking a 20 year old kid is your proudest moment, unless maybe you’re also one?
She’s not comparing Westport to Boston. BU is a national school and it’s eye opening to many natives when they meet student peers from other parts of the country / world, and reflect on how great they had it.
That’s all this was brother, no need to get all lathered up.
Great post Hannah, my Mom was class of 63, Go Terriers
I’m in my early 60s and also grew up in Westport. Westport is an artistic and well run creative town. It is actually made up of more Jewish people than any of the other towns around them. Hence there was a lot of art theater and upscale restaurants.
But Westport has gone from old money to new money, and the new money is all about putting in sidewalks everywhere, and making sure that everybody can bike everywhere.
Forgetting that this is suburbia and most of us live here because we don’t want to be in a city.
Unfortunately, after Covid, and maybe before it has become completely overrun with elites And is not affordable for even the older people that used to live there. also, the traffic is unbearable. We don’t have the resources to support all the people that have moved here all of the bridges need to be fixed. This is downtown and also on I 95.
The Real estate in Westport has become unaffordable ,which is making it untouchable
Fairfield, which is directly next to Westport has a huge huge college and 20 year-old hang out and opportunities for young people to do fun stuff that they can afford. Norwalk is also right next to Westport. These towns are 5 to 10 minutes away.
Let’s leave Westport alone because it’s gotten way too cityish for the suburbs and too expensive for even the adults to afford
Westport holds many cherished memories for me, and I particularly appreciate observing its continuous evolution. The distinctive character of its shops, restaurants, and beautiful beaches truly distinguishes it from other towns. We are all fortunate to experience the beauty and dedication that Westport consistently offers.