One of the hottest topics in Westport — besides whether you will lose power for a week in the next storm, or merely 3 days — is this: How dead is downtown?
A recent news story caught my eye. According to Destination Development International — a community branding company — in order for a place to be a “true destination,” it must have 10 places that sell food, 10 non-chain specialty shops, and 10 places that stay open after 6 p.m. (“preferably entertainment venues”).
I should mention that I read this story in FairfieldCitizenOnline.com. The piece was written by the president/CEO of the Fairfield Chamber of Commerce, and it declared — suprise! — that Fairfield’s downtown meets those criteria. With “a definitive yes,” in fact.
Fairfield “has plenty of restaurants with varied cuisines and within walking or easy driving distance of each other,” Patricia Ritchie wrote.

With specialty shops, restaurants and entertainment -- plus trees, plantings and benches -- downtown Fairfield is a 10-10-10 destination.
There are many specialty shops too. (“Friends from Westport often tell me there is a noticeable difference between the two downtowns,” she jabbed, “mainly because Fairfield has more independent boutique shops, as opposed to national retailers.”)
Patricia hemmed and hawed a bit on entertainment (“after all, [it] is in the eye of the beholder.”)
But she tossed out an admirable list of places that “one can consider entertainment,” starting with Sportsplex near the train station (fencing and cheerleading lessons, rock climbing, skating, martial arts, laser tag, and god knows what else).
Patricia also cited the Fairfield Theatre Company, with “some of the best bands around.” (Upcoming: Christopher Robin Band, Fishhead Stew, and on February 15: John Mayall.)
The Community Theatre — currently closed — may soon be added back into the mix.
Patricia’s points are well taken. How, then, does Westport’s downtown stack up?
We probably have 10 restaurants, depending on the definition of “downtown,” “selling food” (does Starbucks count?), and “open” (2 new places will arrive this spring on Church Lane, and there’s a vacancy around the corner on Riverside Avenue).
We may reach the “non-chain specialty shop” threshold, again by creative definition of “non-chain” and “specialty.” There’s Sally’s Place, the Liquor Locker — whoops, it’s moving — and, um, of course, well, you know…
As for 10 places that stay open after 6 p.m., offering entertainment: Hah! There’s weekend music on Bobby Q’s roof.
There’s the Y — Westport’s answer to Sportsplex. (For a couple more years, anyway.)
And there is — one day, maybe, perhaps — a movie theater. Like Fairfield, we have a building that’s already served that function for many years. Unlike Fairfield, it is now an upscale hardware store.
Yet Westport does have something Fairfield lacks. It’s not downtown — but it’s showing signs of being a true destination.
It’s called Saugatuck.
There are plenty of restaurants — all within stumbling walking distance — and some have live music.
There are a few specialty shops — you don’t see too many kayak chains around — and the promise of pretty cool entertainment. There’s no Sportsplex or Y, but with the new plaza on the river, and 2 more phases of development to come, there’s lots of room for creativity.
At the risk of incurring the wrath of the Westport Downtown Merchants Association, it seems Saugatuck — with its 10-10-10 criteria — is the new cool spot to be.
Who knows? Saugatuck may even become the next Fairfield.
Hey Dan… The sportsplex in Fairfield has two Westport connections… The Fischels are behind the development of the property and Fairfield Hot Yoga is owned and operated by a Westport Police Officer Rich Failla(sp?)… Sadly Westport is cost prohibitive for the little guys?
Always curious as to why so much of the Westport commercial real estate can remain unrented…
Who owns these strip malls and buildings?
Lower the rents…let them in.
The Westport Library!! Entertainment. Food. Open evenings. Very inexpensive.Beautiful Riverview. Friendly people. Lots of books. The best downtown tradition!
The WestportLibrary!!! Entertainment. Food. Open evenings. Friendly people. Riverview. Lots of books. A downtown tradition!
What about the Westport Community Theatre, Westport Historical Sociey exhibits, Play With Your Food, Westport Arts Center, Farmer’s Market? Much of the content is there….the hype is missing. What we could also use is a town economic development function, which Fairfield has (http://www.fairfieldct.org/ced-ecdev.htm)
Fairfield has always been great and Norwalk is not the slum it used to be, especially South Norwalk. I left Westport in 1978 and moved to Chicago, Rochester, NY and Santa Rosa, CA before ending up in Cincinnati. Although the family businesses are much fewer than they used to be, that is true everywhere in this country. I think Westport has only gotten better and I love to visit. Fairfield County is a wonderful place where almost every town has its own identity. Sadly, such is not the case in the Midwest. On top of the accessibilty of so many great places within a two hour radius, the relatively compressed geography makes it easy to live in one town and enjoy the benefits of others. If I had the chance, I’d return to Connecticut in a heartbeat and having been born and raised in Westport, did not appreciate how well I had it.
What Mr. Woog is missing or purposly ignoring is that Saugatuck and Downtown Westport both fall into the 10-10-10 catagory making WESTPORT the top town in the area. Why he would try and pit one agaisnt the other i am not sure. Main Street and the surrounding areas are full of great stores, a beautiful natural resource in the River and cultrual attractions which rival all surrounding areas. Below is a quick off the top of my head list of the great offerings the downtown area has:
Downtown Westport’s 10-10-10:
Food:
1) Bobby Q’s
2) Spotted Horse
3) Soon to be open restaurant in old Manolo
4) Matsu Sushi
5) Crumbs
6) Westport Pizza
7) Oscars
8) Tavern on Main
9) Starbucks
10) Acqua
(and there are still many more like the Lux Wine Bar, La Villa, Joe’s Pizza, Micheals Pies etc.)
10 Non-Chain Stores:
1) Dovecote
2) Max’s
3) Great Stuff
4) Odds
5)Henry Lehr
6) Spruce Home and Garden
7) Lucy’s
8) Dupont Jewlers
9) The Avenue
10) Spec’s
(and still more i could list like Age of Reason, L’Antiqueer, Suzie Creamcheese, Fridge 125, Go Fiqure, Beautuful Faces, Mixology)
Entertainment Venues (or events)
1) Westport Public Library
2) Toque Hall
3) Westport Farmers Market
4) Westport Country Playhouse
5) Westport Arts Center
6) Bobby Q’s Roof Deck
7) Town Hall (public hearings can be very entertaining)
8) Westport Downtown Art’s Festival
9) Barbecue Blues Festival
10) Levitt Pavillion
(a couple of the above are only once per year but they sure are great, not to mention Aret about Town, Horse drawn sleigh rides, Halloween Parade and more)
So, it is clear from the list above that Downtown Westport is and will always be the 10-10-10 of fairfield county. Better yet, we have a town with 2 great centers thanks to the great job the Gaults are doing in Saugatuck, again setting us apart from every other town in the area. Go Westport!!!!!
PS – We also have some of the best national shopping in the area with stores like Urban Outfitters, Nike, Lux Bond Green, Mitchels, LF, Ther Gap, Banna Republic, Janie and Jack, West Elm, Tiffany’s, Theory, Jack Wills, J Crew, Ann Taylor, Talbots, Patagonia, Restoration Hardware, Claires, Vineyard Vines, Blue Mercury, Ellien Fisher, Brooks Brothers Mens and Womens, Chico’s, Jacardi, Top This, Lulu Lemon, BCBG, Benfit etc, all without a highway like the Post Road running thru it.)
Anonymous, please add the Westport Community Theatre to your entertainment venue list. Actually, they should be near the top.
You consider the Farmers Market, Town Hall, Library and once a year Arts Festival as entertainment? More reasons why everyone goes to Fairfield
Plus not one thing for kids or teenagers to do. Terrible.
There is plenty for kids and teenagers to do, such as:
1) The Levitt
2) The Libary
3) Toque Hall
4) Westport Play House
And the many activites that the YMCA offers
Add Achorn’s, too
your food choices are week. not classy, not nearly as classy as the places Fairfield has to offer.
Fairfield sucks. Downtown sucks. Saugatuck has potential.
So Anonymous, which downtown property do you own?
Oops, wrong place
Love the positive nature of the bloggers on this site. My response to bRA, which i assume means “Big Retarded Ass” is get a life. Without the success of the Downtown and newly revised Saugatuck, our taxes would be the highest in the nation. Westport has so much to offer beyond the commerical developments (like Compo, Longshore, Sherwood Island, Nature Center, YMCA and much much more). Grow up people and begin to appriciate what we have
Give me a break. We would have higher taxes if more people didn’t commute to Westport instead of the city. The town sold out when they let Stauffer Chemical in the ’70’s. Downtown is a corporate dump and in need of repair. Stop calling people names that disagree with you, lard belly.
your jealousy of fairfield is comical. westport is second to fairfield in many aspects.
Beware of wha you wish for. Saugatuck has miserable weekday parking. (Weekends and evenings you can park in RR lots, but that’s a hike for Riversaide Ave.
I have always found it interesting that people don’t deign to walk in Westport. I see people on Main Street circle and circle just to get a space when there are plenty of spaces on the Saugatuck river side. At night, the RR parking lots are empty and people will circle and circle @ Tarry Lodge just to park in their tiny lot. But….. take the train into the city and Westporters will walk for blocks and blocks!!!
Keen observation. As Thoreau said: “One is as lazy as they can get away with.” In my view, they need to ban all cars north of the Post Road downtown and let people walk about. Apparently, they have done that in Saugatuck to everyone’s (?) pleasure.
If you would like a new destination with tons of unique shops and plenty of restaurant choices, take a ride to West Hartford Center and Blue Back Square. As a native of Westport, now living in West Hartford for the past 24 years, our town has that small town feel and a Center that is thriving with activity. There is plenty of parking both on the main streets or in town lots. We have the Noah Webster library, a movie theatre, and about 20 plus restaurants withing walking distance from each other just in the center alone. The stores are mostly independently owned, plus the unique hardware store sellling nuts bolts to dinnerware, and a toy store that kids would love. West Hartford Center is a lot of fun and family friendly. It is only about an hour and a half from Westport. I was in Westport last month and was really dissapointed at the lack of anything to do on Main street and not knowing where to eat. West Hartford has a thriving Center that is well worth a trip for the day. Blue Back is a little over rated but Lasalle Road and Farmington Ave. have all the great places to visit. And if you miss the mall stores, Westfarms mall is only ten minutes away and Nordstroms!
I’m curious, Hope: What effect has Westfarms had on the smaller, independently owned shops in downtown West Hartford?
I think at first when Westfarms opened, it really destroyed the Center, but over the years, West Hartford Center and Blue Back have become a destination spot. I am told a lot of people from the Litchfield area and neighboring states have come to visit and shop. I think since there are tons of restaurants now, that is the big draw also. You will find a lot of young adults in the Center at night going to the bars and restaurants. We now have 3 burger places alone. There is a good mix to choose from. The stores are very high end, so as far as Westfarms, they are getting a different clientele than the smaller stores in The Center. I know the rents are very expensive so of course the merchandise has to be pricey, but somehow it has been thriving and it is nice to walk around. The people are friendly and there is decent parking. It is pet friendly as you see tons of people with dogs around the Center also. We even have a Veterans Memorial Park in the Center. Usually you find kids hanging out there, but for the most part they are respectable of the space. You should take a ride one day and check us out. But don’t come on Monday, for some reason many if not most of the shops are closed that day.
Thanks, Hope. Basically, Westport is the same downtown as it was decades ago. Corporate stores have replaced the Mom/Pop establishments but the lay out is still the same. Plus, much heavier traffic through downtown now on the Post Road. I am always taken back how little the beauty of the water is taken into play in the downtown design. Basically, people parking get the only view. It is too bad for downtown could really be spectacular with the river and all. Someone needs to think outside the box in any future plans.
Saugatuck has some great new business but something has got to be done about the traffic patterns and parking. You can sit forever if you are there between 6 and 8 pm do to all of the cars leaving the station. In addition everyone circles around trying to find parking even though the lower train lot usually has plenty of spaces by 6 or so. Not quite sure what the solution is but something needs to be fixed especially if even more restaurants and shops are going to go in.
After 6 park in the lower lot and walk. For those with good legs it’s not far at all. For those who are more infirm an evening shuttle bus service might eventually work. Before 6 is a different story. There’s been a parking bottleneck near the RR station since the 1950s. When I was growing up in Saugatuck then my parents parked at Peter’s Bridge and then did their shopping on foot — or they deputized me or my sisters and we legged it all the way.
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