Downtown Westport
Westport’s downtown area is the heart of a special community. Out of a 1920’s picture postcard Main Street hasn’t changed until recently when the national chains moved in.
Let me tell you what it was like and how the spirit lives on. At the top of the street was the Old Remarkable Bookshop. Painted pink it was a landmark for over 50 years. Here you could meet authors like Robert Mitchum and M. Scoot Peck who wrote the Road Less Traveled. It was a great place to kill some time before Boarders and Barnes & Noble squeezed them out.
There are however some steadfast mom and pop business that have weathered gracefully with each passing year. Oscars delicatessen is located two doors down and has been a staple since the 1940’s. Westport Pizza owner Mel Mioli has feed many generations of Westporters the best tasting pizza.
A local grocer, Gristedies was the most fantastic place to have a house charge. They’d bill you monthly for your fresh vegetables, fish, and meat. The closest thing to this nostalgic experience today is Calises Market where Paul Newman used to get his meat from the butcher. Tavern on Main use to be Chez Pierre and the ambience hasn’t changed in over forty years. The only thing I can think of is that the colonial fireplace now gas operated.
Walking down Main Street as a long time resident and witness to change one can still feel grounded by these recollections and memories. This is what makes Westport so special for so many people. Not only the legacy residents but also the newbie’s too.
The community thrives year round on Main Street. Boy Scouts, Girl Scouts, High School raffles and fundraisers can be seen most weekends dutifully raising money for good causes.
The annual Sidewalk Sale in June and the Art Festival in July are events not to be missed. The kids always look forward to the annual Halloween Parade where they can be seen happily marching up the street to Town Hall collecting treats from the local merchants along the way.
To nurture your cultural needs the downtown area comes alive. The Westport Playhouse Theater renovation was spearheaded by Paul and Joanne Newman to the tune of $35M. There are weekly performances and a summer season stock series of plays that gain national attention.
Just a stones throw away from the Playhouse is Winslow Park, which is the designated area for dog lovers and walkers. Here you can throw a Frisbee and mingle with other dog owners. The park was the former property of the Baron Von Langendorff the perfume magnet. His mansion still stands across the Post Road behind the newest bank in town.
The downtown area including Main Street offers the local residents a unique small New England town lifestyle, where you can walk to everything you need. If this is important to you; then this is a neighborhood worth looking into.
If you’re considering Westport as a community to live I’d love to share my passion, knowledge and experience with you. Please feel free to call me at 203-814-6100 or email me at livingwestport.com to set up an appointment so you too experience the allure of this special place so many of us are proud to call home.

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