Downtown Westport Taken Over By Scary & Adorable Trick-Or-Treaters!
Photos and Story By J.C. Martin For WestportLocalPress.com Click on an image to enlarge and open gallery.
One of Westport's favorite family events, the annual Halloween Parade on Wednesday, October 2th was a great success as hundreds of children and many costumed parents swarmed downtown merchants, eagerly seeking to fill their bags and buckets and sacks with as many treats as they could provided by the generous Main St. merchants who welcomed them again this year.
Westport PD Corporal Craig Bergamo about to lead the official start to the Parade as the crowd lines up at the Post Road and Main Street.
They were all there; cowgirls and Ghostbusters, pirates and football stars, Buzz Lightyear who stopped by before going to infinity and beyond and even a giant brown dog who cleared a path everywhere it went.
Photos and Story By J.C. Martin For WestportLocalPress.com Click on an image to enlarge and open gallery.
Whether they walked, ran, toddled or swung from tree-to-tree as this intimidating ape did, or were wheeled in the many strollers, the crowd was delighted to be there as were the merchants who had the happy task of sharing the joy that Halloween brings each year.
Harris Falk stood out even among this throng of very noticeable characters as did the big brown dog who seemed to be everywhere, and the traditional Halloween black cat as she wheeled a junior sized Spiderman up Main Street.
After Their March Up Main St.Families Headed Over To Veterans Green Where A Big Party Was Already Underway
For the first time Westport Parks & Recreation invited noted children's entertainer The Amazing Andy who has been thrilling audiences for over 50 years with his magic, juggling, balloon artistry and more. Andy lived up to his name and then some as he had the children mesmerized with his performance.
Andy's performance was often interactive, engaging the children and involving them in his show. He had them laughing and cheering and completely charmed. One lucky young audience member was invited up to join in his juggling, catching on of the juggling clubs to the appreciation of the audience.
Andy involved many members of the audience, keeping them engaged and enjoying participating in his wonderful performance.
For his finale, Andy took again delighted the audience by producing from his “trick box” Cohan, his beautiful 15 month old Netherlands Dwarf rabbit and afterwards children and a few adults eagerly lined up to pet this calm and gentle beauty. The joy on their faces was clear as they gave Cohan some love.
Another big moment of the day was the appearance of much loved celebrities, The Addams Family who were a big hit. The Tierno family got lots of attention with Chris presenting a great Gomez with wife Nicole stunning as Morticia. Gigi portrayed Wednesday Addams to perfection and Luca Tierno gave us a memorable Cousin Itt accompanied by “Thing”.
Westport Volunteer EMS was on hand as always, represented by Abby Guadron, Steve Navarro, Maddie Sine, and Lisa Buckland and a patient” of unknown condition examined by a somewhat questionably medical practitioner. Kids were invited to see the inside of the EMS ambulance and receive more treats.
Westport Police officers were on hand , enjoying the day and offering a buffet of goodies.
First Selectman Kevin Christie took a moment for a photo op with Westport Firefighters Liam Chrzanowski and Shareef Conjura.
DJ Shuttle, a New York City-based DJ, producer, and remixer known for his custom R&B, hip-hop, and house music blends, as well as classic old-school sing-alongs kept the party jumpin’ and brought one woman to create her own dance floor, enjoying the tracks as the afternoon was concluding.
It was another great Halloween family day in Westport as families chatted and children played all dressed up in their myriad of costumes.
Spooky Stroll Will Take Over Downtown Westport On Wednesday
On Wednesday, October 28th Downtown Westport will be overrun with the cutest, scariest and most adorable children, both younger and older as one of Westport's favorite family events, the Westport Halloween Parade again returns to town. Weather looks to be good so far, but a rain date is scheduled for the next day, October 29th.
Photos of 2025 Halloween Parade by J.C. Martin for WestportLocalPress
Each year, hundreds enjoy this event held by The Westport Parks & Recreation Department, in conjunction with the Westport Police Athletic League and the Westport Downtown Merchant’s Association. Several roads downtown will be closed prior to the start of the Parade.
Westport Police Department has issued this Traffic Advisory:
- Main Street will be closed from Post Road East to Avery Place starting at 2:30 p.m.
- Avery Place will be closed starting at approximately 3 p.m.
- Myrtle Avenue from Evergreen Avenue to Main Street will be closed starting at approximately 3 p.m.
Access to early voting at Town Hall will still be accessible.
All roads are expected to reopen by 6 p.m. Motorists should expect delays in the center of town due to these closures. The police department asks that motorists use extra caution when driving through the area.
Spectacular Hunter's Moon Sunday Night
Hunter’s Moon photo by J.C. Martin, edited with AI.
According to the Old Farmer's Almanac, October's full moon is known as the Hunter's moon, as it rises near the time when farmers have harvested their crops in their fields, enabling hunters to more easily track game for winter food. It is the full moon immediately following the Harvest Moon which was on September 26, which is the full moon closest to the autumn equinox, the start of Fall. It rises earlier and brighter in the evening, lending extra light to the fields and forests.
Although this moon appears larger than usual it same angular size as when it appears directly overhead This phenomenon is called the "Moon Illusion," causing us to think that the moon is larger than it is while close to the horizon.
WestoberFest Draws Biggest Crowd Ever!
Photos And Story By J.C. Martin For WestportLocalPress.com Click on an image to enlarge and open gallery.
The ninth annual WestoberFest organized by Westport Downtown Association drew its biggest crowd ever to Elm Street on Saturday, October 3, 2026. The great attendance occurred even though there were two other major events in Westport that same day and time, Earthplace Fall Fest and the Slice Of Saugatuck.
Attendees were able to sample craft beers for every palate with over 20 breweries and more than 50 local and regional brews available to enjoy. There was a nice selection of foods as well including the Blind Rhino food truck.
Entertainment included the first ever hosen-off, which gave men the stage to strut in their finest lederhosen.
Photos And Story By J.C. Martin For WestportLocalPress.com Click on an image to enlarge and open gallery.
One Bad Oyster again performed on stage after being a big hit at last year's event.
Lonnie Quinn returned for the third time as host and emcee and his duties included running the "balance your beer stein" competition.
Three brave women took took up the challenge performing a variety tests of balancing a beer stein while making different moves designed to force one to spill their beer. It came down to two contestants who displayed great balance and flexibility and were able to hold their beer steady for each test creating a tie.
Photos And Story By J.C. Martin For WestportLocalPress.com Click on an image to enlarge and open gallery.
The crowd was focused on every move of the "balance the beer stein" contest, waiting to see who would prevail.
In the end the winner was decided by which of the two contestants could chug the full stein the fastest. Lily Williams from Maine, blue cap who was visiting family in town showed her chugging ability was on par with her balancing skill and raised her empty stein in victory.
Photos And Story By J.C. Martin For WestportLocalPress.com Click on an image to enlarge and open gallery.
This year, Westoberfest partnered with 3 art schools providing games and activities for the whole family. We’re not sure who came up with the “throw the ball into the pot”, but it WAS popular!
Photos And Story By J.C. Martin For WestportLocalPress.com Click on an image to enlarge and open gallery.
No matter what event we cover in Westport, there is never a shortage of awesome four-legged attendees.
The magnificent canine at the right is a long haired Akita, a Japanese breed which once guarded royalty. The can cost from $1,000 to $2,000 or more, yet this beauty, who was certainly a center of attention, was actually a rescue who had spent some time living on the street.
Photos And Story By J.C. Martin For WestportLocalPress.com Click on an image to enlarge and open gallery.