Community Corner
🌱 Patch AM: Westport's Superintendent Of Schools Wins National Awards
Be sure to catch Whale of a Sale on the Westport Patch calendar

Greetings Westport! We're your go-to source for what's happening in town. Read on to get plugged in! ☀️
In today's newsletter:
- National honors spotlight leadership in Westport's public school district
- Everything Westport voters need to know before casting ballots Nov. 3
- How much harder is it to retire comfortably in Westport now?
Also on today's calendar: Whale of a Sale and 27 more events.
Today's riddle: How do billboards talk? 🤔 (Answer below!)
- Saturday: Sun through high clouds, with a high of 67 and low of 50 degrees.
- Sunday: Some rain in the afternoon, temps: high: 65, low: 58.
- Monday: A couple of morning showers, with a high of 71 and low of 53 degrees.
📰 News we're reading
1. Westport's Superintendent Of Schools Wins National Awards (patch.com) — Westport residents can celebrate Superintendent of Schools Thomas Scarice, who has earned both the 2026 Superintendent of the Year Award and a national Technology and AI Award. Local education leaders say the honors reflect his leadership of Westport Public Schools, especially his focus on student outcomes and responsible use of artificial intelligence while keeping human connection at the heart of teaching and learning.
![]()
2. Westport 2026 Election Voter Guide: Candidates, Voting Information (patch.com) — Westport voters will head to the polls on Nov. 3 to choose candidates for governor, Congress, and several key state and local offices, including state senator and representative. The guide explains polling hours, early voting at Town Hall Auditorium, registration deadlines, absentee ballot procedures, and the full slate of candidates so residents can plan how and when they'll cast their ballots.
![]()
3. 10 Connecticut Towns Retirees Are Fleeing Due To Rising Hidden Costs (newsbreak.com) — Westport retirees are feeling squeezed as high home values, property taxes, and everyday expenses make it harder to stay in town on a fixed income. The piece highlights how coastal home maintenance and insurance add hidden costs, but also notes that Westport offers senior property tax relief programs. Residents are urged to contact Town Hall for up-to-date eligibility details before deciding whether to downsize or move.
![]()
4. Westport LVW debate is latest cancelled reportedly for Sarelli's non-participation (westportjournal.com) — A planned League of Women Voters debate in Westport for the 26th State Senate District has been canceled after Republican candidate Alma Sarelli declined to participate, leaving no opponent for Democrat Samantha Nestor to face. Similar forums in Wilton, Ridgefield, and Redding were also dropped, and Nestor says she's disappointed Westport and district residents are losing a chance to compare candidates side by side.
![]()
📸 Around Westport
Show off your photography skills and the sights around town! Click here to submit your Photo of the Day to Patch AM!
🗓 Upcoming Events in Westport
Add your event to our calendar and newsletter!
★ Featured events ★
- Whale of a Sale →
131 Lamplighter Ln, Fairfield
9:00 am - Pre-Demolition/Moving Sale →
112 Roseville Rd, Westport
9:00 am - The Pumpkin Patch at St. John's Lutheran Stamford →
884 Newfield Ave, Stamford
10:00 am - Ian McKeever: Going Forth, Painted Panels & Other Works →
Heather Gaudio Fine Art, 382 Greenwich Ave, Greenwich
4:00 pm - Oyster Social →
Copps Island Oysters by Norm Bloom & Son, LLC, 7 Edgewater Pl, Norwalk
5:00 pm - "October Dance" - Dancing, Gathering, Having Fun! →
Ballroom Elegance Dance Studio, 877 Post Rd E, Westport
6:00 pm - Darien Cars & Coffee →
25 Old Kings Hwy N, Darien
7:00 am - When writing about Science is no longer just about reporting discoveries →
Wilton Quaker Meeting, 317 New Canaan Rd, Wilton
6:15 pm - Statewide Conversation Addressing Compassionate Health Care in the Age of AI →
1073 N Benson Rd, Fairfield
8:00 am - Complimentary Presentation - Strategies to Help You Make an Impact with Your Estate →
Online Event,
12:30 pm - Virtual: Free College Admissions & Financial Aid Workshop →
VIRTUAL,
7:30 pm - Seven Acres Montessori Virtual Prospective Parent Event →
Via Zoom, 34 Whipple Road, Wilton, CT,
10:00 am - FCDS Open House - Saturday, October 17 →
Fairfield Country Day School, 2970 Bronson Rd, Fairfield
10:00 am - Campaigning Class For Next Wave of Women in Politics →
Westport, Conn. venue available upon registration,
10:00 am - Campaigning Class For Next Wave of Women in Politics →
Westport, Conn. location provided upon registration,
10:00 am
Saturday October 10
Sunday October 11
Monday October 12
Wednesday October 14
Thursday October 15
Saturday October 17
Saturday October 24
Want to see your event featured? Click here!
Other local events
- Come See This One in Person! 🏡 →
1 Melon Patch Ln, Westport
9:00 am - Family Fun Day at MoCA/CT - October 10 →
MoCA\CT, 19 Newtown Turnpike, Westport
10:00 am - Murder Mystery Campfire →
Earthplace, 10 Woodside Ln, Westport
7:00 pm - Come See This One in Person! 🏡 →
1 Melon Patch Ln, Westport
1:00 pm - Indigenous Peoples' Day | Columbus Day School Recess →
MoCA\CT, 19 Newtown Turnpike, Westport
9:00 am - CLASP Presents - Radio Legends: Band Central Plays the Songs that Defined Generations →
StageOne at FTC, 70 Sanford St, Fairfield
6:30 pm - Restoring Hope 2026 →
Tashua Knolls Golf Club & Banquets, 40 Tashua Knolls Ln, Trumbull
6:30 am - Star 99.9 Goodwill Trick or Treat Day →
Sacred Heart University Discovery Science Center and Planetarium, 4450 Park Ave, Bridgeport
10:00 am - Woodside Bash →
10 Woodside Ln, Westport
6:00 pm - Westport's 2nd Town-Wide Tag Sale →
Westport, Westport
9:00 pm - The Enchanted Castle Presented by the Junior League of Eastern Fairfield County →
739 Old Post Rd, Fairfield
4:00 pm - The Space Between: A Clinician's Guide to Divorce, Emotional, Legal and Financial Readiness →
Westport Library Café, 20 Jesup Rd, Westport
9:00 am - The Enchanted Castle Presented by the Junior League of Eastern Fairfield County →
739 Old Post Rd, Fairfield
4:00 pm - SWING Dance Class - Beginner's Friendly! →
Ballroom Elegance Dance Studio, 877 Post Rd E, Westport
6:30 pm - The Enchanted Castle Presented by the Junior League of Eastern Fairfield County →
739 Old Post Rd, Fairfield
9:00 am
Saturday October 10
Sunday October 11
Monday October 12
Thursday October 15
Saturday October 17
Thursday October 22
Friday October 23
Saturday October 24
📣 Westport Shout Outs!
Want to say something great about someone in town? Click here to submit your Shout Out to Patch AM! It's free!
Have we missed something on our calendar? Add an event yourself! As always, before attending confirm event details to ensure accuracy.
Thank you 👏👏👏 to these businesses for making Westport PatchAM possible:
- Quartus Technology, Inc. — (866) 444-5596
- Gray Matters, LLC — 2032910880
- Michelle&Team — (203) 454-4663
- GxG Builders — (203) 994-6490
- Unquowa School — (203) 367-3151
- Green Giant Oil & Stone — (203) 254-0022
- Red Fashion School — (203) 690-4499
- C2C Home Edit — 2036047118
- Howard Hanna | Rand Realty — (617) 584-4317
- Needle | Cuda: Divorce and Family Law — (203) 557-9500
- Dogfather Grooming — 2039073626
- Putnam Insurance Agency, LLC — 2039671550
- Coldwell Banker — (203) 240-0624
- Sterling Marine Dock Builders — (203) 650-5601
- Ballroom Elegance Dance Studio — (203) 454-9400
- Modern Care Home Care — 4755506060
- California Closets — (203) 924-8444
Click here to show your appreciation! 💚
Want to see your business here? Click here to connect with local customers.
🪧 Patch Classifieds
- FCDS Open House - Saturday, October 17
Confidence. Curiosity. Character. It all starts with the right foundation. Discover how Fairfield Country Day School helps boys grow into capable,... (More info)
💬 Chatter
What your neighbors are talking about on social media
- There's no place like home — for training first responders. —Hartford HealthCare Read on Patch
- A safer ride starts with a helmet —Hartford HealthCare Read on Patch
- Obituary: Ulf T Mattsson —Markus Read on Patch
- I got a few boxes of kids books (including German books) I'd like to get out of my house.
Any ideas where would be a good place to donate? (Nextdoor Central Westport) - Can anyone recommend a good cleaning company or person?
I need to have my mother's very small apartment in Wilton deep cleaned this weekend. Please send recommendations! (Nextdoor Central Westport)
- Shake Shack posted a job opening for Restaurant Team Member in Westport. Apply here.
- Disabledperson, Inc posted a job opening for Investment Specialist - Southeast Region at NEOS Investments in Westport, Connecticut in Westport. Apply here. You can search for other jobs near Westport here.
Ok Westport! So now you're in the loop about what's happening today. Thanks for reading, and see you in your inbox next time! Oh -- and if you like what you're reading, invite a friend to Patch AM!
-- The Patch AM Team
P.S. The answer to today's riddle: "How do billboards talk?" — Sign language (Thank you Ellen S. for sending it in!)
Got a good riddle for PatchAM? Submit it here!
👉 Help make Patch AM better
- Help us grow by suggesting local news sources.
- Shape this newsletter with your feedback.
- List items for sale or services offered
We use a combination of real people and machines to tell you what's happening around town. Learn more about Patch AM.
Get more local news delivered straight to your inbox. Sign up for free Patch newsletters and alerts.