It was suddenly fall this week and cooler temperatures thankfully make mask wearing far more pleasant than in the sweltering days of July.  But, I am still sad to see the summer go. We have some important dates coming up, so let’s jump right in!



This past week, we had two important meetings related to our Comprehensive Plan.  Tuesday night, at our first Zoom Town Hall meeting ever, we were joined by our Town Planner, Valerie Monastra, for an update on our Comprehensive Plan.  Valerie, alongside Tiffany Zezula and Jessica Bacher from Pace University’s Land Use Law Center, walked us through a rough timeline of this project over the next twelve months, highlighting multiple opportunities for public engagement.  Our consultant specifically assigned to the Comprehensive Plan project, WXY Studios, has been working behind the scenes on evaluating existing conditions in the Town, and the team from Pace Land Use Law Center is crafting a community engagement strategy with help from our Comprehensive Plan Steering Committee.  Jessica from Pace also walked us through a draft Complete Streets policy their team prepared as part of another grant funded planning project Pace is working on with the Town.  If you were unable to join us on Tuesday night, please take some time to watch the YouTube recording of the meeting.  We are gearing up for our first public engagement session via Zoom in November, so stay tuned for more information very soon!



Then on Thursday, the Comprehensive Steering Committee met for our monthly meeting.  Valerie, Tiffany, and Jessica also joined us, and it was a very productive meeting as we all put our heads together to begin brainstorming on ways to best include all facets of our community in the planning process.  We will be looking for community groups, organizations, and more to lend a hand with outreach within the next few weeks.  This project truly hinges on participation and involvement from as many voices and perspectives as possible.  We want to hear from all of you as we collectively envision the Town of Ossining’s future.  If you have any ideas, or are part of a community organization with strong connections to residents and/or businesses here in Ossining, please feel free to reach out to me at This email address is being protected from spambots. You need JavaScript enabled to view it..  The more the merrier!



We are also gearing up for Car Free Day, which is just one week from today.  With wildfires in the west and hurricanes Sally, Terry, Vicky, and Paulette in the Atlantic, we know climate change has been an issue on a lot of people’s minds this week. On September 25th, 511NY Ride Share is hosting the “Go Car Free Day for Climate” Challenge in the Hudson Valley. Take the NYS Pledge to go car free, and have your emissions reductions count towards the overall total. Let’s see if we can beat last year’s mere 45 who took the pledge.  Many people are already working from home, so by taking the pledge, it is a great chance to be easily entered for some fun prizes. It just takes a minute. Use the hashtag #NYSCarFree to share photos and stories of how to go car free in the Town of Ossining or how you went car free. Ossining has bike lanes, sidewalks, and some lovely outdoor space. The goal is help us all realize how much time we spend behind the wheel, most of the time burning fossil fuels while doing so, and how much our individual actions contribute to climate change.  Green Ossining would also love to hear how you are celebrating Car Free Day this year.  In addition to taking the pledge, follow up by responding to this quick survey from Green Ossining.  This will help the Ossining community plan even better next year, when we can hopefully gather together to celebrate once again!


Ibanez covid announce2 e1598021738406


There are only 12 more days to respond to the US Census! That is less than two weeks to help our community get the funding and representation we deserve. Ossining lost $2500 per resident per year since 2010 because of our response rate. Have you responded yet? For the next 12 days, I ask that you help us get the word out. It only takes 10 minutes to complete and you can still fill it out online or on the phone (844-330-2020 in English and 844-468-2020 in Spanish). The Town of Ossining Facebook page is going to be sharing a lot of Census related reminders in the next few days. Help us get the word out about this end-of-month deadline.



Census Thermometer 9.15.2020 eng


Census Thermometer 9.15.2020 esp


The first half of School Tax bills for both the Ossining and Briarcliff School Taxes are due by September 30, too. The bills are available for online payment on the Town’s Website.  Here are the ways you can pay your taxes:

  • Online: We are strongly encouraging taxpayers to pay online (an e-check is $1.50 through our system). For help with the online payment system, the Tax Office created a downloadable easy online guide.
  • Tax Office dedicated Mail Slot at Ossining Post Office: You can pay by mail or drop off your envelope (with a stamp!) at the dedicated Tax Office mail slot at the Ossining Post Office. (If using the dedicated mail slot, the USPS will postmark mail for the day it is placed in the slot up to 5pm that day, otherwise it will be postmarked the next day).
  • Mail: Drop your payment in any mail box or at any post office. Only bills postmarked by September 30 will be considered timely.
  • In-person: If you would like to pay in person, you are welcome to come to our building at 16 Croton Avenue in Ossining during our public office hours (9am to 2:30pm, Monday through Friday). Please bring exact change if you will be paying in person with cash. The Tax Receiver’s Office is ready to assist you if you have any questions about your bill.



Be wary of the online bill pay option through your bank! Although your account is debited immediately, it often takes at least a week for checks to arrive in our office – yes via snail mail. These envelopes from banks are not postmarked, so we can only mark your bill as paid once the check has been received and processed by our office. If you want to complete your transaction online, going through the Town’s Xpress-Pay is truly the best and fastest way. The Tax Receiver’s Office is ready to assist you if you have any questions about your bill. You can call them at (914) 762-8790 or send an e-mail to This email address is being protected from spambots. You need JavaScript enabled to view it.. Tax Receiver Holly Perlowitz and her staff are very helpful if you have any questions.





September means school is back in session, with college campuses around the country navigating the COVID-19 landscape. You may have noticed an increase in County-wide numbers this week. Many of these cases are connected to students studying in other states, whose home address is connected to their health insurance. When these young people test positive, their “home address” can be charted on the map here locally, rather than their campus address. While this issue has been raised with the County, it is not so easy to untangle with insurance companies involved. This by no means explains away all the active cases in Westchester, but rest assured we are carefully monitoring the daily numbers.



Back to school this year brings unprecedented challenges for many families.  Here are some resources available to families as we adjust to our new normal:



Ossining Recreation is offering free Wi-Fi access for students who need an internet connection to complete their virtual studies. Students are required to bring their own devices, headphones and masks. Wi-Fi access will be available for two daily sessions Monday through Friday, until December 22. Session 1 will last from 9AM to 11AM each day, Session 2 will last from 11:30AM to 1:30PM. Students should enter through the Community Center's rear entrance and students under the age of 14 require adult supervision. Register here to reserve a spot.





Ossining Parks & Recreation is also offering an After School Program for the 2020-2021 School Year for children in grades K-6. The program will include homework assistance, reading time, art projects, games, etc. You can choose from a one-, two-, four-, or five-days-a-week schedule for up to three hours of supervised care through the Community Pass Program.


after school



Starting this week, the Ossining School District is offering free meals Mondays and Wednesdays from 5 to 7pm. This program is expected to run until the end of 2020, though it is at the discretion of the Federal government. The meals are for 18 year olds and younger.


ENG schools


ESP schools



You can celebrate some of Ossining’s amazing teachers by checking out the NYS Art Teachers Association Annual Member Show, entitled “Art in the Time of COVID” featuring Ossining Schools’ art teachers Terrie Bentley, Catherine Ibanez, and Ron Whitehead.  This Saturday, September 19 will be the virtual opening reception and you can check out the artwork either virtually or in-person starting now and running through October 31.  Ms. Ibanez was also recently recognized as the New York State Art Teachers Association Region 7 Elementary School Art Teacher of the Year for 2019-2020!  Congratulations Ms. Ibanez, and definitely go check out her amazing artwork now!  The image below is one of her colorful portraits she creates of family, friends, and for this art show, some of the heroes of the COVID-19 pandemic like the healthcare worker pictured here. 


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Another sign of autumn besides back to school? The Town is hiring two laborers to help during leaf removal season. You can find the application and details about the job on the Town of Ossining website. Please return the completed application by Friday, September 25 to Victoria Cafarelli by email at This email address is being protected from spambots. You need JavaScript enabled to view it. or in person at the Municipal Building in Ossining (at 16 Croton Avenue).  Visitors are still limited to the first floor, but our Clerk’s office has lots of applications on hand and is ready to help!


Hiring Seasonal Laborer



As I am sure no one has forgotten, Election Day is around the corner. If you are eligible to vote but are not registered, be sure to get your name on the list. The last day to register to vote for the November general election is October 9, in person or by postmark. Register now! It is simple and easy, and you can even register online. Our Town Clerk’s office at 16 Croton Ave in Ossining also has plenty of voter registration forms and absentee ballot applications available to the public. Stop by the Clerk’s office in person Monday through Friday during our public office hours (9am to 2:30pm).



As you may know, polling places are often school buildings, fire houses, and other public buildings. Due to the threat of COVID-19, some of our regular polling places for Election Day in-person voting may be different. Prior to November 3rd, you will receive a postcard in the mail from the Board of Elections which will let you know exactly where to go. If you bring it in with you to the polling place, they can scan the QR code for you to speed up your in person voting experience.



If you want to vote by absentee ballot, you may have already received an absentee ballot application. Following a change made by Governor Cuomo, the “unable to appear at the polls due to illness or disability” option has been expanded for anyone looking to reduce their risk of exposure. If you choose to fill out the application, get it in the mail right away to give the Westchester Board of Elections time to review your request and mail you the actual ballot. If you did not receive an absentee ballot application you can apply for a ballot on the Westchester County Board of Elections website or through the New York State portal. The deadline for requesting an absentee ballot is October 27 by mail, or up until November 2 if applying in person. You can also submit your application if you request it from the Westchester Board of Elections via e-mail to This email address is being protected from spambots. You need JavaScript enabled to view it..



Early voting, starts on October 24 and here’s something not many people know: this election, you can vote at any of the seventeen early voting locations throughout Westchester. For a complete list of locations and hours, visit the Board of Elections website. Find the one that is most convenient for you. The most local location for Town of Ossining residents will be the Ossining Community Center at 95 Broadway.



2020 Voting



The Westchester County Board of Elections is also hiring!  Come on board to help reduce wait times at polling places. Many senior citizens who work on Election Day have declined this year due to Coronavirus risks. You can participate in the democratic process by coming on board for $350 a day (remember there are early voting days and training days available). You must be a registered voter and 18 or over to be hired. Visit the Board of Elections website and scroll to the “Poll Worker Application Form.”


Election Workers Needed



People who are unemployed, self-employed, or who cannot get insurance through work often struggle to get access to health coverage. The Westchester County Department of Health’s Insurance Access Program provides residents with free or low cost insurance through New York State’s Health Marketplace, which was created by the Affordable Care Act. You may be eligible for free or low-cost coverage through Medicaid, the Essential Plan, or Child Health Plus, or you may qualify for a Qualified Health Plan with tax credits. You can learn more about the plans available at 914-995-6350 or This email address is being protected from spambots. You need JavaScript enabled to view it..


westchester doh


westchester doh esp


Sing Sing Kill Brewery and Crossover Yoga Project are partnering again for a Poses2Pints FUNraiser this Sunday, September 20. You can zoom into the event, which will also be streaming live. Tickets are $10 and come with a $5 coupon to the brewery. Learn more about the event on the Sing Sing Kill Facebook event.


Pints to Poses



Also on Sunday, September 20th Teatown Lake Reservation is hosting Magnificent Animals, a chance to meet some of the amazing creatures they care for. Bring a blanket or a chair and join the team on the lawn from 11am to noon for a program featuring Teatown’s animal ambassadors. Teatown is a 1000-acre nature preserve and education center, and their animal ambassadors are generally abandoned or disabled animals who cannot survive on their own in the wild. You can learn more about the adorable ambassadors on their very own page on the Teatown Website.





On September 22, the Sing Sing Prison Museum will present a webinar titled Justice Talks; COVID-19 and Incarceration. The webinar will discuss what is occurring on the federal and local level, the realities and history of disease inside prisons, and what the experience of being incarcerated under these circumstances means. The museum has assembled a panel of experts on criminal justice, epidemiology, and advocacy who will explore what is happening and what more can be done in a moderated conversation. The event will be streamed live on Facebook, you can also register here.


Justice Talks



The Briarcliff Public Library is hosting a virtual workshop about voting on Wednesday, September 23rd starting at 7pm. Registration is required to receive the Zoom invitation for the workshop. To register, please reach out to Shelley Glick at This email address is being protected from spambots. You need JavaScript enabled to view it. or call the Briarcliff Library at 914-941-7072.



Briarcliff Library LOWV voting info



Starting September 24, WestCOP is offering new volunteer training for Rape Crisis Helpline Counselors. As you may know, their last training was moved to a virtual setting and this newest one will remain virtual as well. Bilingual volunteers are encouraged to join the team. The training will take place every Thursday from September 24th through November 24th, from 6PM to 9PM. Participants will become NYS Department of Health certified Rape Crisis Counselors. For more information and zoom information, please contact Brenda Luna at This email address is being protected from spambots. You need JavaScript enabled to view it.  or Rosani Jimenez at This email address is being protected from spambots. You need JavaScript enabled to view it..








Also on Saturday, September 26 Green Ossining is hosting an event to clear invasive species from Crawbuckie Nature Preserve. Volunteers must wear a mask and gloves, long pants/long shirt preferred if sensitive to poison ivy, and bring loppers or saws. Please remember that hydration is crucial during high heat and humidity so bring water (and a snack). Pre-registration was required by Friday, August 7th through the Community Pass Program. Please call the Recreation Center if you would still like to register but missed the deadline, at 941-3189.




With spooky evenings fast approaching, tickets are now available for Hulda’s Night in Rockefeller State Park Preserve. Hulda was a woman who fought and died in the Revolutionary War. Legends about the woman as a healer and her age make the “Witch’s Spring Trail” a fun October event. Visitors are guided by torch light through the dark woods, across wooden bridges, and through the forest to the place historians believe Hulda’s actual home may have stood. Meet “Mother Hulda” and Storyteller Mike at Spook Rock to hear other legends that have their origins within the Rockefeller State Park Preserve. Register on the Park’s Eventbrite page.


huldas legend



The start of September also means the start of a slower season for restaurants. Generally, April through August (when the weather is nice) more people are willing to order food. This is obviously a little different in 2020, but it is still important for us to keep in mind. Our restaurants are a vital part of the local economy and we ask that you continue to support them whenever you can. We know many people are concerned about this week’s CDC report that seemingly connects dining out with an increased risk of contracting COVID-19, but there are other options available. If you are uncomfortable with indoor dining or sitting near others, you can order take out and eat in one of our beautiful parks. Too chilly for your tastes? Who can beat yummy take out in the comfort of your own home? Help promote your favorite place online, recommend your favorite dishes, and help support our beloved eateries.


fave restaurant 


Finally, I want to end by congratulating the hard working volunteers of Croton Mask Makers.  This week, the Croton Mask Makers made their thirty thousandth mask. What an amazing achievement. Despite the name, members of this group are from across the county, Ossining included, and have worked (virtually) together to make masks since March.  Many of you have donated material or graduation gowns to this group along the way. The group is still going strong, sending masks to schools, hospitals, and individuals around the country. Please join me in congratulating them.


croton mask makers



L'Shana Tovah to those who celebrate Rosh Hashanah and wishing everyone a much sweeter New Year!





If your business, non-profit, or community group has an event that you would like to submit to be a part of the Supervisor's Update, please e-mail a flyer and brief description to This email address is being protected from spambots. You need JavaScript enabled to view it.. We are happy to pass along events that provide a benefit to the community and support our local economy. Thank you for helping us to highlight all the best Ossining has to offer!