Ossining Annual Celebrations and Festivals 2019 | InOssining.com

Ossining Annual Celebrations and Festivals

There are so many events held every year in our town! You’ve probably heard about the Ossining Village Fair and the Earth Day Festival, but there are many other great celebrations and festivals that the town and local organizations hold each year that you should know about (and go to!).

Here is a list of our yearly events organized by date. Each celebration or event will have an events page in our Ossining Events Calendar, so head over there for specific dates and times and more info as it becomes available.

March or April: Eggstravaganza

Easter Ossining celebration

Play Games, win eggs, bring your camera to take a picture with the bunny and enjoy entertainment with Annie and Safari Bob. 
2 Sessions 10:00 am & 11:00 am
This free program is by registration only, for ages 2-9.

– Host: Village of Ossining Recreation and Parks Department
Where: Joseph G. Caputo Community Center (Recreation Center
When: Saturday, April 13th 2019

April: Earth Day Celebration

Earth Day Festival in Ossining NY


Westchester County’s LARGEST community-run Earth Day Festival is hosted and organized by Green Ossining with the assistance of the Town and Village of Ossining.

Join the Greater Ossining community in our annual celebration of Earth Day. Bring family and friends. Learn how to live a more sustainable life, visit artisan vendors, and enjoy food and live music on the banks of the Hudson River.

Featured events of the day include:  Arts & artisan vendors, eco-demonstrations & hands-on activities,  focused kid’s activity zone, environmental advocacy, zero-waste in action on the festival grounds, delicious local food including vegetarian and vegan fare, craft beer, textile recycling & e-waste drop off, live music with local musicians, local “green” services/product vendors available for sharing green practices and products.
Your can see pictures of the 2019 Earth Day Celebration Here

Host: Green Ossining
Where: Louis Engel Waterfront Park
When: Saturday, April 27th 2019

May: CLASSIC Car show

Join the Christopher Columbus Lodge #692 for their classic car show featuring cars, trucks and motorcycles. Food, soda and coffee will be available, as well as free popcorn and fun music.

Host: Christopher Columbus Lodge #692
Where: Ossining Train Station
When: There was no car show on 2019

June: Ossining Village Fair

Ossining Village Fair

The Greater Ossining Chamber of Commerce hosts Westchester’s largest street fair in historic downtown Ossining on Main & Spring streets. There are plenty of food options, crafts, local organizations’ booths, entertainment stages, children’s rides and games, and much more.

In years past, this event has hosted over 18,000 attendees.

– Host: The Greater Ossining Chamber of Commerce
Where: Historic Downtown Ossining
When:  June 8th 2019

June: Portugal day Festival

Enjoy the flavors of Portugal with food, vendors, folklore groups and music. This event has been held for over 20 years.

– Host: Ossining Portuguese Club
Where: Historic Downtown Ossining, Main Street
When:  June 15th 2019

June: Saint Ann’s Festival

Celebrate the end of the school year at this annual event held at the Saint Ann’s school grounds, located on Eastern Ave., up the hill from Route 9. There are lots of rides for the kids, a casino and arcade, and food from different parts of the world!

– Host: St. Ann’s school and church volunteers
Where: Saint Ann’s school
When:  June 25th-30th 2019

July: fireworks celebration

Fireworks in westchester 
The Village of Ossining Recreation and Parks Department puts on a great fireworks show for the town. The event starts with a concert at 7:00pm and the fireworks begin at approximately 9:00pm.

It’s a great way to kick off the holiday weekend!

Host: Village of Ossining Recreation and Parks Department
Where: Louis Engel Waterfront Park
When: Wednesday July 3rd 2019 (see event here)

July & August: Summer Concert Series

Ossining Waterfront Concert Series 2019


On Fridays in July and August, local bands take the stage at Louis Engel Waterfront Park for a 7:00pm show. The concert series features a variety of local performers and the musical acts cover a wide range of genres from classic rock, pop, latin and jazz, to urban folk, funk, and R&B.

Concertgoers are encouraged to bring blankets or foldable chairs for seating. Picnics are welcome and food is also available for purchase. All concerts take place at Louis Engel Waterfront Park. In the event of rain, the concerts will be held at the Ossining Public Library’s Budarz Theater.

Host: Village of Ossining Recreation and Parks Department
Where: Louis Engel Waterfront Park
When:  Every Friday starting July 5th, until August 30th (with the exception of August 2nd) See More Here

August: Saint Augustine’s Italian Festival

Saint Agustines Festival 
St. Augustine Church celebrates a 6-day (Tuesday to Sunday) Italian Festival with delicious food, lots of rides, fireworks, casino, games, and a fireworks display (on Wednesday).

Discounted advanced purchase pricing is normally available for vouchers for unlimited ride wristbands for Tuesday, Thursday and Sunday evenings.  Unlimited ride wristbands may still be purchased each night at regular pricing from the ticket booth at the festival.

  If you do not want an unlimited ride wristband, you can instead purchase a fixed number of tickets which can be exchanged for access to rides.

Host: St. Augustine Church
Where: 381 North Highland Avenue or Route 9, Ossining
When:  July 23-28th 2019

August:  Annual Ossining Fire Dept Parade


The Annual Ossining Fire Department Parade takes place at the beginning of August. The parade starts at 7:00pm (for those participating, line up is at 6:00pm). The Parade start is on Croton Ave at Campwoods Rd and will head west on Croton Ave to Highland Ave and proceed south on South Highland Ave to Main St, then West on Main St continuing on to Secor Rd and ending at the Louis Engel Park at the waterfront.  

– Host: Ossining Fire Dept.
– Where: From Croton Ave to Louis Engel Waterfront Park
 When:  August 2nd 2019

October: Fall Family Fun Day


Celebrate the arrival of Fall with a day of fun family activities including hayrides, face painting, pumpkin painting, a pie eating contest, live music and crafts!

Host: Village of Ossining Recreation and Parks Department
Where: Market Square, Intersection of Main and Spring Street
When:  October 5th 2019

October: Halloween Spooktacular

Families are invited to join Ossining’s first responders downtown on Halloween night for Trunk-or-Treat! The celebration starts with a costume parade that ends on Main Street, where families can enjoy bouncy castles, games, music and lots of candy.

Police cars, fire trucks and ambulances are decorated for everyone to enjoy and feel the spirit of Halloween, and kids can go trunk to trunk to do their trick or treating in a safe and fun environment.

Host: Village of Ossining Recreation and Parks Department
Where: Main Street
When:  October 31st 2019

October: Forest O’Fears

Halloween in Ossining

Forest O´Fears is for the whole family. Brave kids and adults can head over to the scary haunted house with two floors, a butcher that will “meat” attendants, a confusion room, a morgue, and lots of scary characters.

For the little ones there is a Halloween Village with live music, food, games like Mummy Flush, Chip’s Pumpkin Fling and Franken-toss, a fire show, the “Unhaunted Hayride”, and the Homespun Merry-Go-Round for the littlest Halloween enthusiasts in your family.

Host: Village of Ossining Recreation and Parks Department (and volunteers)
Where: Cedar Lane Park
When:  October 18-19 & 25-26, 2019

December: Ossining Tree Lighting

Ossining Christmas Tree Lighting

Join the local community, Town and Village of Ossining and the Greater Ossining Chamber of Commerce as Ossining officially kicks-off off the Christmas & Holiday season! Everyone in the community is invited for the annual Christmas Tree Lighting Ceremony, to sing carols, enjoy live performances, hot chocolate, cider, cookies & of course a visit from Santa, who arrives on a fire truck.

Host: Village of Ossining Recreation and Parks Department and the Ossining Chamber of Commerce
Where: Market Square
When:  The date for 2019 hasn’t been announced

December: Breakfast with Santa

Ossining kids can have their own Santa encounter at the Recreational Center. Kids will get a small gift and the opportunity to give their wish list to the Jolly Elf from the North Pole. Entertainment will be on hand to delight the young ones. There are two sittings for breakfast (10:00 and 11:00am) and every participant must register in advance at the Recreation Office.

Host: Village of Ossining Recreation and Parks Department
Where: The Joseph G. Caputo Community Center
When:  The date for 2019 hasn’t been announced

These are a number of the highlights that await Ossining residents this year and every year!

  • Barbara says:

    July 3 is a Wednesday – for Ossining fireworks. Your site says Tuesday

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