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 (April 20nd 2024), 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.
Bookmark this article and come back to see updated dates and information.
March: Eggstravaganza
Play Games, win eggs, bring your camera to take a picture with the bunny and enjoy entertainment with Annie and Safari Bob.
– Host: Village of Ossining Recreation and Parks Department
– Where: Joseph G. Caputo Community Center (Recreation Center)
– When: On 2024 this event was replaced by the Ossining Bunny Run on March 16th 2024.
April: WoodFest
Discover the magic of Bethany Arts Community’s third annual WoodFest! Come experience the joy and wonder of the natural world, brought to life through the skillful hands of artisans. WoodFest has something for everyone, from handcrafted creations, to wood sculpture demonstrations, to wood-crafting activities for all. Enjoy a day of arbor and wood celebration with live music, art, activities, and games for the whole family!
– Host: Bethany Arts Community
– Where: Bethany Arts Community, 40 Somerstown Rd. Ossining
– When: Saturday April 27th 2024 / 11AM-4PM
– More info: WoodFest
April: Earth Day Celebration Festival
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.
– Host: Green Ossining
– Where: Louis Engel Waterfront Park
– When: Saturday April 20th 2024
– Read more about this Event HERE
– See Pictures from Earth Day 2019 HERE
– More info from Green Ossining: HERE
May: Memorial Day Parade
The Ossining Memorial Day Parade is a cherished annual event that pays tribute to the brave men and women who have served and sacrificed for their country. Spectators line the streets adorned with American flags as marching bands, veterans’ organizations, and local groups like the boys and girls scouts of America, proudly march in honor of the nation’s fallen heroes.
– Host: The Central Committee of Organized War Veterans of the Town of Ossining.
– Where: The parade starts at 9:30 a.m. at the intersection of Croton and Calam Avenue and ends at Nelson Park.
-When: On Memorial Day, Monday May 27th 2024
– Best place to see the parade: Main Street
– More info and photos HERE
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.
You can see pictures of Portugal Day in Ossining HERE
– Host: Ossining Portuguese Club
– Where: Historic Downtown Ossining, Main Street
– When: June 15th 2024, 12-11PM
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 18-23 2024, 6PM-11PM
– More info: St Ann’s Festival
July: Fireworks Celebration
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: July 3rd starting at 5 PM with two live bands before the fireworks
– More info: Ossining Riverjam Summer Concerts
July & August: Summer Concert Series, Ossining Riverjam
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: Friday Nights July – September. The specific dates for 2024 haven’t been announced
– More info: Ossining Waterfront Concerts
-Event website: Ossiningriverjam.com
July & August: Family Entertainment Series
Beginning on Tuesday, July 9th family friendly shows will take place every Tuesday at 7:00PM. The family entertainment series, features a variety of fun performers and will run through August 13th 2024.
– Host: Village of Ossining Recreation and Parks Department
– Where: Different Ossining Parks
– When: Tuesday Nights July – August 2024
- July 9th David Levitan at Market Square
- July 16th David Darwin One man Sideshow at Henry Gourdine
- July 23th Bubble Bus and Larger than Life at Nelson Park
- July 30th Squeaky Clean Band at Market Square
- August 6th (rain date August 20th) Parrot Beach at Louis Engel Waterfront Park
- August 13th Music Bingo at Market Square
– More info: Post with details on performers coming soon.
July & August: Summer Acoustic Series
Beginning on Wednesday, July 10th acoustic shows will take place everyWednesday at 7:00PM. The Summer Acoustic Music Series, features a variety of local musicians and will run through August 14th 2024.
– Host: Village of Ossining Recreation and Parks Department
– Where: at Market Square
– When: Tuesday Nights July – August 2024
- July 10th Jamie Cairney, Classic Rock, country and Folk
- July 17th Sundad, World Fusion, New Age
- July 24th Nat Longordo, Classic Rock from the 70s to today
- July 31st Novablue, Latin, Jazz and Brazilian Standards
- August 7th The Jacobs, Pop/Rock
- August 14th Midnight Maizey, Folk, Country, Indie, Rock
– More info: Post with details on performers coming soon.
July & August: Jazz at Henry Gourdine Park
Located on the shores of the Hudson River in Ossining, NY, this free concert series takes place on alternate Monday evenings in July and August. Bands perform on the open-air plaza, next to the large arch sculpture, adjacent to the ferry which transports folks to Haverstraw, NY on the western side of the Hudson.
– Host: Jazz Forum Arts
– Where: Henry Gourdine Park
– When: July 15th and 29th and August 12th and 26th 2024
-Event website: Jazz Forum Arts
– Event pictures and more info: Ossining Waterfront Jazz Concerts
August: Saint Augustine's Italian 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 24-27 2024
– More info: St Augustine’s Festival
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 Department.
– Where: From Croton Ave to Louis Engel Waterfront Park
– When: August 2nd 2024
September: Ossining Day
(Formerly Ossining Village Fair)
The Greater Ossining Chamber of Commerce is re imagining the beloved Ossining Village Fair to better serve Ossining Business and Residents. Stay tuned for more information. We are excited!
– Host: The Greater Ossining Chamber of Commerce
– Where: Historic Downtown Ossining
– When: September 21st 2024
September: Ossining Hispanic Festival
Celebrate The Hispanic Heritage month with dances, performances, live music, arts and crafts and food representing different Hispanic and Latin cultures.
– Host: Ossining Padres Hispanos
– Where: Market Square
– When: Sunday September 8th 2024
October: Artoberfest
Featuring visual artists, live musicians, food, live and interactive demonstrations, the festival will be a great experience for all ages! ARToberfest will illuminate arts spanning a variety of styles and mediums and celebrate the unique culture of the Hudson Valley region.
– Host: Bethany Arts Community
– Where: Bethany Arts Community
– When: October 5th 2024
– See pictures HERE
October: Spooktacular Fest
Come out in costume for the Spooktacular Fall Fest, featuring live bands, games, face painting, a trunk-or-treat, bouncy houses, and a pet parade, plus a beer garden and live music for adults.
– Host: Ossining Chamber of Commerce
– Where: Ryder Park
– When: There was no Spooktacular Fest in 2024
October: Pumpkin Patch and Hayride
Are you looking to get into the Halloween spirit? Well, look no further than the Pumpkin Patch at Nelson Park, hosted by Ossining Police Department and the Recreation & Parks Department.
Children ages 12 and under are invited to the Pumpkin Patch between 4:00 and 9:00pm. After the ghosts and goblins choose their perfect pumpkin, they can enjoy a donut & cider as well as a hayride!
Costumes are optional, but reservations are required! Please register each child who will be attending.
– Host:Ossining Police Department and the Recreation & Parks
– Where: Nelson Park
– When: October 25th 2024
October: Halloween On Main Street
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 2024
December: Ossining 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: December 6th 2024
– More info: Ossining Tree Lighting 2024
December: Ossining Menorah Lighting
Families, friends, and neighbors gather around the menorah, their faces illuminated by its warm glow as they sang traditional songs and shared in the festive spirit of Hanukkah. The event served as a reminder of the diversity and strength of the Ossining community, fostering a sense of togetherness and solidarity.
– Host: Chabad Lubavitch of Briarcliff Manor and Ossining.
– Where: Market Square
– When: Thursday December 25th at 3PM
– See pictures of the Menorah Lighting HERE
December: Candy Cane Run
Santa goes around town spreading Holiday Cheer (and candy canes). If your house isn’t on the route, come down to one of the parks at the times listed below with a “STOP” next to them. Santa wishes he could visit every street and house in Ossining but our vehicles lack the magic of his sleigh, so he is making due with what he has and doing his best to bring joy to as many residents as possible.
– Host: Ossining Police Department, Ossining Volunteer Ambulance Corps, and the Ossining Fire Department.
– Where: All around town
– When: The date for 2024 hasn’t been announced.
– See last years Route HERE
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 2024 hasn’t been announced.
– Watch a -Instagram- Reel for this event
These are a number of the highlights that await Ossining residents this year and every year!
July 3 is a Wednesday – for Ossining fireworks. Your site says Tuesday
Hi Barbara
Thank you so much for pointing that out.
I’ll fix it!