5 Things to Do in Ossining This Fall | InOssining.com

5 Things to Do in Ossining This Fall

It’s hard to believe that fall is just around the corner; September 22 to be exact! Fall brings lots of (mostly outdoor) activities to Ossining residents. For the next couple of months, there are enough local festivals, celebrations, fundraisers, places to go and things to do to keep you and your family occupied and enjoying the outdoors before the chilly winter weather arrives. Below are a few of our favorite things to do in Ossining in the fall!

1. Go to a fall festival

Fall Festivals are happening all around Ossining. The first one to take place is Fable’s Fall Farm Festival on Sunday, September 23rd, where guests can purchase farm fresh goodies, shop at local artisan vendors, tour Fable’s greenhouse and feed the chickens, all while enjoying live music.

The next weekend, on Saturday, September 29th, the Maryknoll Sisters have their yearly Fall Festival, a great day of fun for the whole family, with games, activities, entertainment, food and vendors. All proceeds from the Festival will benefit the Sisters worldwide mission work to help those in need.

On October 13th, the Ossining Recreation and Parks Department will hold their annual Fall Family Day to 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!

And if you are ready to start your holiday shopping, don’t miss the Fall Artisan Market presented by the artists, makers and designers of the Northeast Etsy Artists Collective. Discover and shop for beautiful and unique handmade gifts for everyone on your list! From pottery to accessories to skincare, you’re sure to find something special. Vendors will donate 15% of sales proceeds from the event to Bethany Arts Community.

Things to do In Ossining

2. See the colors change

One of the great things about living in the suburbs is that we have plenty of hiking trails and parks to see the seasons change. The Town of Ossining has over 130 acres of parkland, 19 parks and is home to Teatown, a nonprofit nature preserve and environmental education center with 15 miles of hiking trails.

Our favorite parks to see the fall colors are Crawbuckie Nature Preserve, Cedar Lane Park, and Sally Swope Sitting Park. Our favorite Teatown hike is the 1.5-mile Lakeside Trail, mostly because I have little ones and they can do this hike all on their own, while discovering new sounds and animals that live in and around Teatown Lake. You can see all the trails on the trail map which you can access from this page on the Teatown website.

Crawbuckie Nature Preserve also has river views, particularly when the leaves start to fall

Crawbuckie Nature Preserve also has river views, particularly when the leaves start to fall

3. Participate in the town-wide tag sale

The Green Ossining semi-annual Community-Wide Tag Sale will take place on October 4th. It’s a fun event to make some money, help the environment, maybe pick up a few things you need, and meet your neighbors. Register before September 29th if you have want to participate and keep your no longer needed items out of the waste stream. On October 4th, the map of participating households will be available on the GreenOssining website.

Green Ossining Tag Sale

4. Have a spooktacular Halloween

The Ossining Police Department along with the Ossining Recreation & Parks Department invite everyone to celebrate Halloween at the 3rd Annual “Halloween Spooktacular” on Main Street. The event will feature a costume parade, “Trunk or Treat”, DJ/music, inflatables and of course CANDY! It will be held on Halloween, and last year’s start time was 5:30pm.

On October 26th and 27th you can scream your heart out at the super scary 6th Annual Forest O’Fears Haunted Hayride at Cedar Lane Park. At last years event, Halloween enthusiasts enjoyed a hayride through the Forest O’Fears, live entertainment, a hay bale maze, carnival games, a child-friendly hayride and a fire manipulation show by Flaming Barrel of Monkeys Entertainment.
The Forest O’Fears event is produced by Ossining residents along with a cast and crew of almost 100 youth and adult volunteers and Town of Ossining Parks staff.

As soon as we have all of the details of this year’s events, we’ll update the above info.

Ossining Forest O Fears

5. Walk the Sing Sing Kill Greenway

The Sing Sing Kill Greenway is a concrete walkway opened in 2016 that runs down the Sing Sing Kill gorge. Even though you are practically in the middle of Ossining’s Old Village, you will be able to see red, yellow, green, brown and orange leaves. Pair it with a pumpkin latte from First Village Coffee, and you can enjoy a perfect fall afternoon right here IN Ossining!


Bonus Activities:

Ossining Non-Profit Organizations Fundraising:


Please feel free to share other events or activities happening this fall in the Town of Ossining.
We are happy to promote your event and share it with other Ossining residents looking to enjoy this season.
Just add a comment below or fill out our Event Form and we will add your event to our Calendar.

Scroll to Top