A Mom’s Guide To Westchester County Events :: September 2018


Summer is ending…sigh…but that means a lot of fall fun. September weekends are a time to have fun with the family by apple picking, finding one of the endless festivals in the county, or spending time enjoying the changing season. Luckily, Westchester is jam packed with events for everyone to enjoy this September.  

September 1-3

  • Philipsburg Manor, Sleepy Hollow :: CORNucopia is a three day event that is sure to be anything but corny. Bring the family and challenge yourself to a corn maze, enjoy entertainment, and have fun. Ticket prices are up to $16. 

September 7-9

  • Downtown Yorktown :: Various times over the weekend, The Yorktown Grange Fair is open to the public. Explore American values and traditions with this old time fair. Includes a tractor parade on Saturday, September 8th at noon. Midway games, hayrides, food and fun. This is a great way to welcome fall with the family.
  • Holy Trinity Church, New Rochelle :: Celebrate the Greek Heritage Festival with delicious Greek food, listen to music, enjoy rides and vendors. This fun filled weekend is sure to please the whole family.
  • Germania Festival Grounds, Poughkeepsie :: Join the fun with Oktoberfest. Enjoy a little bit of Germany right here in Westchester. Enjoy German food, music, citizenship and fun. Adult tickets are $6 with free parking. Rain or shine.

September 7

  • Memorial Park, Mamaroneck :: Starting at dusk, the last movie in the park series is sure to be a hit with a showing of Toy Story. This is a free family event. Rain date September 14.

September 8

  • Riis Park, Harrison :: From 11:00 -3:00 p.m. visit the Play2Learn Festival. This free event for children and families will give kids of all ages a great chance to play and explore with over 40 different activities. Food and entertainment will also be on hand.
  • Draper Park, Hastings on Hudson :: The River Spirit Music and Arts Festival will be packed with activities and vendors for the first River Spirit Music and Arts Festival. Musicians will be performing sets from 11 a.m. – 9:30 p.m. More info at riverspiritmusic.com

September 9

  • Main Street, New Rochelle :: From 11:00 – 5:00 p.m. the 6th Annual Street Fair will run. This fun filled family event includes artists, crafts, entertainment and food. This fair has become one of the largest downtown events in lower Westchester and is fun for the whole family.
  • Harbor Island, Mamaroneck :: Starting at 11:00 am is the 45th Annual Kiwanis Car Show. Come to the harbor to see cars of all types and kinds. This is a charity event with a $10 donation for all visitors ages 10 and up.

September 14-16

  • Mount Kisco Chamber of Commerce :: From 10:00 am – 6:00 pm. celebrate Mount Kisco’s largest block party. It is so big it lasts for three days! You will surely find something for everyone. Sidewalk sales, carnivals, even a beer garden! End the weekend with the Kisco 5k Sunday at 8:30 a.m.

September 15

  • Harbor Island, Mamaroneck :: Starting at 7:30 p.m., Movies Under the Stars presents a showing of the live action, Beauty and the Beast. Bring blankets and lawn chairs for a movie on the sand.
  • Main Street Downtown, Yonkers :: From 12:00 – 6:00 p.m. is the Yonkers Riverfest. This free event is fun for the whole family and features music, food and fun throughout downtown Yonkers.
  • Various Downtown Locations, White Plains :: From 11:00 a.m – 8:00 p.m. is JazzFest 2018. Start the day with the farmer’s market and stay for a fun variety of family friendly Jazz concerts and activities.
  • Read Sanctuary, Rye ::  From 10:00 a.m. – 1:00 p.m. is the International Coastal Clean Up Day. Join volunteers from across the county.  Take care of our beautiful coastline by taking part in a beach cleanup.  
  •  WCMB Park Hop Play Date at Gedney Park, Chappaqua :: Moms, dads, and kids of all ages are welcome. Meet some other families and let the kids burn off some steam. Snacks, drinks, and tons of fun will be provided. 

September 16

  • Muscoot Farm, Katonah :: Come and see the magical world of fairies on this fairy-themed scavenger hunt at Muscoot Farm. Costumes are encouraged! Junior volunteers will be on hand with a glittery arts and crafts project as well from 12:00 p.m. – 3:00 p.m. More info at muscootfarm.org

September 22

  • McLean Avenue, Yonkers :: From 12:00 – 7:00 p.m. join The 8th Annual McLean Fall Festival. Rides, games, vendors, food and fun abound at this fall festival. Free parking available with a shuttle service.
  • Waterfront Park, Dobbs Ferry :: Dobbs Ferry is hosting a huge food festival featuring some of the best the lower Hudson Valley has to offer in its beautiful waterfront park with Rivertown Public Market. Lots of family activities and a gorgeous view of the Palisades! Bring empty bellies as well as cash, as not all vendors will take cards. More info at rivertownpublicmarket.com

September 23

  • Jay Heritage Center, Rye :: 11:00 a.m. – 3:00p.m. it’s Jay Day! Celebrate Autumn and American culture and traditions with pony rides, food, and fun. Kids will enjoy face painting and games. Many of Westchester’s popular food trucks will be onsite. Price is $40 per family or $10 per individual.

September 29

  • South Greeley Avenue, Chappaqua :: 10:00 a.m. – 4:00 p.m. Chappaqua’s Children’s Book Festival is the place to be. This free event is for the young reader in your family. Spend the day with 90 authors, activities, a bubble bus, food and more.

September 29-30

  •  205 Business Park Drive, Armonk :: The Armonk Outdoor Art Show transforms a field in the Armonk Business Park into a massive art gallery. One of the top annual judged competitions in the United States, artists travel from all over the country side to show their work, and chat with festival goers. Great deals to be had. Lots of food. And a ton of children’s activities for your young artist. More info at armonkoutdoorartshow.org

September 30

  • Glen Island Park, New Rochelle ::  From 11:00 a.m. – 5:00 p.m. join the Westchester County Car Show. Come see some amazing cars with over 100 trophies to be won. Spectators are free and parking is $5.

What other fun events are going on around Westchester County this month? Let us know in the comments!

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Kristen is the proud mom of two wonderful, smart and sassy daughters (born in 2007 and 2011). Raising her kids as a single mom is a challenge and an adventure and she loves every minute of it. Kristen loves bringing up her girls in the same area of Westchester that she grew up in, having only moved a few miles from her childhood home. A long time passion for working with children led Kristen to pursue a career in education and she has been an elementary school teacher in the Bronx for over a decade. Her teaching career has taught her that every day is a new experience and to "expect the unexpected." If she can find any spare time between teaching and motherhood, Kristen likes to read, binge watch horrible romantic comedies on TV, bake, and go on road trips with her girls.


  1. The Lewisboro Library Fair is Saturday, September 22 from 10 am to 4 pm at Onatru Farm Town Park (99 Elmwood Road in South Salem). The Fair features huge Book, “Attic Treasures” and Toy sales, food, music, vintage cars, a revamped games area, a Gnome Scavenger Hunt(!) and local vendors.

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