20 Fall Festivals Happening in Westchester County

Fall Festivals Happening in Westchester County
Chappaqua Children’s Book Festival

Fall Festivals Happening in Westchester County

Fall is in the air. We can’t wait to make the most of this season by enjoying the incredible line-up of fall festivals. From arts’ festivals to live music to crafts and carnivals, you’ll enjoy celebrating all things fall at these family-friendly events.

Check out these Music Classes for Kids in Westchester

September Fall Festivals

Saturday, September 2nd from 11:00am-5:00pm
2023 Arts & Crafts Hudson River Festival

Enjoy a celebration of arts and crafts at the annual outdoor Hudson River Arts & Crafts Festival. Located on Croton’s Senasqua Park, families can check out jewelry, pottery, sculpture, paintings, photographs, books, embroidery, woodworking, multimedia artworks, gnomes, and more. The event includes free admission and free parking. Senasqua Park, 2 Elliott Way, Croton-On-Hudson, NY. 

Friday, September 8th-Sunday, September 10th from 10:00am – 5:00pm, entry on the half-hour.
Fall Crafts at Lyndhurst

Enjoy a weekend of fall crafts as you enjoy Lyndhurst’s 67 acres of lush landscape. Meet over 200 craftspeople and artisans who will be selling original fashions, accessories, and jewelry, ceramics, fine art painting, printmaking, drawing, and photography. The festival also has food trucks and tastings from local distilleries, wineries, and cider houses. Tickets are $12 for adults; $11 for seniors; $4​ for kids 6-16 and free for kids under six. The event is rain or shine. Parking is free. 635 South Broadway, Tarrytown, NY 10591.

Mount Kisco SeptemberFest

Friday, September 8th-Sunday, September 10th, various times
Mount Kisco SeptemberFest

Mount Kisco’s three-day block party and carnival offers fun and activities for the whole family. Enjoy rides, food trucks, live entertainment, a street fair, a beer garden, and much more! Downtown Mount Kisco, South Moger Avenue, Mount Kisco, NY 10549. 

Sunday, September 10th from 10:00am-5:00pm
SeptemberFest Street Fair

Visit Nyack for their annual SeptemberFest Street Fest! Enjoy live bands, great food, and 200 vendors, selling handmade crafts, jewelry, gifts, and more. Rain or shine. Downtown Nyack, NY, Main St & Broadway, Nyack, NY. 

Sunday, September 10th from 11:00am-5:00pm
New Rochelle Street Fair

Celebrate the 10th anniversary of the New Rochelle Street Fair with live music, crafts, food, and shopping from 200 local vendors. There will also be a Touch-a-Truck section, inflatables, and a beer garden. North Avenue between Winthrop and Fifth Avenues, with an expanded area on Hamilton Avenue to Beaufort Place. New Rochelle, NY. 

Sunday, September 10th from 12:30pm-7:30pm
JazzFest 2023: White Plains Jazz & Food Festival

Enjoy this fusion of music and food in White Plains. The event includes an impressive roster of featured jazz artists such as Westchester Center for Jazz & Contemporary Music, Richie Goods and Chien Chien Lu, Endea Owens and the Cookout, and Mount Vernon’s  Mike Phillips. All music is free. Mamaroneck Avenue White Plains, NY 10601.

Wednesday, September 13th-Sunday, September, 17th, various times
San Gennaro Feast of Yorktown

Enjoy a delicious feast, live music, and a statue procession (on Wednesday, September 13th) at the  San Gennaro Feast of Yorktown. The event also includes rides, games, wine, and beer. Commerce Street and Railroad Park, Yorktown, NY.

Saturday, September 16th from 12:00pm-6:00pm
Oz Land Festival

Follow the yellow brick road to the Oz Land Festival in Peekskill. The event includes a viewing of the classic film. Plus, dancers, live music, vendors, and more. South Street, Peekskill, NY 10566

Saturday, September 23rd from 11:00am-7:00pm
Hudson Valley Irish Fest

Enjoy Irish music and step dancing on the beautiful banks of the Hudson River just steps away from Metro North Peekskill Station! Line-up includes performances by Shilelagh Law, Mundy, Aoife Scott, and more. Peekskill Riverfront Green Park, 50 Hudson Avenue, Peekskill, NY. 

Saturday, September 23rd from 12:00pm-7:00pm
Yonkers River Fest

Families will enjoy three stages of live music at this fun outdoor festival. This includes three stage of live music, a kids’ zone, tons of food vendors, beer gardens, arts and crafts vendors, artists, local organizations, elected officials, and more! 1 Larkin Plaza Yonkers NY 10701.

Saturday, September 23rd from 12:00pm-10:00pm
Toonerville Music Festival 

The 3rd Annual Toonerville Music Festival features live music from the Spin Doctors and 12 other stellar acts, performing on two-stages. The event is a fundraiser for the Pelham Civic Association, an organization dedicated to supporting the community of Pelham. Additionally, the event is $55 per person; $30 for seniors 65 and older and students ages 12-18. Admission is free admission for children younger than 12. Pelham Municipal Lot 7, 195 Sparks Avenue, Pelham, NY

Fun at the Chappaqua Children’s Book Festival
Fun at the Chappaqua Children’s Book Festival

Saturday, September 30th from 10:00am-4:00pm
Chappaqua Children’s Book Festival

The 10th Annual Chappaqua Children’s Book Festival kicks off on September 30th. This year will be headlined by Mary Pope Osborne, author of The Magic Treehouse Series as well as 180 renowned children’s book authors and illustrators. The fun event includes book signings, readings, illustrator demos, with a percentage of proceeds going to literacy programs throughout Westchester and Metro New York. Food will be also available from gourmet food trucks and access to the nearby Chappaqua Farmers Market. Admission and parking are free and the event is held rain or shine. Chappaqua Train Station, Allen Place, Chappaqua, NY 10514. 

Saturday, September 30th from 11:00am-7:00pm
Meet Me on McLean

Celebrate all things fall at this popular Westchester event. The festival includes rides, live music, a beer garden, food trucks, games, and much more! McLean Avenue, between Woodlawn Avenue & Aqueduct Avenue

Saturday, September 30th from 1:00pm-5:00pm

Enjoy a feast of German food and beer as well as cider and hot chocolate for kids. The fest also includes dancing to Bavarian music, live music, and more! Kingsland Point Park, 299 Palmer Avenue, Sleepy Hollow, NY 10591. 

Fun for the whole family at the Armonk Outdoor Art Show
Fun for the whole family at the Armonk Outdoor Art Show

Saturday, September 30th-Sunday, October 1st from 10:00am-5:00pm
Armonk Outdoor Art Show

Art collectors will love exploring and soaking in a collection of art at the annual Armonk Outdoor Art Show. Celebrating its 60th year, view the original work of over 160 artists from around the world. The event also includes food and beverages and free children’s activities such as art lessons and interactive projects during the show. Additionally, families can enjoy local family-friendly experiences from Rye Art Center, DIY Slime, Abrakadoodle, Eduthroughart, Masha Dasha Designs, and Homegrown Gardens. 205 Business Park Drive, Armonk, NY

October Fall Festivals

Saturday, October 7th from 1:00pm-6:00pm
Pound Ridge Harvest Festival

Rock out in Pound Ridge at the annual Pound Ridge Harvest Festival with live music from Galactic. Additionally, the festival also includes a root beer garden, rides, local vendors, inflatables, crafts, games, and prizes. Local restaurants, specialty food purveyors, and a craft beer garden add to the “Oktoberfest feel” of the event. Parking is $25 per car in advance and $30 on the day of the event (space permitted). Pound Ridge Town Park, Westchester Avenue, Pound Ridge, NY 10576. 

Sunday, October 8th from 10:00am-5:00pm
Nyack’s Famous Street Fair

Enjoy the ultimate family foodie festival at The Nyack Famous Street Fair. Located in downtown Nyack, the event includes 250 exhibitors with arts, crafts, retail, home decor, live music, shopping, and food. Additionally, the event is free and held rain or shine. Downtown Nyack, Main Street & Broadway, Nyack, NY 10960. 

Saturday, October 8th-Sunday, October 9th from 10:00am-5:00pm
42nd Annual Outdoor Arts Festival

Held at the Bruce Museum, this popular outdoor festival features the work of artists and craftspeople throughout the country. Here, you can view new works from artists. This includes handmade crafts, jewelry, wearable fiber, glass, furniture and housewares, pottery, and much more. The event also includes interactive demos and food. Admission for the festival is free. Check out the Bruce Museum’s website for the complete artist list. 1 Museum Drive, Greenwich, CT 06830

Saturday, October 14th from 12:00pm-5:00pm
Fall Family Festival

Enjoy a day of quintessential fall moments with a pumpkin patch, pumpkin painting, a bubble zone, and more. $35 per child; adults are free. The Barley Beach House, 95 Dearborn Avenue Rye, NY 10580.

Saturday, October 21st-Sunday, October 22nd, various times
Westchester Craft Crawl

This interactive crafting experience allows artists and art lovers to connect. During the course of the weekend, artists open their studios where patrons can visit over 50+ professional artists at four tour stops between Ossining and Croton. In addition, check out their website for the latest on the stops and featured artists. Various locations.