October Fun for the Whole Family with these Awesome Westchester Events

October Fun for the Whole Family with these Awesome Westchester Events

October is one of our favorite months. The crispness in the air, the beauty of the changing of the leaves, apple picking, and all things Halloween really make this month special. October is also packed with tons of festivals and family-friendly events like the Armonk Outdoor Art Show, the Pound Ridge Harvest Festival, Dia de Los Muertos at Carmoor, The Legend: Cirque Performance in Sleepy Hollow and much more!

Read on to check out these cool events to get on your radar this fall!

Enjoy the Magic of The Great Jack O’Lantern Blaze

This fun Halloween event takes place from September 15th-November 19th (that’s 54 nights!) where you and your family can look at over 7,000 illuminated and hand-carved pumpkins, along with original music, at the historic Van Cortlandt Manor, an 18th-century estate .This walk-through experience is around 45-minutes where you and your family will enjoy bright and creative pumpkin displays such as the Statue of Liberty, a Pumpkin Planetarium, a working carousel, and much more.

This year, families can also enjoy a new pumpkin Ferris wheel, a circus sideshow, and a Jack O’Lantern tribute to the Day of the Dead. Plus, enjoy fall-themed treats, snacks, and drinks at their nearby Café Blaze and on-site store with Halloween and Blaze-related items for sale.Times for the Blaze-Hudson Valley range from 7:30pm-10:30pm. Tickets start at $37 for adults and $29 for kids ages 3-17. Children 2 and under are free. Van Cortlandt Manor, 525 South Riverside Avenue, Croton-on-Hudson, NY 10520. 

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

Attend the 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. Held from Saturday, September 30th-Sunday, October 1st from 10:00am-5:00pm.  205 Business Park Drive, Armonk, NY.

Rock out at Pound Ridge Harvest Festival

Enjoy live music at the annual Pound Ridge Harvest Festival featuring 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. 

Check out the Fall Family Fest

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.

Visit Pumpkin World

Held from September 29th-October 31st, Pumpkin World is a new interactive family-friendly fall event taking place in Rockland County! During this multisensory evening event, families can enjoy an illuminated Jack O’ Lantern walking trail with hand-carved pumpkin art sculptures, live pumpkin carving demonstrations, pumpkin carving competitions, and more. Additionally, families will also participate in technology-infused scavenger hunts, see live entertainment, play games, and enjoy fall-themed treats. All ages welcome; free for kids under age two. Clover Stadium, 1 Phil Tisi Way, Pomona, 10970. 

Support Local Artists at the Westchester Craft Crawl

This interactive crafting tour allows artists and art lovers to connect. During the event, artists open their studios over the course of two where patrons can visit over 50+ professional artists at four tour stops located between Ossining and Croton. Check out their website for the latest on the stops and featured artists. Various locations.Saturday, October 21st-Sunday, October 22rd.

The Legend: Cirque Performance

See The Legend: Cirque Performance

See an adaptation of Washington Irving’s iconic ghost story, “The Legend of Sleepy Hollow” with narration by Washington Irving as a hologram. Along with Irving, families will see death-defying stunts and incredible acrobatic work performed by Westchester Circus Arts. The event is for ages 8 and up. Tickets range from $44-50 dollars per person. Westchester Circus Arts at the Village of Sleepy Hollow, 60 Continental Street, Sleepy Hollow, NY.

Visit Lilymoore Farm for a Very Fluffy Halloween: Take a road trip to Pleasant Valley to Lilymoore Farm to enjoy a Very Fluffy Halloween. The event includes a 1.5 hour guided farm tour where you and your family can meet their alpacas and goats, all dressed in Halloween costumes. Plus, enjoy crafting at the end of the tour. Tickets are $22.95 for adults; $18.95 for kids ages 11 and up; $18.95 for kids ages 2-10; and free for kids two and under. 21 Moore Road, Pleasant Valley, NY 12569. https://www.lilymoorefarm.com/

Paddle as a Witch on the Hudson River

Paddle as a Witch on the Hudson River

Celebrate the witchy season Sleepy Hollow style at the SUP Witch’s Festival. During this 4th annual festival, participants (aka witches) paddle off at Horan’s Landing and around the Hudson. You can also watch or stroll along the riverwalk to watch the witches pass. The event also includes local vendors, brews, and spooky views. All who are paddling must wear a costume. The event is $30 if you’re bringing your own SUP equipment (kayaks welcome) or $45 to rent SUP equipment (includes board, paddle, leash, PFD). All guests interested in participating must pre-register in advance. Sunday, October 15th from 12:00pm-4:00pm, Rain date: October 22nd. Horan’s Landing, 57 River Street, Sleepy Hollow, NY 10591.

Experience the Legend of Sleepy Hollow Family Storytelling Event

Listen to actor/storyteller David Neilsen retell Washington Irving’s, The Legend of Sleepy Hollow. This fun family event also includes Halloween treats and activities. The event is limited to 40 seats and designed for kids ages 8 and up. Tickets are $10 for adults and $5 for children. Held on Sunday, October 22nd, readings are offered in two blocks at 11:00am or 12:30am. Hudson Valley Writers Center, 300 Riverside Drive, Sleepy Hollow, NY 10591. 

Experience Hulda’s Night at Rockefeller State Park Preserve

Enjoy a Halloween experience like no other with Hulda’s Night. The event starts by walking through a path illuminated by lanterns until you join a traveler. Your journey continues as you listen to more stories about war and a witch living nearby. Your group goes down to the witch’s spring trail as you are guided to Hulda’s home, eventually meeting Hulda herself who tells your group a story. Tickets are $30.00 per person. The experience takes place from October 18-21st and October 25th-28th. Rockefeller State Park Preserve, 25 Sleepy Hollow Road, Sleepy Hollow, NY 10591. 

Enjoy Dia de Los Muertos at Caramoor

Every year, Caramoor throws an incredible Dia de Los Muertos event with live music, dance, crafts, and more. Calpulli Mexican Dance Company will be in attendance as kids and their families learn more about this day and its cultural significance. Held on October 15th at 3pm. The event is free. 149 Girdle Ridge Road, Katonah, NY 10536. 

Roam On Your Own at Lyndhurst Spirited Mansion

Visit Lyndhurst Mansion for their “Roam Your Own Weekend.” Families can visit the mansion without a guided tour, viewing the cool seasonal decorations and taking in the beauty of this historic mansion. This includes viewing the decorated entrance hall, reception room, parlor, library, and Victorian dining room. Refreshments and snacks will be available for purchase on-site.

Tickets are $30 for adults and $20 for kids ages 6-16. All visitors must have a pre-purchased ticket to enter the mansion. Entry begins promptly at the designated time and tickets do sell out. The event is held on Saturday, October 21st; Sunday, October 22nd; Saturday, October 28th and Saturday, October 29th from 10:00am-3:00pm. Lyndhurst Mansion, 635 South Broadway, Tarrytown, NY 10591.

Go Apple Picking

Hooray, it’s cider and apple-picking season! Enjoy a fun weekend with your family at Harvest Moon Farm & Orchard (130 Hardscrabble Road, North Salem, NY 10560); Wilkens Fruit & Fir Farm (1335 White Hill Road, Yorktown Heights, NY 10598), and Stuart’s Fruit Farm (62 Granite Springs Road, Granite Springs, NY 10527).

Attend Applefest

Take a trip to Warwick for a day dedicated to apples at Applefest. Held on October 1st from 9:00am-5:00pm, this event includes live entertainment, music, a kids’ carnival, a farmers’ market, 150 craft vendors, 75 food vendors, an apple pie baking contest, and tons more. 2 Bank Street. Warwick, NY, 10990.

Walk Through a Corn Maze

Visit Wilkens Farm (1335 White Hill Road, Yorktown Heights, NY 10598) or Outhouse Orchards (139 Hardscrabble Road, North Salem , NY 10560) for a fun walk through their impressive corn mazes.

Fall at the Untermyer Gardens Conservancy
Fall at the Untermyer Gardens Conservancy

Attend Family Fun Day at the Untermyer Gardens Conservancy

Spend the day at Untermyer Gardens Conservancy with your family and enjoy a magic show, kit flying, recycled art crafting, a family bird walk, family adventure tours and more. Held on Sunday, October 8th from 1:00pm-4:00pm. 945 North Broadway, Yonkers, NY 10701. 

Visit LEGOLAND Discovery Center Westchester

One of our favorites for indoor fun, this fall they are hosting the Brick-or-Treat Monster Party with monsters taking over the LEGOLAND Discovery Center Westchester. Families can also enjoy a viewing of the 4D Movie, The Great Monster Chase,  spooky Halloween decorations, LEGO® activities, and more. LEGOLAND Discovery Center Westchester, Ridge Hill Mall, 39 Fitzgerald Street, Yonkers, NY 10710, 

Check out the NY Sheep and Wool Festival

Take a trip to Rhinebeck for a special visit to the NY Sheep and Wool Festival. Held from October 21st-October 22nd, the festival features a range of attractions such as kids’ activities, demonstrations, book signings, a livestock display, and more. Dutchess County Fairgrounds 6550 Spring Brook Ave, Rhinebeck, NY 12572.