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Your Awesome Westchester Weekend: October 14-17

Irving's 'Legend' in Irvington
Jonathan Kruk performs Irving’s Legend at Washington Irving’s Sunnyside in Irvington, NY on October 24, 2021.

Your Awesome Westchester Weekend: October 14-17

Halloween is certainly in the air this weekend where you and your family can enjoy a production of the gravity-defining “The Legend,” visit Barton Orchards for the Jack O’Lantern Jubliee, or watch the always-entertaining Irving’s ‘Legend’ in Irvington. This weekend is also all about festivals where you enjoy a host of art and music events at the Serious Fun Arts Festival in White Plains, or your kids can meet their favorite authors and illustrators at the Chappaqua Children’s Book Festival. No matter what you do, we hope you have the best Westchester weekend!

Thursday, October 13th-October 30th, various times
Fall-O-Ween

Bask in the beauty of fall at NYBG! Admire the changing foliage as you watch pumpkins become spooky and spectacular works of art during Pumpkin Carving Face-Offs, set out on nighttime adventures with Spooky Pumpkin Garden Nights, and enjoy sweet treats like pumpkin spice. And don’t miss the Garden’s glorious fall foliage. With tricks and treats aplenty, there’s something for everyone to enjoy. New York Botanical Garden, 2900 Southern Boulevard Bronx, NY 10458-5126

October 12th-October 16th, various times
Serious Fun Arts Festival

Enjoy a week of culture, public art, music, dance, and fun for the whole family at the upcoming Serious Fun Arts Fest in White Plains. Held from October 12th-October 16th, the Serious Fun Arts Fest features over 200 artists whose work will displayed throughout downtown White Plains. This includes public art displays, including a skyscraper-high landmark mural and sculpture installations. Additional highlights include Chamber Music with the Phil Grace, WUZA-WUZA African Music & Dance Ensemble,  Family Fun: Songs From the Middle East with Matt Turk and Friends, Jitterbags: Jazz for Kids, Open Mic Poetry, pop-up dance featuring Steffi Nossen Dance, and so much more! There will also be a performance of “The Prom” at the White Plains Performing Arts Center,  street performances, art making for families with the ArtsMobile at Renaissance Plaza, a Hula hoop and Chinese Fan workshop, a poetry event, and much more. Various locations in White Plains, NY.

Friday, October 14th, Saturday, October 15th and Sunday, October 16th
The Legend

Watch a gravity-defying performance commemorating the 200-anniversary of the legend of Sleepy Hollow with “The Legend.” Running until October 23rd, the show features performers from Westchester Circus Arts that includes a cirque/theatre noir production with narration by Washington Irving himself. Tickets are $33 per person. 60 Continental Street, Sleepy Hollow, NY 10591.

Saturday, October 15th at 9:00am
5K and Kids Fun Run

Kick off the weekend with a family run. After the race, enjoy fall activities such as face painting, pony rides, slides, a book fair, and more. 20 Fifth Avenue, Pelham, NY 10803.

Saturday, October 15th from 10:00am-11:00am
My Superpower Workshop Series

Participate in the interactive and fun superhero series where kids will learn how to understand themselves and the world around them.  There are two groups for ages 3-6 years old and 7-11 years old. Register here. Westchester Children’s Museum, 100 Playland Pkwy, Rye, NY 10580.

Saturday, October 15th from 10:00am-4:00pm
Chappaqua Children’s Book Festival

Enjoy a day of books, literacy, and fun at the annual Chappaqua Children’s Book Festival. The 9th annual event is free and features over 160 children’s book authors and illustrators. This includes multiple genres, reading levels, special presentation, and books for sale. The event is rain or shine. Chappaqua Train Station.

Saturday, October 15th and Sunday, October 16th from 10:00am-6:00pm
Jack O’ Lantern Jubilee

Enjoy a fall festival at the Barton Orchards with Jack O’Lantern Jubliee. The event includes fun on their giant slide, hayrides, a petting zoo, a dog park, pick your own apples, and more! The event is $27 for people ages 13 and over; $15 for children ages 4-12 years old; and children three and under are free. Barton Orchards63 Apple Tree Lane, Poughquag, NY 12570.

Saturday, October 15th from 10:30am-12:00pm
Pumpkin Painting and Carving

Enjoy an afternoon at Hilltop Hanover Farm and select a pumpkin from their patch. You and your family can then decorate or carve them. The event is $15 per person, or $40 for a family of three. Registration is required. Hilltop Hanover Farm, 1271 Hanover Street, Yorktown Heights, NY 10598.

Saturday, October 15th from 1:30pm-2:30pm
Storybook Animals Workshop: Music, Movement, and Theater

Kids ages 5-7 can enjoy an afternoon of singing, dancing, and play. The event includes engaging and imaginative activities that help bring storybook characters to life.  $5 per person. Rye Arts Center, 51 Milton Road, Rye, NY 10580.

Saturday, October 15th from 2:00pm-3:30pm
The Great Bedford History Hunt

Enjoy a fun scavenger hunt with your family as you learn more about Bedford’s past. After the hunt, enjoy cider, doughnuts, and tours. Bedford Historical Society, 612 Old Post Road, Bedford, NY, 10506.

Saturday, October 15th from 3:00pm-5:00pm
Ridgetoberfest

Visit Ridge Hill for an afternoon of family-friendly activities, food, live music, pumpkin carving, and more. There will also be events from retailers such as The Cup, Muse Paintbar, Monster Mini Golf, Healthyholic, and more! Ridge Hill, One Ridge Hill Boulevard, Yonkers, NY 10710.

Saturday, October 15th from 3:30pm-9:30pm
Bedford Music Festival

Rock out with your kids at the first-ever Bedford Music Festival. 90s band, Spin Doctors headlines the show, along with four local bands. Plus, enjoy food, music, and more. Free entry. $20 parking fee per car. John Jay Homestead, 400 Jay Street, Katonah, NY 10536.

Various times until October 31st
Irving’s ‘Legend’ at Sunnyside

Listen to master storyteller Jonathan Kruk recount “The Legend of Sleepy Hollow.” The experience also includes live music from Jim Keyes as well as an appearance from the Headless Horseman. Guests can now enjoy fall-themed drinks, such as beer from Captain Lawrence, 1911’s New York state hard cider, and pumpkin spice soda, as well as fun snacks like fudge, Legend popcorn mix, and cider donuts. The museum shop, which can be visited before or after the event, is filled with souvenirs and local finds, including Legendthemed t-shirts, hats, and more. Washington Irving’s Sunnyside is at 3 West Sunnyside Lane, Irvington, one mile south of the Tappan Zee Bridge.

Sunday, October 16th from 12:00pm-4:00pm
Rain date: October 23rd
SUP Witches Festival

Celebrate the witchy season Sleepy Hollow style at the SUP Witch’s Festival. The 3rd annual festival features a paddle where witches take off at Horan’s Landing and paddle along 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 bringing 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 (registration opens on September 16th). Horan’s Landing, 57 River Street, Sleepy Hollow, NY 10591.

Sunday, October 16th from 2:00pm-4:00pm
Guided Hike at Westmoreland

Enjoy a free, family hike at Westmoreland. Hikers will learn more about the biodiversity, ecosystems, and native wildlife. Limited to 20 people on a first-come, first-served basis. Westmoreland Sanctuary, 260 Chestnut Ridge Road Mount Kisco, NY 10549.

Sunday, October 16th from 1:00pm-4:00pm
Family Science Workshop: Rock, Water, Ice, and Time

Enjoy a weekend of science experiments with your kids at the Hudson River Museum. Ideal for kids ages eight and up, the workshop teaches kids about the forces that have shaped the Hudson River watershed, and then render them in clay. This event is free with general admission. Hudson River Museum, 511 Warburton Avenue, Yonkers, NY 10701.

Have a great Westchester weekend!