October Events in Westchester County {2022}

The weather has cooled down and it’s now the perfect time to embrace all things apple and pumpkin spice. Check out these events taking place in October and starting planning your month of fun.

Comedy:

Levity Live (Palisade Center – West Nyack) Enjoy a comedy show at Levity Live in October. Upcoming shows include Big Jay Oakerson (Oct. 6-8), The Amish Outlaws (Oct. 13), Jessica Kirson (Oct. 14-16), Tony Rock (Oct. 28-30). *Check the site for the full lineup

October 8 (Mahopac) The Uncle Louie Variety Show at Putnam County Golf Course. “The Uncle Louie Variety Show is composed of two hilarious Italian-American comedians, Carlo Russo and Lou Greco. For many years, they have been making people laugh through their unique brand of comedy that brings memories of how it was like to grow up as an Italian.” 7 PM – 9 PM with an intermission. Doors open at 6 PM. Tickets: $45+tax includes an Italian buffet dinner

October 14 (Brewster) Comedy Night at the Funny Farm at Tilly’s Table – “Laugh the Night Away with these 3 Comedians, Patty Rosborough (from Putnam), Frank Favia, and Helene Angley! 3 Times the Laughter, 3 Times the Fun!” Doors open at 6:30 PM, showtime is 8 PM-10 PM. Tickets: $45 + tax/person . Ticket price includes show & buffet dinner. Cash bar available.

Date Night/Girls Night Out:

October 19 (Bedford) Trivia Night Rock Paper Scissors Events presents trivia night at the Bedford Playhouse. 7-8 PM. Teams of up to 6 players. 

Eat & Drink:

Taste of Westchester Cooking Demo Classes(restaurants throughout Westchester County) Enjoy cooking demos from local chefs and then sample their creations.  There are lots of October classes including: Zwilling J.A. Henckels Cooking Studio (Oct.1), La Catena Italian Restaurant (Oct. 3), Baked by Susan (Oct.11), Tredici North (Oct. 12), The Dessertist (Oct. 17), The Taco Project – Yonkers (Oct. 18), Saw Mill Tavern (Oct. 19), Maria Restaurant (Oct. 22), Village Social Kitchen & Bar (Oct. 23), Mima Vinoteca Italian Kitchen & Wine Bar (Oct. 25), The Horse & Hound Inn (Oct. 26), The 808 Bistro (Oct. 29).

October 1-2 (Elmsford) Captain Lawrence Oktoberfest – Enjoy, “beers, brats, music and good times.” Festivities begin around 1pm both days!

October 4 (Mamaroneck) 5 Course Food and Beer Tasting – Join Chef Jessica of Cooking by Jessica and Decadent Ale Beers for a 5 course food and beer tasting. 6:30 PM, $75/person

October 8-9 (Bethel) The Big Sip: A Wine & Spirits Festival – A two-day craft beverage festival celebrating the finest wineries and distilleries in our region with live music from Mike DelGuidice & Big Shot (Saturday), Ripe (Sunday), and more special guests!” Oct. 8 & 9: 1 PM -5 PM, VIP Entry 12 PM, Tickets:$50/Saturday, $45/Sunday VIP Tickets: $90/Saturday, $85/Sunday, Designated Driver tickets available at discounted price, ticket prices will go up the week of the event and the day of.

October 8-9 (Mount Kisco) Captain Lawrence Oktoberfest – Enjoy, “beers, brats, music and good times.” Festivities begin around 1pm both days!

October 9 (Mahopac) Holy Smoke Oktoberfest – 1 PM – 5 PM. Enjoy this all you can eat and drink event on the Great Lawn. Games, giveaways, German beers and more. 21+ event. Tickets must be pre-purchased. Tickets: $100/person + $8.16 fee.

October 9 (White Plains) White Plains Oktoberfest 1-6 PM Live music, games, food and German beer. Taking place on Mamaroneck Avenue between E. Post Rd. and Maple Avenue. Advance tickets $11, day-of tickets $15, Cash and Credit card will be accepted at the door, but all outside bars will be cash only.

October 15 (Wappingers Falls) Grand Slam Beer Festival at Dutchess Stadium, 2 PM – 6 PM, enjoy beer and cider, music, food available for purchase, games and more.Tickets: $107/VIP ticket (1 PM – 6 PM), $82/General Admission (2 PM – 6 PM), $25/Designated Driver, rain or shine, $5 parking fee (free for VIP), 21+ only event

October 15 (Peekskill) Peekskill Brewery 14th Anniversary Block Party 2-8 PM, live music, food trucks, beer tents, vendors, artisans and more.

Fairs & Festivals:

October 1 – (Peekskill) Peekskill Rotary’s 2022 Fall Festival – 12 PM – 6 PM at the Riverfront Green. “This year, there will be live music all day on the main stage, a pumpkin carving design contest with viewing and judging under the gazebo, a bike rodeo for children, food trucks, obstacle course, arts & crafts and more.

October 1-2 -(Armonk) Armonk Outdoor Art Show – Taking place at 205 Business Park Drive, 10 AM – 5 PM, rain or shine. “Approximately 140 juried artists will present work in a broad range of art, including Fine Crafts, Mixed Media, Painting, Printmaking/Drawing/Pastels, Sculpture, Photography/Digital Art, and Wearable Art.” There will also be food, drinks, a Family Activities tent and more. Tickets: $15/General admission, $13/seniors, Free/18 and under.

October 8 (reschedule date) – (Croton-on-Hudson) Village of Croton Fall Fest/Oktoberfest – Grand Street at the Dummy Light 12 PM – 6:00 PM, food trucks, vendors, family fun.

“The Village of Croton is hosting the 2nd annual Oktoberfest featuring food, beer, arts and crafts, music and family fun! It’s the only Oktoberfest in the Hudson Valley with a kid friendly “Kinder Fall Fest” area! The street will be full of food and fest for all ages. Traditional German fare and craft beers, as well as international offerings from a wide variety of local spots! Plenty of other non food related vendors too. Come help us make this Croton Oktober/Fallfest a fun day! In Vassallo Park there will be a more youth oriented Fallfest, with food and music so the kinders can get their fest on too.”

October  8 – (Tymor Park, Lagrangeville) Dutchess County Irish Festival – Presented by the Dutchess County Gaelic Athletic Association. Live music, food and drinks, kids inflatables and more. 12 PM – 9 PM. Adult admission: $23.04/adult (includes $3.04 fee), Free/18 and under

October 9 – (Jefferson Valley Mall) Yorktown Fall Festival and Car Show 11 AM – 5 PM Enjoy a day filled with music, food, children’s rides, musical performances and more.

October 12-16 (White Plains) Serious Fun Art Festival – This festival runs through five days, “this fall with arts activities ranging from concerts to live mural painting, a public art walking tour to dancing in the streets. There will be sculpture, performance art, massive public art unveilings by renowned artists, fun family art-making and more throughout the downtown. Don’t miss Sunday’s headliner concert with Sammy Rae and Friends. And reserve your spot for Saturday’s FREE Serious Fun Block Party, with an eclectic mix of six inspired performances!” Check out the link above for the full schedule and to purchase tickets.

October 13 (Tarrytown) Harvest Party for Sukkot – Thurs. Oct. 13 from 5:30-7:30 PM at the Shames JCC in Tarrytown. “Come celebrate the fall harvest with the live bluegrass sounds of @nefeshmountain founders Doni + Eric while you nosh on an abundant, seasonal (and vegetarian!) graze board designed by local chef @katesonders. Sukkot is an annual Jewish agricultural festival that asks us to rejoice in mother earth’s bounty – so rejoice we will….The party will be outdoors and all are welcome. (Bring your instruments if you want to jam along!)” $18/members, $30/non-members

October 15 (Chappaqua) Chappaqua Children’s Book Festival – Taking place at the Chappaqua Train Station fro 10 AM – 4 PM. “Free outdoor festival celebrating children’s books and authors. 158 authors plus a family fun zone, food trucks, entertainment, the Bubble Bus and more. Books available for sale and signing — cash and credit cards. Come and spend the day in downtown Chappaqua. Free parking.”

October 15 (Scarsdale) Greenbugh Nature Center Fall Festival – “Outdoor fall celebration for families and visitors of all ages featuring live music, crafts and games, a pumpkin and scarecrow walk, apple cider demonstrations and tastings, vendors selling sustainable items, meadow dedication, and more. 10AM-3PM.”

October 15 (Katonah) Bedford Music Festival at the John Jay Homestead – The Spin Doctors will be the headline band with other local bands playing throughout the day. Enjoy “food from local restaurants, retailers, and vendors showcasing their extraordinary fare and unique merchandise.” 3:30 PM – 9:30 PM, Free entry, $20/car parking fee.

October 15 (North Salem) North Salem Arts & Food Festival – 10 AM – 3 PM, “This is a free event with artisan goods, music, kids activities, food, & open artist studios throughout the hamlet.”

October 15 (Yonkers) Ridgetoberfest – 3 PM – 7 PM, “enjoy an afternoon of family-friendly activities, culinary delights, beer, live music, pumpkin carving and more!” This event will be taking place on Market Street.

October 22-23Westchester Fall Craft Crawl -10 AM – 5 PM, “A free artist-organized outdoor studio tour featuring 54 professional craft artists over 4 tour stops in Ossining & Croton-on-Hudson.” rain or shine.

Family Fun:

October 2022 – January 2023 (FDR State Park, Yorktown Heights) Harry Potter: A Forbidden Forest Experience – “A nighttime woodland trail experience filled with magical creatures and wizarding wonders from the Harry Potter™ and Fantastic Beasts™ films. Explore after dark the sounds, lights, and special effects that bring the magic of the Wizarding World to life. Guests will also be able to enjoy a wide range of delicious food and drinks at the village! Set in a beautiful woodland, this nighttime trail experience has been created by award-winning theatrical designers and experiential creators.” Parking: $8/online, $10 on-site, Tickets: Adults (16+) $46-$75 + $9.00 booking fee (depends on date), Child (5-15) $35-$64 +$9.00 booking fee (depends on date)

October 1-2 (Scarsdale) Run Wild at Greenburgh Nature Center – “Run Wild is a forest run and obstacle course where you can enjoy some friendly competition while getting active out in nature. Best for ages 5-15. This is a rain or shine event!” 9 AM -2 PM, 30-minute time slots. $25/runner

October 1 (Ossining) Insect Sweeping at Swope’s Field – Teatown, 1 PM – 3 PM, “Join Early Childhood Art Educator and insect enthusiast Caroline Erb for a sweep net session in Swope’s Field. What invertebrates will we find in the tall grass? Make your own sweep net and then test it out. This program involves walking in tall grass, so please wear long pants and socks. Meet at the Nature Center.” Members: $10/family, Non-Members: $15/family, limited to 5 families.

October 2 (Ossining) Color Hike – Teatown, 10 AM -12 PM, “Start the season with an autumnal color hike, where we’ll look for the full rainbow of fall foliage. Be prepared for a moderately difficult hike through Hidden Valley. Wear appropriate hiking footwear, bring sun protection, bug spray, water, and a snack.” Members: $3, Non-members: $8, limited to 15 participants, recommended for ages 8+

October 2 (Bronx River Parkway) Bicycle Sundays -10 AM – 2 PM, “the parkway is open exclusively for bicyclists, in-line skaters, scooters, walkers and joggers from Exit 22 at the Westchester County Center to Exit 4 at Scarsdale Road in Yonkers. The round-trip distance is 13 miles. The road is closed to automobiles in that stretch of parkway. Admission is free and free parking will be available in the East Lot at the Westchester County Center.”

October 8 (Ossining) Natural and Native Crafts – Teatown, this program will take place at Cliffdale Farm, 10 AM -11 AM and 2-3 PM. “Learn skills essential for historical Lenape children with Early Childhood Art Educator Caroline Erb. Try your hand at weaving phragmites mats, create a corn husk doll, and make rope from plant fibers. We will also play traditional games.” Members: $10/family, Non-members: $15/family, limited to 5 families

October 21 (Croton Point Park, Croton-on-Hudson) Westchester County Parks Screening Under the Stars. The Addams Family 2, 2021 (PG) Croton Point Park. Movie begins at sundown. Refreshments for sale. Bring blanket or chairs. Parking and admission free.

October 22 (Ossining) Take a Hike, Make a Memento – Teatown, 1 PM – 3 PM, “We often say, “take a hike, leave only footprints,” but during this program, we invite you to gather natural materials as we walk to fashion into art inspired by your journey. Be prepared to get messy: mud makes for great natural pigment!” Members: $10/Family, Non-members: $15/family, limited to 5 families.

October 23 (Ossining) Misunderstood No More – Teatown, 11 AM – 12 PM “Spiders, snakes, bats, and bugs! So many different animals get a bad rap due to age-old superstitions and stories. Teatown’s myth buster, Elissa Schilmeister, will share her knowledge of the importance of all these animals for a healthy world. There will be plenty of opportunities to touch some of these misunderstood creatures.”

Live Music & Performances:

Bethel Woods: (Bethel) A little further to travel but some great musicians worth checking out play here. In September you can see: 1, 2, 3 Andrés: Outdoor Family Concert (Oct. 22) *Check the site for the full lineup

Caramoor: (Katonah) This month performances at Caramoor include singer Kat Wright (Oct. 14), a FREE Celebrate Día de los Muertos event (Oct. 16), Sierra Boggess (Oct. 22), Evnin Rising Stars program (Oct. 29-30). *Check the site for the full lineup

The Capitol Theatre: (Port Chester) This month’s lineup includes: Pace Women’s Justice Center Benefit Concert featuring Sara Bareilles (Oct. 6), Jeff Beck (Oct. 7-8), Phil Lesh & Friends (Oct. 14-16, 21-23, 28-31), ZZ Top (Oct. 18) *Check the site for the full lineup

Emelin Theatre: (Mamaroneck) This month’s lineup includes The James Hunter Six (Oct. 2), Ladies of Laughter (Oct. 15), Glenn Miller Orchestra (Oct. 16), Carole and Paula in The Magic Garden (Oct. 23) *Check the site for the full lineup

Paramount Hudson Valley: (Peekskill) October’s lineup includes: The Royal Scam: A Steely Dan Celebration (Oct. 1), Broadway’s Rock of Ages Band (Oct. 7), Accept (Oct. 22), Tracey Morgan: No Disrespect Tour (Oct. 27), Rocky Horror Picture Show with the Apoca-Lips Cast (Oct. 29) *Check the site for the full lineup

Tarrytown Music Hall: (Tarrytown) October’s lineup includes: The Wood Brothers (Oct. 5), Violent Femmes (Oct. 8), The Wailers: 2022 One World Tour (Oct. 12), Hollywood Nights: The Bob Seger Experience (Oct. 15), Paula Poundstone (Oct. 21), The Rocky Horror Picture Show (Oct 21), Pink Talking Fish (Oct. 22), The Mavericks (Oct. 28 & 29) *Check the site for the full lineup

October 7 – 23 (White Plains) – Check out the Prom at The White Plains Performing Arts Center. “A musical comedy about big Broadway stars on a mission to change the world and the love they discover that unites them all. When they hear that trouble is brewing around a small-town prom, they know that it’s time to put a spotlight on the issue, and themselves.” Performances begin October 7th at 8 PM and run through October 23.  2:30 PM and 8:30 PM on select dates. Tickets: $45-$62 each.

October 7 – (Jefferson Valley) Dueling Pianos at Club Fit Jefferson Valley. “Two Pianos. Two Singers. Tons of Comedy. One Great Show. The performers belt out an all-request, rock and roll singalong while you and your guests dance and sing to this show that’s part music, part comedy and all fun.” 7 – 10 PM, doors open at 6 PM,  $25 members, $35 non-members. Ages 21+ only.

October 22 – (Mahopac) Christian Guardino at Putnam County Golf Course – “Christian Guardino is a 21-year-old singer/songwriter from Patchogue, NY. You may recognize him from his time on “America’s Got Talent” where he received Howie Mandel’s Golden Buzzer. Christian also won Amateur Night at The Apollo,and appeared on Fox’s “Showtime at The Apollo” with host Steve Harvey.” Show starts at 7 PM, doors open at 6 PM. Cash bar and snacks available for purchase. This is an indoor concert. Tickets: $31.43 – $53.10.

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