It's time for fall family fun in Armonk - Chappaqua - Mount Kisco - Pleasantville and we can hardly wait! We are lucky to have so many fall attractions and events in Westchester County and the Hudson Valley where families have been making fall memories for years. From picking apples to leaf-peeping to Oktoberfest fun ... Macaroni KID Armonk - Chappaqua - Mount Kisco - Pleasantville has all the details for you and your family to make the most of autumn in Westchester County and beyond.
Updated 10/20/23
Our new 2023 MacKID Guide to Fall Fun in Westchester County comes to you with thanks to The Armonk Outdoor Art Show! Read more about this annual tradition here!
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Farms, Orchards, and Markets in Westchester County and the Hudson Valley |
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 | Apple Picking in Westchester County and Beyond |
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Leaf Peeping in Westchester County and Beyond |
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Rockefeller State Park Preserve
125 Phelps Way, Pleasantville
Details: Crushed stone carriage roads serve as the wide and walkable trails through woods and pastures, past lakes, streams, and rock outcroppings. Bring the carrier for smaller ones, as this is not a particularly stroller friendly walk, although it is ideal for toddlers to explore.
Westmoreland Sanctuary
260 Chestnut Ridge Road, Mount Kisco
Details: Well marked and well maintained trails great for hiking with families (although you will want the carrier again!). Beautiful views and lots to explore from Betchel Lake to the playhouse to the Fern Garden. There are many routes to choose from depending on the type of adventure you would like for the day.
Marsh Sanctuary
B Road, Mount Kisco
Details: The Marsh Sanctuary is a 156-acre nature preserve with trails, open space, a community garden, and a commitment to the protection of wildlife. It is home to the largest freshwater marsh in Westchester County. Lots of wildlife, a pond, wooded areas, and views.
155 Millwood Road, Chappaqua
Details: Take a walk in the woods at Gedney Park and immerse yourself in spectacular fall foliage. Family friendly with some opportunities for stroller walking if you still to the paved path which is still quite nice. Bathroom facilities, a pond, and two playgrounds make it a perfect day out.
Willing to take a drive or looking for a weekend getaway? You'll love our Leaf Peeping and Fall Foliage Guide to New York State!
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Westchester County and Hudson Valley Fall Attractions: |
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The Great Jack-o-Lantern Blaze
Van Cortlandt Manor
525 S Riverside, Croton-on-Hudson, NY 10520
From September 15th - November 19th the Van Cortlandt Mansion is illuminated with the magic of over 7,000 pumpkins. This annual tradition is a long-time family favorite for Westchester County and Hudson Valley residents. Tickets sell out quickly!
The Hudson Valley Shakespeare Festival
Garrison
This summer favorite lasts through September 17th with the showing of Penelope. The new location is beautiful for a fall evening picnic prior to the show as the river views never disappoint. Better suited for families with tweens and teens.
New Exhibit at Greenburgh Nature Center: Dino Dig
Scarsdale
September 7th - October 22nd
This Dino Dig Exhibit is open from Tuesday through Sunday at the Manor House and costs $5 per child. 10:30 a.m. - 4:00 p.m.
Renaissance Faire
Tuxedo Park
Step back in time on the themed weekends from the end of August through October 8th. Rides, food, entertainment, and gifts for the whole family.
Lyndhurst Mansion - Fall Classic Mansion Tour
Tarrytown
October 14 - 28
Enjoy the grounds daily through December between 9:30 and 4:30 or take one of the guided tours.
Fall events in Westchester County |
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Macaroni KID Armonk - Chappaqua - Mount Kisco - Pleasantville is adding fall events regularly as we find them, so check back often for updates!
September
September 8: Ardsley Food Truck FestivalSeptember 8 - 10:September 8 - 25: Circus Vazquez at Garden State PlazaSeptember 9:- *Pubilsher's Pick: Rewilding School Fall Festival - Enjoy a unique festival event that celebrates the natural beauty of the Marsh Sanctuary as expert guides lead family groups through foraging, shelter-building, foam-tipped archery, fire making, and more!
- Briarcliff Manor Community Day with Toddler Town by Macaroni KID from 4 p.m - 7 p.m. at Law Park!
- New Castle Community Day
- Town of Cortlandt Town Day
- City of White Plains Truck Day
- Lewisboro Library Fair
- Bedford Fire Department Parade, Party and Fireworks
- Rye Food Truck Festival
September 9 - 10:September 10:Armonk Cider and Donut FestivalOssining Hispanic Festival, Market Square 12 p.m. - 7 p.m.
September 13 - 17: Yorktown's San Gennaro FeastSeptember 14: Bluegrass at the Farm, North SalemSeptember 15:September 15 - September 25: Flip Circus at Danbury Fair MallSeptember 16:September 17:September 20 - 24: Ardsley Volunteer Fire Department Carnival at Louis Pascone ParkSeptember 22:- The Ghost of Sleepy Hollow at Whippoorwill Theater (ages 8+)
- Greenburgh Nature Center Family Movie Night: Moana
- Fall Family Gathering: A Celebration of our Diverse Community, 4:30 - 6 p.m., Horace Greeley Courtyard, Chappaqua
September 22 - 23: Giant Tag Sale, Mount KiscoSeptember 23:Village-Wide Tag Sale at Village of Croton-on-HudsonPleasantville Block Party (rescheduled to 9/30)Rye Children's Book Festival at Westchester Children's Museum2023 Hudson Valley Irish Fest, PeekskillFiesta! A Bilingual Concert Experience with Flor Bromley at Ossining Public Library, 3 p.m.Puppet Show at Mount Pleasant Library: The Three Little Pigs 10:30 a.m.
September 23 - 24:September 23 & 30: Soul Brewing Company OktoberfestSeptember 24:September 30 - October 1:September 30:Armonk Outdoor Art Show: Publisher's Pick for family fun! Enjoy complimentary tickets for children under 18 and an interactive and engaging Kids Zone for all kinds of little artists.Family-Friendly Screening: The Witches (PG) at Jacob Burns Film CenterChappaqua Children's Book Festival: Publisher's Pick for family fun! Free entry, bubble bus, kids' activities, largest book festival on the east coast!Mamaroneck Monarch Butterfly FestivalWelcoming Fall Sidewalk Sale, HartsdaleTown of Mamaroneck Food Truck FestivalFCC and Temple Beth El Fall Funfest, Chappaqua, 5:30 p.m. - 8:30 p.m.
October
- September 29 - October 31: Pumpkin World: Where Jack O’Lanterns Glow, Pomona, NY
October 1:Armonk Outdoor Art Show: Publisher's Pick for family fun! Enjoy complimentary tickets for children under 18 and an interactive and engaging Kids Zone for all kinds of little artists.Dashing for Dylan Challenge & Family Fun Day, Rye Brook Publisher's Pick for family fun!Somers Annual Women's Club Tag SaleThe Paramount at Somers Fall Festival 12 p.m. - 4 p.m. Rain or shineBronxville Free Fall Festival at Village Hall, 12 - 4 p.m. (raindate October 8th)Mount Pleasant Street Fair, Elwood Ave 1 p.m. - 6 p.m. (raindate October 8th)Dig into Archeology Day at Croton Point Nature Center 11 a.m. - 4 p.m.Broadway Fright Night, Peekskill Paramount 7 p.m.
October 6: Greenburgh Nature Center Family Movie Night: EncantoOctober 6 - 8: Our Lady of Shkodra Albanian Church Carnival, HartsdaleOctober 7:3rd Annual Croton-on-Hudson Oktoberfest - rescheduled to 10/14Pound Ridge Harvest Festival - cancelledHorah with the Torah at Chabad of the RivertownsSimchat Torah Celebration at Chabad of the RivertownsSleepy Hollow Emergency Services Open House - 10 a.m.
October 7 - 9: Indigenous Peoples Day Free 24-Hour Celebration, Randalls Island NYCOctober 8- White Plains Oktoberfest
- Kiwi Day Camp Fall Festival
- Family Fun Day at Untermeyer Gardens
- Yorktown Fall Festival and Car Show 11 a.m. - 5 p.m.
- The Mount Kisco Italian and Hispanic Heritage Celebration and Car Show, Library and Village Hall 12 p.m. - 6 p.m
October 9: Dean Pond Somers Fall Family Day 11 a.m.October 12 - 16: Serious Fun Arts Fest, White PlainsOctober 14 - 28: Fall Classic Mansion Tour, Lyndhurst MansionOctober 14Pelham Children's Center Pumpkin Festival + Fundraiser 5k and Book SaleCamanchaca: Music of the Andes, Ossining Public Library, for adults and teens 2 p.m.Harvest Moon Orchard Fall Festival15th Anniversary Block Party, South Water Street Peekskill 12 p.m. - 6 p.m.Mount Pleasant Recreation Fall Foliage Festival - Free family event, 11 a.m. - 3 p.m. Broadway FieldSt. John's Church Harvest Fair, Tuckahoe - 10 a.m. - 3 p.m., FreeRidgetoberfest Ridge Hill, Yonkers 3 p.m. - 7 p.m.Circle School Kids Clothing and Toy Sale, Croton-on-Hudson 9 a.m. - 3 p.m.Hemlock Hill Farm Harvest Fest, Cortlandt 11 a.m. - 5 p.m.Cortlandt Family Fun Day 2 p.m. - 7 pm.Fall Festival Westchester Church, White Plains
October 14 - 15: Fall Family Fest Rye Town Park 12 - 5 p.m.October 15Celebrate Dia De Los Muertos at CaramoorBedford Hills Fire Department Open House 1 p.m. - 5 p.m.Sleepy Hollow Street Fair, Beekman Avenue, 10 a.m. - 4 p.m. RESCHEDULED from 10/14
- October 19 - 22, 26 - 29: Lyndhurst After Dark, Tarrytown
October 21 - 22- Museum Village No Scare Halloween, Monroe 11 a.m. - 4 p.m.
- Sheep and Wool Festival, Rhinebeck
- Walktoberfest Farmers and Makers Market
October 21- Westchester & Lower Hudson Valley Light The Night at Playland Park in Rye
- Lewisboro Town Park Oktoberfest 2 - 7 p.m.
- Yorktown Lions Club and Parks and Recreation's Halloween Parade and Carnival, 2 p.m. - 4 p.m. (Moved to October 28th)
- Trunk or Treat Halloween Parade, YMCA Central Westchester at Holy Name of Jesus, Valhalla 12 p.m.
October 22- YMCA of Northern Westchester Halloween Parade, Somers Reis Park, 2:30 p.m.
- Village of Mamaroneck's Spooktacular at Harbor Island Park 11:30 - 2:30
- Sleepy Hollow SUP Witches Festival
- Briarcliff Nursery School Fall Festival, Free Admission Goats, Crafts, Play and more
October 22 - 23: Westchester Craft Crawl- October 27: Bring Your Own Pumpkin Education through Art Event, $36 Briarcliff Nursery School, all ages
- October 28
- Ossining's Spooktacular Fall Fest, Ryder Town Park 12 p.m. - 5 p.m.
- Croton-on-Hudson Goblin Wall 11:45 a.m.
- Trunk-or-Treat at Pelham Funeral Home 3 - 4 p.m.
- Yorktown Lions Club and Parks and Recreation's Halloween Parade and Carnival, 2 p.m. - 4 p.m. (Moved to October 28th)
- Cortlandt Fall Family Fun Day, Festivities begin at 1:30 p.m.
October 29: India Center of Westchester Diwali Mela, Hawthorne 11 a.m. - 4 p.m.
November
- November 4: 34th Annual Festival of Crafts, Whisconier Middle School, Brookfield, CT 9 a.m. -
- November 5: Mama and Child Wellness Expo: Due, New, and YOU! Mount Kisco
- November 5: Yorktown Lantern Walk
- November 11: Mount Pleasant Parks and Recreation Scarecrow Festival - Pre-registration required
- November 18: Harvest Festival Sensory Art ant Play by Macaroni KID with Briarcliff Recreation Department - pre-registration required
- November 18: Holiday Craft Fair, Yorktown
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