Passionate About the Westchester County Area
and the Moms Who Live Here

Westchester County Moms Blog Guide to Fall Festivals, Fairs, and Events

It’s pumpkin spice season, and that means that at this time of the year, Westchester County is full of fun weekend events. Here’s the Westchester County Moms Blog guide to fall festivals, harvest fairs, and great autumn events.



September 23

Bronxville Fall Sidewalk Sale10am-5pm (Friday and Saturday)

What to Expect: great bargains and sales throughout the village, free parking in Garden/Kraft Ave lots and Avalon lot.


New Rochelle Art Fest (runs until the 25th), 515 North Avenue, New Rochelle, NY, 10801

What to Expect: art exhibits, open studios, live music and dance, crafts , food, LEGOs, and a classic car show.


September 24

55th Annual Armonk Outdoor Art Show, 10am-5pm (Saturday and Sunday), 205 Business Park Drive, Armonk, NY, 10504

What to Expect: oils/acrylics/watercolors, mixed media, printmaking/drawing/pastels, sculpture, photography/digital art, wearable art,  fine crafts, kids’  activities, personal shoppers, a diverse food court, and free parking. Admission is $12 for 18+, or $10 with coupon.


Chappaqua Children’s Book Festival, 10am-4pm, Bell Middle School, 50 Senter Street, Chappaqua, NY, 10514

What to Expect: more than 90 popular children’s authors, who will have readings and book signings, food, family activities, entertainment, and lots of books.


Fall Harvest Festival at Green Chimneys, 10am-4pm, 400 Doansburg Road, Brewster, NY 10509

What to Expect: pumpkin decorating, hay ride, pony ride, hay maze (for littles), arts &crafts, glitter tattoos, wildlife presentations, trick rope  and lasso demonstration, vendors, crafts, food trucks, scarecrow making ($12). There’s also a children’s fun run and obstacle course (tickets are $6 for adults, $12 for children, $17 for children with fun run.)


Fall Festival at Fieldhome, 10am-4pm, 2300 Catherine Street, Cortlandt Manor, NY 10567

What to Expect: live entertainment, car show, arts & crafts, bake sale, pony rides, raffles, food, and a fall plants sale.


Grape Stomping Festival with Robibero Family Vineyards, 11am-6pm (Saturday and Sunday), 714 Albany Post Road, New Paltz, NY

What to Expect: grape stomping, wine tasting, and food. Tickets are $15 in advance and $20 at the door, but the event is expected to sell out.


Harbor Island International Beer Festival, 1pm-5pm, Harbor Island Park, Mamaroneck Avenue and Boston Post Road, Mamaroneck, NY

What to Expect: almost 200 renowned breweries from around the world, top chefs and food, music, entertainment, and views of the harbor and Long Island Sound. Tickets are $65, and can be purchased here.


Hudson Valley Irish Fest, 11am-7pm, Peekskill Riverfront Green Park, Peekskill, NY, 10566

What to Expect: bands, vendors, exhibits, food, and a children’s area with crafts, face painting, toys, and games. For tickets, click here.


Larchmont 125th Anniversary Celebration, noon-4pm, Larchmont Avenue between Boston Post Road and Cherry Avenue, Larchmont, NY, 10538

What to Expect: contests, games, food trucks, live performances, and big trucks. Free event and open to the public.


Lewisboro Library Fair, 10am-4pm, Onatru Farm Town Park, 104 Elmwood Road, South Salem, NY, 10590

What to Expect: book sale, toy sale, silent auction, food, vintage cars, maze, vendors, music, and kids’ games. Admission is free for Lewisboro residents and $20 for non-residents.


Maryknoll Fathers and Brothers Car Cruise and Drive-In, 4pm-10pm, Maryknoll Mission Center, 55 Ryder Road, Ossining, NY, 10562

What to Expect: classic cars and an outdoor showing of American Graffiti. There is reserved parking for classic cars, and limited parking for contemporary cars.


Ninjago Weekend at LEGOLAND, 10am-9:30pm (Saturday) and 10am-7:30pm (Sunday), 1 Ridge Hill Boulevard, Yonkers, NY, 10710

What to Expect: All of LEGOLAND’s regular attractions, plus a special scavenger hunt and more. To guarantee admission, buy tickets in advance.


Wartburg’s Fall Festival, 11am-5pm, 1 Wartburg Place, Mount Vernon, NY, 10552

What to Expect: Children’s area, food, bouncy castle, vendors, live entertainment, and a farmers’ market.


September 25

Muscoot Farm Make Your Own Halloween Decorations, 1pm-3pm,  51 Route 100, Katonah, NY, 10536

What to Expect: In addition to the farmers’ market at Muscoot Farm, there will also be a station to make and take your own Halloween decorations.


Touch a Truck in Cortlandt Manor, 10am-4pm, 155 Highland Avenue, Verplanck, NY, 10596

What to Expect: firetrucks, ambulances, police cars, farm equipment, construction trucks, face painting, food, and balloon art. Admission is $5 per person and there’s a horn free hour between 10-11.


Westchester County Car Show, 11am-5pm, Glen Island Park, New Rochelle, NY, 10805

What to Expect: a wide variety of classic and collectible vehicles, motorcycles and street rods. Admission is free, but parking is $5 per car.


White Plains Jazz & Food Festival, 12pm-5pm, Mamaroneck Avenue, between Martine and Mitchell, White Plains, NY, 10601,

What to Expect: enjoy five sets of music and a variety of international foods. Admission is free.


September 28

Fall Carnival- Sts. Peter& Paul- St. Ursula Church, 4pm-10pm (Wednesday and Thursday), 4pm-11pm (Friday), 11am-11pm (Saturday), and 2pm-10pm (Sunday), 129 Birch Street, Mount Vernon, NY, 10552

What to Expect: rides, carnival, games, food, and vendors.


September 29

Westchester County Be Green Kids Consignment Fall 2016 Sale, 6pm-9pm (Thursday, New & Due VIP- must register), 9am-7pm (Friday, open to the public), and 9am-1pm (Saturday, discount day) SUNY Purchase Athletic Facility, 735 Anderson Hill Road, Purchase, NY, 10577

What to Expect: consignment children’s clothing, sporting equipment, baby and toddler equipment, toys, and brand new puzzles, stuffed animals, arts & crafts supplies, DVDs, and books.


October 1

Harvest Fest at Stone Barns, 10am-3pm, 630 Bedford Road, Pocantico Hills, NY, 10591

What to Expect: Festivities for the whole family include hands-on farming and food activities, live music, a seasonal farm and food market with delicious fare, hayrides, a turkey parade and more. Individual tickets are sold out, but packages are still available here.


Neuburger Museum of Art Fall Family Day, 1pm-4pm, SUNY Purchase, 735 Anderson Hill Road, Purchase, NY, 10577

What to Expect: artists will guide visitors through experimentation with media and techniques inspired by current exhibits. Cost is $10 per child.


October 7

Eastchester Columbus Day, 7pm-11pm(Friday), 1pm-11pm (Saturday), 1pm-11pm (Sunday), 1pm-6pm (Monday), Lake Isle County Club, 660 White Plains Road, Eastchester, NY, 10709

What to Expect: carnival, homemade meatball contest, homemade wine contest, DJ, live entertainment, parade (Sunday at 3:30pm), and fireworks (Sunday at 9pm).


Fall Festival “Heroes For A Cure”, 6pm-10pm (Friday), 1pm-10pm (Saturday) 1pm-8pm (Sunday), 1pm-8pm (Monday), Rosmarins Day Camp , 12 School Road, Monroe, NY 10950

What to Expect: games, carnival rides, food, entertainment, live music, vendors, local brews and wines, local celebrities, and hot air balloon rides. Benefits Make a Wish Hudson Valley.


October 8

Community Day at the Dia:Beacon, 11am-6pm, Dia:Beacon, 3 Beekman Street, Beacon, NY

What to Expect:Residents of counties Columbia, Dutchess, Greene, Orange, Putnam, Rockland, Sullivan, Ulster, and Westchester are invited to Dia:Beacon on Community Free Days free of charge.


Touch a Truck, 10am-2pm, 53 Winter Hill Road, Tuckahoe, NY, 10707

What to Expect: trucks, construction vehicles, a helicopter, ambulance, and fire truck, plus food vendors and family activities. Cost is $8 in advance or $10 at the door. You can buy tickets here.


Peekskill Rotary Horse Show, 9am-5pm (Saturday,) and 8am-5pm (Sunday), Blue Mountain Reservation, 435 Welcher Avenue, Peekskill, NY, 10566

What to Expect: riding show featuring English and Western riding classes, pony rides, hay rides, country fair and craft market, bouncy castle and slide, home baked goods, apples, pumpkins, mums, and a food tent. Admission and parking are free, but there are fees for the other activities.


Sugar Loaf Fall Festival, 10am-6pm (Friday-Sunday), 1371 Kings Hwy, Chester, New York 10918

What to Expect: arts & crafts vendors, food vendors, and live music all day.


October 9


Family Bonfire Night at Boscobel,6pm-9pm, 1601 Route 9D, Garrison, NY, 10524

What to Expect: a giant bonfire, live music, marshmallows and toasting sticks, stargazing, and glow sticks, food and drinks available for purchase. Tickets are $15 per adult and $3 for children 2-10.


Hastings Flea, 10am-4pm, Hastings Train Station Parking Lot

What to Expect: antique and vintage furniture, jewelry, crafts, collectibles, comics, posters, music, and food.


October 14

Holbrook Cottage Harvest Fest, 10am-5pm (costume collection 10am-2pm), 1253 Pleasantville Road, Briarcliff Manor, NY, 10510

What to Expect: shopping, crafts, story time for kids, donut making, and a collection for Halloween costumes to benefit Ossining Children’s Center.


Oktoberfest at Exit 4, 5:30pm-11pm(October 14-15), Exit 4 Food Hall, 153 Main Street, Mount Kisco, NY

What to Expect: beer, contests, giveaways, food, music, and more. Free admission, children welcome.


October 15

20th Annual Sleepy Hollow Street Fair, 10am-5pm, Beekman Avenue, Sleepy Hollow, NY

What to Expect: kids’ carnival, vendors, and food. Free admission.


Hudson Valley Crafted, 9am-5pm, Dutchess Stadium, 1500 Rt. 9D, Wappingers Falls, NY, 12590

What to Expect: apparel, jewelry, home goods and decor, art, gourmet food, and lots of other great stuff, plus food vendors. Parking is free, and there will be a free shuttle bus from the Beacon Metro North station to Dutchess Stadium. Admission is $8 in advance or $10 at the door (cash only).


October 16

Fall Festival at Greenburgh Nature Center, 11am-3pm, 99 Dromore Rd, Scarsdale, NY 10583

What to Expect: fall activities including including scarecrow building, pumpkin carving and painting, cider making, scavenger hunts, tractor rides, and more. Tickets are $5 for members, $10 for non-members who preregister, and $8 for members and $15 for non-members the day of. Tickets are available here.


Sheldrake’s Fall Festival, 1pm-4pm, 685 Weaver Street, Larchmont, NY, 10538

What to Expect: doggie costume contest, learn to build a bug house or a fairy house, music, face painting, bake sale, Story Walk, and more.



Bear Mountain Oktoberfest, 12pm-6pm, every Saturday and Sunday, through October 30. Bear Mountain State Park, Bear Mountain, NY

What to Expect: tons of beer and food, live music and entertainment every day, vendors, and fall foliage. Parking is $10 per car, but admission is free, and you can also enjoy the Bear Mountain grounds. There is a playground and carousel for small children.


Did we miss your favorite fall festival, fair, or event? Let us know- [email protected]




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