Embrace Westchester

Fall 2023 Event Guide

Westchester County New York

_{Brought to you by: The Sherry Wiggs Team at Houlihan Lawrence}

_{Get out your flannels and sweaters, fall is finally around the corner! Sherry Wiggs is your Local Guide for all things Fall 2023. Below you will find a list of festivals and events, apple orchards, pumpkin patches, food and farmer’s markets, walking trails & more!}

September

Select Dates in September & October: Bear Mountain Oktoberfest at Anthony Wayne Recreation Area; Bear Mountain, NY

September 1 -3: Hot Air Balloon Festival; Tymor Park, Union Vale.
Family activities, amusement rides, games, live music, a grand light show of hot-air balloons illuminating the night sky, patriotic music and a fireworks display eclipsing behind the lit balloons. For more: https://www.dcrcoc.org/balloonfesthv.org

September 1- 4: Barton Orchards Sunflower Festival; Poughquag, NY For more information: https://www.bartonorchards.com/events-calendar/

September 6th – 10th: White Plains Jazz Festival; White Plains, NY Some shows are free and some require the purchase of tickets. Full schedule and link to purchase tickets can be found here.

September 8th: Food Truck Friday; Pascone Park – Ardsley, NY For more information: https://www.ardsleyvillage.com/home/news/food-truck-friday-festival-sept-8th

September 8th – 10th: Mt. Kisco’s Septemberfest; Mt. Kisco, NY – carnival & street fair. For more information, click here.

September 8th – 10th: Fall Crafts at Lyndhurst; Tarrytown, NY Tickets required. Fall Crafts at Lyndhurst is a massive market featuring local vendors, gourmet foods and craft shows. Details, hours and purchase of tickets available here.

Starting September 9 – Select Saturdays in September & October: Harvest Moon Fall Festival
In addition to family-favorite farm activities, such as hayrides and pony rides, attendees can pick their own apples and pumpkins on-site. For more: Harvestmoonfarmandorchard.com

September 9th & 10th: Hudson Valley Food & Wine Festival at the Dutchess County Fairgrounds; Rhinebeck, NY — Tickets required for this event. For schedule, event details and tickets, click here.

Sunday September 10th: Armonk Cider & Donut Festival & Fall Carnival; Wampus Brook Park – Armonk

September 13th – 17th: San Gennaro Festival; Yorktown Heights, NY Hours, Event Schedule and details can be found here.

September 14 – 17: Greek Festival; Holy Trinity Orthodox Church in New Rochelle, NY

September 16th at 4PM: JP Doyles Block Party; Tarrytown, NY – Hang out and Enjoy the music for free, or join the VIP bash by purchasing tickets here.

September 17 from 12PM – 5PM: Peekskill Brewery Oktoberfest; Peekskill, NY. For more information, Click here.

September 23rd from 11AM – 7PM: Hudson Valley Irish Festival on the Peekskill Riverfront; Peekskill, NY — A very popular event, multiple years running. Tickets and additional information can be found here.

September 23: Pleasantville Block Party; Pleasantville, NY Free admission. Car Show, Kids Fun Zone & More!

September 30th from 1PM – 5PM: Oktoberfest; Kingsland Point Park – Sleepy Hollow, NY Open to all ages.

September 30th at 2PM: Irvington’s Rocktoberfest: Mattheisen Park; Irvington, NY – Food trucks, music and fireworks. All ages welcome. Tickets available upon entry.

September 30th from 10AM – 4PM: Chappaqua Children’s Book Festival; Chappaqua NY — This is a free event and great for children of all ages. For details and location, click here.

September 30 & October 1st: Hudson Valley Garlic Festival; Saugerties, NY This massive festival hosts hundreds of local vendors. Tickets required. Event details, location, tickets and schedule can be found here.

October

October 1 from 9 AM – 5PM: Warwick Apple Fest; Warwick, NY – 75+ Vendors. For more information, click here.

October 1 from 1PM – 6PM: Mount Pleasant Street Fair – More information to come, click here for details.

October 7th at 1PM Ferry Festa; Dobbs Ferry, NY See event schedule here.

October 7th at 12PM: Croton Oktoberfest; Grand Street Croton-on-Hudson, NY Additional Details can be found here.

October 7: Pound Ridge Harvest Festival; Pound Ridge, NY – For more information, click here.

October 8: White Plains Oktoberfest; White Plains, NY

October 14th: Sleepy Hollow Street Fair; Sleepy Hollow, NY For Updates and location, click here.

October 15th: Sup Witches Paddle Board Costume Event; Sleepy Hollow, NY – Click here for more!

Saturday October 21st from 5PM – 11PM: Sleepy Hollow Block Party; Sleepy Hollow, NY — This is a free event. Additional event details and location can be found here.

Saturday October 28th at 5:30PM: Tarrytown Halloween Parade; Tarrytown, NY For location and additional details, click here.

For Families with Young Children…

There are Plenty of things to do with young children around the Rivertowns during the fall months. On Select dates, starting September 28, The Bronx Zoo will be hosting Pumpkin Nights, an illumination of over 5,000 pumpkins. The zoo will also continue their Boo at the Zoo experience which will be held Saturdays & Sundays starting September featuring costume parades, crafts and more.

Bear Mountain will be hosting its own version of Boo at the Zoo on October 28 from 10:30AM – 3PM at the Trailside Museum and Zoo location in Highland Falls.

FEATURED: For those of you that might be looking for something a little bit closer to home, The Greenburgh Nature Center‘s Family Movie Night will be going on during select dates in September and October.

Greenburgh Nature Center will also be hosting “Run Wild” forest runs and obstacle courses for children ages 5 – 15 years September 30 & October 1st. A full calendar of events for The Greenburgh Nature Center as well as details can be found here. The Center has a lovely playground and activity center for children of all ages on the grounds.

If you’re looking for places to go with the kiddos during down time, the Rivertowns boast a wide variety of parks and playgrounds. A few local favorites include: Mattheisen Park in Irvington, Pierson Park in Tarrytown and Barnhart Park in Sleepy Hollow.

The region also boasts a variety of nature centers and preserves including:

Hammond Museum & Japanese Stroll Garden in North Salem, Untermeyer Park & Gardens in Yonkers, Pruyn Santuary in Chappaqua, Rye Nature Center, Weinberg Nature Center in Scarsdale and The Scenic Hudson Riverwalk Park in Tarrytown.

All of which make lovely outings with plenty to see and explore!

Apple & Pumpkin Picking …

Some local favorites include:

Stuart’s Farm: Granite Springs, NY

Wilkens Fruit & Fir Farm: Yorktown Heights, NY

Harvest Moon Farm & Orchard: North Salem, NY

Fishkill Farms: Fishkill, NY

Spooky Activities & Halloween Happenings…

Visit the Old Dutch Church & Burial Grounds in Sleepy Hollow, NY *Be sure to visit The Sleepy Hollow Cemetery next door to see the wooden bridge that Washinton Irving describes in his book The Legend of Sleepy Hollow.*

Hulda: The Other Legend of Sleepy Hollow Select Saturdays & Sundays in October. Must buy Tickets in Advance. Limited Availability. For tickets and showings, click here.

Visit Historic Hudson Valley‘s Unique Sites View Events, Tours & Buy Tickets here.

Kykuit – The Rockefeller Estate; Sleepy Hollow, NY

Philipsburgh Manor; Sleepy Hollow, NY

Washington Irving’s Sunnyside; Irvington, NY

Union Church of Pocantico Hills

Van Cortlandtmanor; Croton-on-Hudson, NY

HHV’s “Great Jack O’Lantern Blaze”at Van Cortlandt Manor in Croton-on-Hudson, NY. For Tickets and Schedule, click here.

HHV’s “Irving’s Legend” at Washington Irving’s Sunnyside in Irvington, NY. September 30 – October 31. For tickets and schedule, click here.

Visit Irvington’s Infamous Octagon House The only fully domed Octagonal residence known in existence. Tours available throughout September and October. For scheduling and tickets, click here.

Visit Lyndhurst Mansion in Tarrytown, NY View Events, Tours & Buy Tickets here.

Lyndhurst After Dark Candlelight Mansion Tours Select Dates in October
Lyndhurst Spirited Mansion Weekends “At Your Pace” Viewings available Select Saturdays & Sundays in October

Visit the Tarrytown Music Hall in Tarrytown, NY: View Events, Tours & Buy Tickets here.

Ghost Tours of the Tarrytown Music Hall – October dates To be Announced. For Updates and Tickets, click here.

Ride the Sleepy Hollow Haunted Hayride: Sleepy Hollow’s annual event. October 20 & 21 only.

Looking for a Day Trip? Go to The Renaissance Faire in Tuxedo, New York — Saturdays & Sundays through October 8.. For Event Schedule & Tickets, Click here.

Extended Walks & Sightseeing

Local Favorites include:

Croton Gorge Park & Croton Dam in Cortlandt: a 97-acre property at the base of the Croton Dam and affords impressive views of the dam and spillway. The park is a popular spot for fishing, picnicking and hiking, with direct trail access to New York State’s Old Croton Aqueduct.

The Marshlands Conservancy in Rye: a 147-acre wildlife sanctuary composed of diverse habitats. Forest, meadow, salt marsh and shore can be explored and appreciated here. There are three miles of trails and one-half mile of shoreline along the Long Island Sound.

Teatown Lake Reservation in Ossining, NY: A 1,000-acre nature preserve with walking & hiking trails and education center.

Tarrytown Lakes in Tarrytown, NY: a 72-acre scenic escape to walking and biking trails, kayaking in season, birding and, for local residents, fishing.

Boscobel House and Gardens in Garrison, NY: A Beautiful early 19th Century Estate. Located in close proximity to downtown Cold Spring (definitely worth a visit!) Admission required to enter the grounds. For more information, click here.

Farmer’s Markets …

The Hudson Valley Region is rich in fertile soil with an abundance of agriculture. The Rivertowns offer some of the best Farmer’s Markets (literally – The TASH has been ranked nationally) and boasts offerings from fresh produce, meats and dairy, to sangrias, honey, small gifts and more!

Below is a list of local favorites:

The TASH; Patriot’s Park – Tarrytown, NY; Saturdays from 8:30AM – 1:30PM through 11/19

Irvington Farmer’s Market; Main St. – Irvington, NY; Sundays from 9AM – 1:30PM through mid-November.

Pleasantville Farmer’s Market; Memorial Plaza – Pleasantville, NY; Saturdays from 8:30AM – 1PM through 11/19

Chappaqua Farmer’s Market; Chappaqua Train Station, South Lot – Chappaqua, NY; Saturdays from 8:30AM – 1PM through December

Muscoot Farm Farmer’s Market; Muscoot Farm – Katonah, NY* Great to bring the kids to and walk around the farm/visit 50+ animals after! Sundays from 9:30AM – 2:30PM through 11/21.

& If you like Food & Drinks, Try these…

Goosefeather: Tarrytown, NY

Blue Hill at Stone Barns: Tarrytown, NY

Horsefeathers: Tarrytown, NY

Hudson Farmer & The Fish: Sleepy Hollow, NY

Bridgeview Tavern: Sleepy Hollow, NY

Red Hat: Irvington, NY

Sambal: Irvington, NY

MP Taverna: Irvington, NY

The Boathouse: Ossining, NY

Sushi Mikes: Dobbs Ferry, NY

The Cookery: Dobbs Ferry, NY