The Top 21 Annual Events In Briarcliff Manor

Briarcliff Manor is home to dozens of annual events, from arts and music festivals to spooky Sleepy Hollow traditions in the autumn. Residents and visitors enjoy Westchester County’s rich culture and history, and the Briarcliff Manor community is a vibrant and family-friendly destination all year round.

Here is a list of 21 annual events around Briarcliff Manor, organized by month.


1. Winter Extravaganza Baseball Card Show

Baseball card collectors and enthusiasts gather from miles around for the Winter Extravaganza Baseball Card Show at the Westchester County Center in White Plains. This all-day January event features thousands of autographed cards, vintage baseball cards, modern baseball cards, and more. The Winter Extravaganza Baseball Card Show is a collector’s dream!

2. The Great Westchester Train and Toy Show

The Great Westchester Train and Toy Show is the biggest toy show in the Northeast and features hundreds of vendor tables. At this train and toy show, you’ll see antique toy trains, new toys, every gauge of toy train, toy train parts and accessories, and more.

You can also expect appraisals, rare and vintage books, test tracks, games, and a huge variety of collectibles.


3. Teatown Hudson River EagleFest

For Briarcliff Manor’s birders, naturalists, and eagle appreciators of all walks of life, the Teatown Hudson River EagleFest is a must-see event. This celebration of the American bald eagle’s homecoming to the Lower Hudson Valley is attended by thousands. This event is held at Teatown, a thousand-acre nature preserve in Westchester, and is the home of hundreds of New England wildflowers, science day camps, and stunning locations for bird sightings.


4. Spring Westchester County Home Show

The Spring Westchester County Home Show is the biggest home show in Westchester County. This event features some of the most opulent enclaves in the greater Hudson Valley area and an eclectic selection of home products and services. Among the exhibitors at the Spring Westchester County Home Show are home builders, general contractors, mosaic tile experts, lighting experts, modern home designers, and more.

5. St. Patrick’s Day Parades

For those looking for a spirited time in the spring, Briarcliff Manor and Westchester County are home to several St. Patrick’s Day Parades from White Plains to Tarrytown and Sleepy Hollow. Experience a celebration of St. Patrick like you’ve never seen, in historic Westchester County. Just don’t forget to wear green!

6. Hudson Valley Restaurant Week

For lovers of chef-prepared cuisine, fine wine, and exquisite dining ambiance, Hudson Valley Restaurant Week is an annual delight. Feast on seasonal, three-course meals, made with farm-to-table ingredients, paired with craft beers, distinguished wine, and mouth-watering desserts. To enjoy the dozens of participating Westchester restaurants, make your reservation today!


7. Colonial Day

For a family-friendly experience of New England’s colonial history, visit New Rochelle’s Colonial Day. Witness authentic costumes, smithing, coopers, music, and a historical one-room schoolhouse. Colonial Day is enjoyable for all ages, and provides a glimpse into a day in the life of Westchester County’s vivid history.


8. Crafts at Lyndhurst

Crafts at Lyndhurst features the best in craft and artwork, with 300 independent craftspeople.  Authentic handmade pieces make perfect gifts for weddings, graduations, birthdays, and more. Lose yourself in an exciting array of handmade goods, including drawings, photography, painting, ethical jewelry, and woodwork. With face painting, puppet theater, and a crafts workshop, Crafts at Lyndhurst is a delightful destination for the whole family.


9. Westchester Magazine’s Wine & Food Festival

For foodies, restaurant tourists, and dining enthusiasts, Westchester Magazine’s Wine & Food Festival is an annual favorite. Experience seven distinct dining events over the course of seven days, featuring beer, spirits, wine, world-class food, and the best chefs in Westchester.  This popular event reflects the rich culture of Westchester County and celebrates local farmers and restaurants.

10. Bicycle Sundays on the Bronx River Parkway

Since 1974, Bicycle Sundays have been a staple of Westchester County. Tens of thousands of participants traverse the half marathon loop through Westchester County on bicycles or on foot. Bicycle Sundays are brought to you by the Westchester Parks Foundation and sustains itself without any public funding. Join the fun, in the name of environmental conservation and personal fitness!


11. Caramoor Summer Music Festival

The Caramour Center for Music and the Arts is a cultural hub for exemplary music and arts, and has hosted an annual music festival since 1945. Opera aficionados and music appreciators of all experience levels delight in the bel canto repertoire, with performances of Rossini’s Otello and Donizetti’s Elisabetta, among other operatic works. Experience a true Westchester tradition!


12. Moon Viewing Concert

Since 1966, the Moon Viewing Concert has dazzled audiences with sights, sounds, and tastes. The Japanese Stroll Garden will be illuminated with paper lanterns, with a Japanese Tea Ceremony, a Bento dinner, and traditional Japanese music performance. This tradition is a celebration of harmony, respect, purity, and tranquility.


13. Yorktown Grange Fair

The Yorktown Grange Fair is an annual fair that celebrates hometown values, and the historic roots of Westchester County. This lively event takes place on the Grange Fairgrounds, and features live music, livestock, games, contests, rides, and other exciting events. The Yorktown Grange Fair welcomes all ages and has fun amenities for the whole family.

14. Jazzfest

Jazz is a uniquely American form of music, and Westchester’s annual Jazzfest is sure to delight music lovers of all ages. This five-day event features Pablo Mayor, Alexis Cole, Emedin and Tropical Turbulence, Gil Parris, Veronica Swift, and many more acclaimed jazz and improvisation artists. Jazzfest is a staple of Westchester’s thriving music scene and attracts jazz enthusiasts from miles around.


15. The Great Jack O’Lantern Blaze

One of Westchester’s most awe-inspiring events is The Great Jack O’Lantern Blaze, in which thousands of hand-carved jack o’ lanterns are lit, and arranged across the historic landscape. Witness the gorgeous Van Cortlandt Manor decorated from September through November, and all proceeds from the Blaze support the Historic Hudson Valley, a non-profit education organization.

16. Tarrytown Halloween Parade:

There is no shortage of frightening fun near Briarcliff Manor in the autumn. Since 2002, the Tarrytown Halloween Parade has delighted spectators with dozens of spooky parade floats, musical groups, merchants, and a sea of outrageous costumes. The parade has grown in size every year and has quickly become a Tarrytown staple.


17. Annual Valenti Thanksgiving Day Parade

For 55 years, the annual Valenti Thanksgiving Day Parade has delighted thousands from the Huguenot Children’s Library to Maple Avenue. Experience the floats, marching bands, and the lively parade atmosphere of New Rochelle. Make sure you don’t forget the annual pancake breakfast at New Rochelle High School before the parade!

18. Christmas Tree and Menorah Lightings for Holidays in Westchester

For a festive holiday season, there’s no beating the Christmas Tree and Menorah Lightings. Westchester features plenty of holiday events across several cities, including tree lightings in Yorktown, Irvington, Tarrytown, and Chappaqua. Menorah lightings can be witnessed in Bedford, Armonk, Tuckahoe, and Irvington.

19. Frosty Day

Armonk celebrates the annual homecoming of Frosty the Snowman, who calls Armonk his home. The Frosty Day parade is free to the public, and features plenty of music, floats, dancing, and costumes, all through the Historic District of Armonk, and is guaranteed to be winter fun for the whole family.


20. Westchester’s Winter Wonderland

If you’re looking for affordable fun for the whole family, Westchester’s Winter Wonderland is the natural choice. From the Winter Wonderland Holiday Circus to the FUNderland Village and a lively light show, Winter Wonderland has no shortage of festive fun.

21. New Years Eve Celebration and Ball Drop

The greater Briarcliff Manor area has several options for New Years celebrations, including White Plains, Peekskill, and the Palisades Center across the Hudson in West Nyack. Experience the traditional New Years ball drop at Kensico Dam in Valhalla or White Plains. Additionally, there will be plenty of parties, dinners, and champagne around Westchester.

More events around Briarcliff Manor:

There is no shortage of annual events near Briarcliff Manor and the surrounding Westchester County. This historical society takes pride in its lively culture, distinctive landscape, and exquisite legacy. To learn more about the vibrant and historic community around Briarcliff Manor, get in touch with The Club at Briarcliff Manor today!

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