7 Must-Do Events in Westchester County Throughout the Year

From antiques, art, and flowers to our own Wine & Food Festival, here are some of the hottest things to do in Westchester County.

Check with event sponsors and/or venues directly for the most up-to-date information.

– April & October –

HV Restaurant Week
Photo by Michelle Carroll

Hudson Valley Restaurant Week

Become a seasoned foodie in just two weeks at this can’t-miss spring/fall biannual event. Serving more than 250,000 dinners, it is the largest and most successful dining event in the region, with more than 200 participating restaurants. Treat yourself and the family to irresistible deals on three-course prix-fixe meals as you eat your way through the region. valleytable.com/restaurant-week

– June –

Westchester Wine & Food Festival
Photo by ©Larufoto/ Luis Ruiz

Westchester Magazine’s Wine & Food Festival

After more than a decade of success, this 21-and-over event remains one of the most anticipated culinary occasions of the year. Travel to multiple locations throughout the area for a celebration of more than 100 top edibles, wines, and spirits. Enjoy Burger & Beer Blast, Grand Tasting Village, and Party on the Pier, among others. westchestermagazine.com/wine-and-food

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– July –

Pleasantville Music Festival
Photo by Lynda Shenkman

Pleasantville Music Festival

This world-class backyard bash brings together national and local music acts, myriad food vendors, a beer-and-wine garden, and a great (zero-waste) vibe. pleasantvillemusicfestival.com

Best of Westchester Party
Photo by Ed Shin

Westchester Magazine’s Best of Westchester Party

Join upwards of 3,000 attendees at the majestic Glen Island Harbour Club for the county party of the year. The annual Best of Westchester celebration brings together industry-leading exhibitors, top-shelf food, drinks and services, illustrious guests, wall-to-wall media attention, and more to celebrate the BEST the county has to offer. westchestermagazine.com/best-of-westchester-party

– September-November –

The Spirits of Sleepy Hollow Country
Photo by Jenna Murray

The Spirits of Sleepy Hollow Country: A Night of Legendary Magic

Long known as a spooky season destination, Sleepy Hollow is living up to its reputation with a new event at Philipsburg Manor. The Spirits of Sleepy Hollow Country: A Night of Legendary Magic features professional magicians Mark Clearview and Nick Wallace, who take visitors on a supernatural journey to conjure the spirits of Sleepy Hollow lore. Join Hulda, Major Andre, and the Headless Horseman for a night of mystery and fun. hudsonvalley.org/events/the-spirits-of-sleepy-hollow-country/

– October –

Lyndhurst
Photo by Clifford Pickett Photography

Lyndhurst After Dark

Experience Gilded Age grandeur while exploring Victorian lore. Timed entry into the mansion allows visitors to walk through and soak up the spirit of the season on a semi-guided tour exploring the darker side of history through the lens of those who have inhabited the property. Visitors get a chance to experience the architecture, decor, and collection items on display while listening to the talented staff regale them about the traditions of the past. lyndhurst.org/events.

– December –

Frosty Day
Photo courtesy of Armonk Frosty Day

Frosty Day

Looking for some holiday fun for the whole family? This free event on Main Street in Armonk is one of the county’s most jolly holiday traditions. Get a firsthand glimpse of seasonal splendor with numerous activities and family events. Enjoy a series of live performances, face painting, hot cocoa and cookies, pictures with Santa, and a grand parade featuring Frosty himself. armonkfrosty.com

- Partner Content -

Our Westchester Home Design Awards event is June 26!

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

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