Bordered by the Hudson River on the west and by Long Island Sound to the east, Westchester County spans across 500 square miles of New York state and is a perfect place for families, couples and solo travelers eager to enjoy the crisp fall weather and celebrate the season. This year, travelers will look to the great outdoors for wide-open spaces where they will feel comfortable and safe to celebrate fall and all the exciting events that come with it.  

Aerial view of the Hudson

To kick off the Autumn season, many travelers take to Westchester County for the famous Halloween celebrations. Starting in September, The Great Jack O’Lantern Blaze fills Van Cortland Manor’s historic grounds with a magnificent display of more than 7,000 illuminated jack o’ lanterns. This year, the event will be organized to promote social distancing efforts, including limiting guest capacity and keeping everything outdoors. 

Over 200 years ago, Westchester native, Washington Irving published the classic novel, “The Legend of Sleepy Hollow” and introduced the world to unforgettable characters like the Headless Horseman, Ichabod Crane and Katarina Van Tassel. These days, the village of Sleepy Hollow welcomes visitors to check out the Old Dutch Church from Irving’s tale and the Sleepy Hollow Cemetery, with famously historic graves, including Washington Irving, Andrew Carnegie, William Rockefeller and Alexander Hamilton’s children, Eliza, Angelica and James. 

Headless Horseman

And what’s a fall trip without apple picking or wagon rides? Farms of all kinds are located in Westchester County, many of these farms are family-owned and operated, some dating back 300 years. Harvest Moon Farm and Orchard in North Salem is open to the public, but by reservation only, while the Fruit & Fir Farm in Yorktown Heights is also open, but at 50% capacity only. Orchard picking, the corn maze, the bakery and the farm market will all be open, but guests are required to wear face masks at all times.  

For next-level leaf peeping, Mianus River Gorge Preserve in Bedford is a trail that looms 40 feet above the Mianus River. Despite the exhilarating view, the hike is easy and perfect for the whole family. And at Croton Gorge Park in Cortlandt, an easy two-mile hike includes gorgeous vistas of the New Croton Dam and its autumnal color palette. Additionally, the County offers a one-of-a-kind leaf peeping opportunity with Wings Air. Guests can score above the Hudson Valley for a bird’s-eye view of Westchester County’s colorful foliage. 

Wilkens Fruit & Pie Farm

In 2020, for the first time ever, the New York City Michelin Guide included restaurants from Westchester County. Many of the recognized eateries, including The Cookery in Dobbs Ferry and Southern Table in Pleasantville offer superb take-out and curbside pickup options, ideal for travelers looking to grab-and-go for a picnic.  

In recent years, Westchester has emerged as a hub for craft beverage enthusiasts in New York state. Some of the best places to sip and savor are at River Outpost Brewing located in Peekskill, Wolf & Warrior in White Plains, Decadent Ales in Mamaroneck Sing Sing Kill in Ossining and Captain Lawrence Brewing Company in Elmsford. Westchester County is also home to a cidery and a micro winery. South Salem Winery produces small batches of hand-crafted wine in the beautiful surroundings of the Gossett Bros. Nursery, while Hardscrabble Cider on Half Moon Farm and Orchard epitomizes handcrafted, farm-to-bottle beverages with the dedication of a family-run business.  

Red bridge in the fall

A former convent turned Westchester’s newest luxury hotel, The Abbey Inn & Spa is a boutique hotel featuring 42 distinctive guest rooms and suites, a full-service spa, and the Apropos farm-to-table restaurant delights with a Mediterranean-inspired menu that celebrates the bounty of the Hudson Valley. Located on historic Fort Hill, where Washington’s army set up a key lookout post in the Revolutionary War, the former 1902 convent of the Episcopal Sisters of Saint Mary’s has been beautifully repurposed as a secular retreat for today’s discerning travelers. Located just one hour from midtown Manhattan, The Abbey Inn feels a world away.  

Biking North County Trailway

Before taking a trip to Westchester, travelers should make a list of the places they would like to visit and ensure those places are open to the public. When possible, make reservations before arriving or plan to visit during less popular times. Also review the sanitation and social distancing protocols. Don’t forget to have a few back up options in case plans change. Most importantly, have a safe and happy time!