With the start of school less than two weeks away, it’s time to start planning ahead for some outdoor fall fun. Break out your comfy sweater and order your favorite pumpkin spice drink and plan a day to take in fall foliage, visit a farm or brewery or head to the infamous Sleepy Hollow and Tarrytown. Here are some of our favorite things to do in Westchester County. Trust us, it will be worth the trip.

Please note that many of these locations are able to accommodate social distancing but policies may change throughout the season. Call or check online before visiting.

Harvest Moon Farm and Orchard image courtesy Historic Hudson Valley 

Pick Your Own and Farm Adventures

Westchester County is home to dozens of farms with different specialties and lots of them offer favorite fall activities like apple picking, hay rides and harvest festivals. The Westchester Farm Trail connects 13 farms across 17 miles, stretching all the way into North Salem. Stop by Alfred B. DelBello Muscoot Farm to meet farm animals, take on farm chores and learn how to make maple syrup. Harvest Moon Farm and Orchard is popular for apple picking and The Meadows Farm is the perfect spot for pumpkin picking. Many of the farms are also family-owned and rich with history—with some being as old as 300 years.  

Breweries, Cideries, Distilleries and Wineries

In recent years, Westchester has become a popular destination for craft beer lovers. With 16 breweries and distilleries to visit, plus a cidery and micro-winery, there’s a lot to choose from. These spots offer drinks brewed on-site that you can enjoy on a crisp autumn day. Here are a few spots to try. 

Decadent Ales


Try the zany flavors of Decadent Ales, which is currently offering online ordering. Unique flavors include Toasted Marshmallow Pale Ale, Banana Macadamia Fudge Cake Draft and French Toast Stout. The food menu is full of classics like tacos, burgers, chicken sandwiches and even a few seafood options. 


Hardscrabble Cider

North Salem

Westchester’s cidery is located right on Harvest Moon Farm and Orchard and specializes in farm-to-table drinks. First launched in 2015, Hardscrabble Cider features a range of drinks on tap with flavors like White Peach and “Black Dirt” Beet. They also have some delicious looking pizzas, burgers and donuts to enjoy with your drink. 


River Outpost Brewing


Located on the shore of Lents Cove on the Hudson River, this brewery features nine original beers ranging from IPAs to stouts that are all brewed on site. There’s plenty of outdoor seating, so you can stay socially distant while enjoying your meal and the fall scenery. The food menu is full of delectable choices including specialties like lobster carbonara, lemon oregano grilled calamari and smoked beef brisket. 


South Salem Winery

South Salem

This micro-winery boasts being the first in the Hudson Valley. The grapes are mostly sourced from a Long Island vineyard although some come from as far as California. The wines are crafted in small batches, with as few as 300 bottles, and are unfiltered, unpasteurized and contain only naturally-occurring sulfides.  Located in the midst of Gossett Bros. Nursery, the scenery is sure to be great, too.


Foliage Viewing and Outdoor Adventures

One of the most quintessentially fall things to do in Westchester is to take in the gorgeous fall foliage. The county is home to 24,000 acres of parkland which are part of the larger 50,000 acres of open space. It’s the perfect place for a light walk, hike or even a mountain bike ride.


There are five major pathways and greenways sprawled throughout Westchester and they’re all sure to provide great views of the changing leaves. The paved Bronx River Pathway travels through the Bronx River Reservation and is perfect for a relaxing stroll. The Colonial Greenway will take you back in time as you trek part, or even all, of this 15-mile loop that travels through neighborhoods where famous American figures, like Thomas Paine, once lived. The North-South County Trailway is 36.2 miles long and is great for biking. Notable stops along it include Kitchawan Preserve and Tibbetts Brook Park. Also check out the Briarcliff-Peekskill Trailway and the Old Croton Aqueduct State Historical Trail.


Helicopter Tours

What better way to fully take in the beauty of the Hudson Valley than from above—in a fall foliage helicopter tour. Wings Air will give you a birds-eye view filled with unforgettable scenes as you soar above Westchester and the Hudson Valley. Helicopters take-off from both Westchester and Manhattan. Pilots also serve as tour guides who will point out landmarks and historic sights along the way. Tours can typically be booked between September 15 and November 15 but these dates may change as the leaves do.  


Halloween Fun and Frights

When the sun goes down, it starts to get spooky in Westchester County especially when Halloween is near. Get into the Halloween spirit with these fun, and perhaps a tiny bit frightening, activities.

Explore Sleepy Hollow and Tarrytown

Venture into the village that inspired Washington Irving to write The Legend of Sleepy Hollow, famous for characters like the Headless Horseman, over 200 years ago. Throughout the fall, you’ll be able to catch spooky attractions like haunted hayrides, tours of the 300-year-old Philipsburg Manor and Old Dutch Church, dramatic live performances of The Legend and so much more

Historic Hudson Valley

The Great Jack ‘O Lantern Blaze

Looking for some inspo for this year’s doorstep jack ‘o lantern? From September through November you can check out this jack ‘o lantern display which will definitely blow you away (and give you a few ideas for your own carvings along the way). See a display of over 7,000 hand-carved pumpkins arranged to create things like a 25-foot tall Statue of Liberty, zodiac signs and a firetruck (a new addition this year). Some even move, like the Pumpkin Carousel and Pumpkin Windmill. There’s even a synchronized light show. The display is spread throughout the historic Van Cortlandt Manor and is open daily between September 18 and October 31 with limited dates in November. This year’s display will allow for social distancing and advanced tickets are required.

Sleepy Hollow Cemetery Lantern Tour

Tour Sleepy Hollow Cemetery

Sleepy Hollow Cemetery is the final resting place of famous figures like Andrew Carnagie, William Rockefeller and three of Alexander Hamilton’s children, Eliza, Angelica and James. Washington Irving, who brought the town fame, is also buried there. The cemetery was first founded in 1849, covers 90 acres and is home to over 45,000 interments. Daytime tours are great for families but there are also night tours for those with spookier tastes. The classic tour will teach you about the famous people buried there and also has a nighttime version guided by lantern light. Another night tour will introduce you to the dark and true stories of Sleepy Hollow (this one’s for ages 18+ only). Look out for special events throughout the month of October like literary readings featuring the works of Edgar Allan Poe and Washington Irving, Champagne Cocktails with the Dead (ages 21+ only) and Spooky Stories for kids.