Favorite Escapes

Westchester has it all this fall! From apple picking to pumpkin patches, spooky Halloween adventures to family friendly fun, you’ll find your perfect autumnal getaway in Westchester. Choose one of our weekend itineraries below, or try them all. See the colorful foliage, breathe in the crisp air and enjoy all Westchester has to offer during one of our favorite seasons of the year.

Explore all that Westchester County has to offer this season and beyond!
Click here to view our Farms & Orchards Visitor Guide.

Fall Family Fun

Fall Family Fun

Westchester is your ultimate fall family destination! Apples, pumpkins, foliage, hayrides and more await your family.
Destinations
  • Stone Barns Center's Annual Harvest Fest
  • Annual Tarrytown Halloween Parade
  • The Great Jack O'Lantern Blaze
  • Stone Manor 101
  • The Westchester Marriott
  • Fall Crafts at Lyndhurst
  • Muscoot Farm

Adventure Seekers

Get your shoes muddy with a getaway full of kayaking, fishing, camping and hiking.
Destinations
  • L.L. Bean Outdoor Discovery School
  • Croton Point Park
  • Fishing in Croton Point Park
  • Anthony's Nose
  • Peekskill Coffee House
  • Where to Stay
Dobbs Ferry

Two Wheeled Fall Foliage

Norman E. Gaines, Jr.

Hop on your motorcycle and head to Westchester, minutes north of New York City.
Destinations
  • Historic River Towns
  • North to Westchester's Border, Where Eagles Soar
  • Parks, Reservoirs and Reserves
  • Motorcycle Shops (Just in Case!)
  • Where to Stay

Jazz and Soul Live Music

A day (or two) of diverse and intimate musical experiences awaits you in Westchester.
Destinations
  • Division Street Grill
  • The Quiet Man Public House
  • Inn on the Hudson
  • Holiday Inn Express Mt. Kisco
  • Aaron Copland House
  • Jazz Forum Arts

Famous Families

Since Henry Hudson's 1609 exploration, Westchester has been home to many famous and influential families.
Destinations
  • Sunnyside
  • Lyndhurst
  • Old Dutch Church and Burying Ground
  • Phillipsburg Manor
  • Kykuit - The Rockefeller Estate
  • Van Cortlandt Manor
  • Where to Stay
The Valley Table

Field to Pasture

Discover our many flavors with a visit to the restaurants, farms and breweries that make us a top destination for great food and drink.
Destinations
  • Stuart's Farm
  • Purdy's Farmer & the Fish
  • Wilkens Fruit and Fir Farm
  • Birdsall House
  • Crabtree's Kittle House Inn
  • The Cookery
Apple Picker's Paradise

Apple Picker's Paradise

Jon Chattman

This itinerary offers a few things you might want to do before and after your journey to the orchard.
Destinations
  • Rue de Crepes
  • Harvest Moon Farm & Orchard
  • Music Conservatory of Westchester
  • Harbor Island Park
  • Westchester Marriott
Tasting Tour & Picnic

Tasting Tour & Picnic

Taste the best of Westchester. Sample delicious local delicacies at each stop on this itinerary, culminating with a sunset picnic.
Destinations
  • Tarry Lodge
  • Crabtree's Kittle House
  • Mt. Kisco Smokehouse
  • Ward Pound Ridge Reservation
  • Sleeping accomodations

Westchester Without a Car

You don't need four wheels to enjoy a Westchester getaway. Discover the best of the Hudson River via mass transit.
Destinations
  • Metro-North at Grand Central Terminal
  • Tarrytown Waterfront
  • Tarrytown Farmers' Market
  • Old Croton Aqueduct Trail
  • Bistro 12
  • Tarrytown Music Hall
  • Doubletree by Hilton Tarrytown
  • Castle Hotel & Spa

Explore Northern Westchester

Discover rural splendor and cultural magnificence Westchester has to offer north of the Cross Westchester Expressway.
Destinations
  • Downtown Katonah
  • Katonah Museum of Art
  • Crabtree's Kittle House
  • Ward Pound Ridge Reserve
  • Wolf Conservation Center
  • Le Chateau
  • Caramoor Center for Music and the Arts
  • Where to Stay
Spooky Spectacular Trails

Spooky Spectacular Trails

Get ready to get scared! The home of The Headless Horseman, Westchester is the ultimate haunted Halloween destination.
Destinations
  • Washington Irving's Sunnyside
  • The Great Jack O'Lantern Blaze
  • Sleepy Hollow Cemetery Evening Tour
  • Castle Hotel & Spa
  • Jay Gould's House of Curiosities
  • Irving's 'Legend'
  • Horseman's Hollow

Naturally Beautiful Driving Tour

Get in the car and take in the foliage as you cruise the most colorful scenery in Westchester.
Destinations
  • Scenic Hudson Park at Irvington
  • Sweet Grass Grill
  • Graham Hills Park
  • Saw Mill River Parkway
  • Cross River Reservoir
  • Blue Dolphin Ristorante
  • Holiday Inn Mt. Kisco
Rockefeller State Park

Head to Sleepy Hollow

Headless Horseman

The Headless Horseman shares his favorite spooky spots to ride around town.
Destinations
  • Horsefeathers
  • Tarrytown Music Hall
  • Bridge View Tavern
  • Great Jack O'Lantern Blaze
  • Rockefeller State Park Preserve
  • Old Croton Aqueduct
  • Where to Stay

Everything Old is New Again

Hunt for vintage finds while antiquing and discover the charm of Westchester along the way.
Destinations
  • Le Jardin du Roi
  • Antiquing in Chappaqua
  • Little Crepe Street
  • Antiquing in Mount Kisco
  • The Rose Room
  • Holiday Inn Mt. Kisco
  • Crabtree Kittle House Inn

Yonkers for the Young at Heart

Whether you've got kids or you just want to feel like one, bustling Yonkers, NY is for you. Get ready to learn, discover and play.
Destinations
  • Hudson River Museum
  • Science Barge
  • X2O - Xaviars on the Hudson
  • La Bella Havana
  • Empire City Casino at Yonkers Raceway
  • Where to Stay