Sleepy Hollow Fall

Itineraries for Every Interest 

From seasonal getaways that let you explore the best of Westchester to one-day, one-town excursions, we’ve created itinerary suggestions for every interest and travel style.

 

Fall for Westchester 

Fall is magic in Westchester County. Visitors can enjoy a variety of indoor and outdoor activities throughout the season, as well as spooky events, making Westchester the ideal choice for an autumn escape.
 

Fall Leaves

Bike-and-Hike Leaf Peeping Weekend

Westchester County is an excellent place to experience Mother Nature’s spectacular fall display. Because the morning and late afternoon hours show the leaves in their best light, we’ve crafted an active, outdoor itinerary that puts you in the right spot at the right time to capture the magic.

Family-friendly Spots Along the Westchester Craft Beverage Trail

The lively Westchester Craft Beverage Trail has something for everyone featuring live music, food trucks, and games. Each of these scenic trail spots has a unique personality and is ideally located for the perfect fun-filled family-friendly stay where you can explore all Westchester has to offer.  

Sunnyside Evening

Harvests, Haunts and Howls: Fall Family Adventure

Autumn is a magical—and spooky—time in Westchester County. This wild and wonderful weekend makes the most of it all, from an apple-picking outing in the countryside to a celebration of one of America’s most “legendary” Halloween tales.

Family Excursions

Westchester is chock full of activities that appeal to all ages. Explore the changing seasons on a hike, challenge yourself on a ropes course, sample some delicious eats and visit a farm to pick-your-own seasonal fruits and vegetables. 

African American Heritage Trail

The African American Heritage Trail is a collection of historic sites that preserve and interpret the contributions that people of African descent have made to the development of this country's unique American identity. The Trail is an ongoing initiative to identify sites, buildings and locations that reflect both the actions and experiences of African Americans in the evolution of Westchester. 

Dog Friendly Westchester

A Tail Wagging Westchester Getaway

Bring your loyal companion along on a Westchester adventure, thanks to a plethora of pet-friendly hotels, parks, and restaurants.

   Other seasonal itineraries:

   Winter        Spring

 

Hyperlocal itineraries help you turn a short visit into a day beyond expectations.