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Spend a Legendary Fall in Westchester

Gorgeous scenery. Long hikes with leaves crunching underfoot. Picking apples off the tree and pumpkins from the patch. These are some of the delights that await in Westchester this fall. Plan your trip for two or the whole family with these itineraries that celebrate the season, with a side of spooky fun.  

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.  

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. 
 

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.

Accessible Northern Westchester Charm

Westchester's lush northern landscape includes the town of Katonah, where great leaf-peeping opportunities and impressive cultural and historic finds make the perfect accessible leisurely exploration for all visitors. 

 

Accessible Rivertown Getaway

With the glorious backdrop of colorful autumn leaves, accessible foliage viewing opportunities await, as well as historic treasures, hikes and strolls that suit many levels of ambition and experience.

 

Car-Free Accessible Day in Rye

Westchester is easy to reach by public transportation. Take an accessible, family-friendly day trip to Rye and explore museums, gardens and charming shops and restaurants. 

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. 

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.

One town, one beyond-perfect day:

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

Sound Shore

The Sound Shore region, stretching about 36 miles, is an eclectic collection of towns and villages…

Mid County

Mid county is the beautiful and unique hub of Westchester that offers both rural beauty and urban…