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Activities to Enjoy

Leaf Peeping & Outdoor Exploration:

  • Westchester’s beloved summer tradition, Bicycle Sundays, runs through October, dipping into the fall season. It’s a great excuse to take advantage of the open road of the Bronx River Parkway and enjoy a 13.1-mile loop by bike, skate or foot.
     
  • Westchester's largest park, Ward Pound Ridge Reservation, offers the ideal setting for an afternoon adventure. With more than 4,000 acres of diverse terrain and 35 acres of wooded trails, it provides a stunning backdrop for enjoying the vibrant colors of autumn. It’s but one of the many parks that make up Westchester County’s 24,000 acres of parkland. Other great spots for catching the colors of fall include Teatown Lake Reservation in Ossining, Greenburgh Nature Center in Scarsdale, Edith G. Read Wildlife Sanctuary in Rye, Rockefeller State Park in Pleasantville and Tarrytown RiverWalk.
     
  • For an elevated leaf-peeping experience, consider hiking Anthony’s Nose. This moderate 2.6-mile hike features one of the greatest views of the Hudson Valley – a rock clearing overlooking Bear Mountain Bridge.
     
  • Experience the Hudson Valley’s seasonal transformation from a new perspective with Wings Air’s Fall Foliage Helicopter Tour. Fly high above iconic landmarks such as the Kensico Dam in Valhalla and Kykuit, the Rockefeller Estate in Sleepy Hollow and enjoy breathtaking aerial views of the changing landscape.

 

Fall Events:

  • From Sept. 6-8, Yorktown Grange is celebrating the 100th Anniversary of the Yorktown Grange Fair, a cherished community tradition since 1924. The fair features lively livestock exhibits, art shows, thrilling rides, and delicious food, bringing together generations for a memorable experience filled with fun, music and a deep sense of community.
     
  • From Sept. 13-15, art enthusiasts can immerse themselves in the world of craftsmanship at Lyndhurst’s Fall Craft Show. Held within the stunning Lyndhurst Mansion and its picturesque grounds, this event offers a chance to explore and purchase exquisite artworks from a variety of talented artisans.
     
  • Live music, BBQs, fruit picking and more make the farmlands of Westchester a social spot in the fall. Favorites farms known for their bounties of products and entertainment include Muscoot Farm in Katonah, Harvest Moon Farm and Orchard in North Salem, Stuart’s Fruit Farm in Granite Springs, and Wilkens Fruit & Fir Farm and Hilltop Hanover Farm in Yorktown Heights. For something a bit different, consider Yorktown Heights’ Faraway Farm Alpacas to meet their herd (also including Icelandic horses and donkeys). Their farm store is a treasure trove of gift ideas in advance of the busy holiday season, made from homegrown alpaca yarn.  
     
  • Spread throughout downtown venues between Sept. 11-15 in White Plains, JazzFest White Plains offers free and affordable musical entertainment.
     
  • Jay Day at the Jay Heritage Center will take place on Sept. 29 and is a beloved fall family festival featuring live music, stilt walkers, and jugglers, alongside activities like pony rides, a petting zoo and hands-on archaeology with Dr. Eugene Boesch.
     
  • On Sept. 29, Untermyer Gardens Conservancy will host Family Fun Day where families can enjoy a picnic in the beautiful Walled Garden, watch a magic show, fly kites, participate in scavenger hunts and more.
     
  • This fall, Caramoor will offer an engaging lineup of performances, presenting a wide range of cultural and artistic experiences. Samples include a presentation by Abdullah Ibrahim Trio in collaboration with Jazz at Lincoln Center on Nov. 8 and a benefit concert by folk supergroup Bonny Light Horseman on Dec. 7.
     
  • On Oct. 6, join the New Castle Historical Society for the “Castles of New Castle” tour where visitors can explore five stunning residences, including a unique Frank Lloyd Wright home.

 

Spooky Season Fun:

  • Celebrating two decades of family entertainment, The Great Jack O’Lantern Blaze rings in its 20th anniversary at Van Cortlandt Manor in Croton-on-Hudson. Held Sept. 13 – Nov. 17, a new feature for this year that complements the more than 7,000 illuminated jack o ’lanterns is the Gourd & Goblet Tavern, featuring libations, sweet and savory treats and “gourd-eous” decorations.
     
  • Explore the darker side of Lyndhurst Mansion with the Lyndhurst After Dark evening tour, available Oct. 17-20 and Oct. 24-27. Discover the mansion’s history and learn about its past inhabitants while viewing seasonal decorations and displays highlighting the superstitions of the era.
     
  • Sleepy Hollow, the birthplace of Washington Irving’s “The Legend of Sleepy Hollow”, is an ideal destination for those captivated by the spirit of the season. Visitors can explore the Old Dutch Church featured in Irving’s story and wander through Sleepy Hollow Cemetery, where the author and other historic figures are laid to rest.
     
  • The Armour-Stiner Octagon House in Irvington has long been shrouded in local legends linking its unique eight-sided design to the supernatural. This September and October, visitors can delve into its eerie history with two unique experiences: the Myths and Mysteries Tour, which explores the house’s rumored connections to the spirit world, and The Lady in White Tour, an immersive experience where a ghost story penned by a former resident unfolds around you.
     
  • Head to Sunnyside, Washington Irving’s historic Tarrytown home, to experience “Irving’s Legend” on select dates between September and November, a captivating outdoor performance by storyteller Jonathan Kruk. The event includes live music and a special appearance from the Headless Horseman.
     
  • This October, Tarrytown Music Hall invites thrill-seekers to its Ghost Tours, an immersive journey through the venue's haunted history. Guided by experts, visitors explore the historic corridors and uncover eerie stories and supernatural secrets of this iconic site.
     
  • Join the Twilight Village at Philipsburg Manor in Sleepy Hollow on select dates from Sept. 27 to Nov. 3. Explore a whimsical world where charming and mysterious characters will read fortunes, sing eerie melodies and spin captivating tales. Enjoy unique Sleepy Hollow souvenirs, savor cocktails and mocktails and indulge in tasty snacks for a memorable evening.
     
  • The Opus Spa in White Plains is embracing the Halloween season with its special Halloween Makeup Looks. Throughout October, the spa’s skilled makeup artists will craft fun and spooky styles for all Halloween parties.
     
  • Cross County Center invites families to a ghostly good time at the Halloween Spooktacular on Oct. 26. Enjoy a variety of activities including arts and crafts, a DJ dance party, inflatables, and performances by witches and wizards. There will also be spooky selfie spots and a trick-or-treat session for kids. The event is free, no registration is required, and it will take place rain or shine, with a rain location in the parking garage next to Macy's.
     
  • On Oct. 14, Rivertowns SUP & Yoga will host a unique "SUP Witches" event on the Hudson River for stand up paddleboarders. Participants are encouraged to don their best witch costumes and paddleboard along the scenic river, embracing the spooky spirit of the season. With stunning views and a festive atmosphere, it's a fun way to enjoy fall on the water. All levels are welcome, making it a perfect outing for both beginners and seasoned paddlers looking for a magical experience.

 

Arts & Culture:

  • The Hudson River Museum offers a rich cultural experience with engaging exhibits and events for visitors of all ages. Currently, the museum features "A Feast for the Eyes: Sumptuous Still Lifes," showcasing stunning still-life artworks that celebrate the beauty of everyday objects. Visitors can explore this exhibit along with the museum's diverse collection, all set against the backdrop of the scenic Hudson River.
     
  • The Katonah Museum of Art offers a dynamic array of exhibitions and programs that engage visitors with contemporary and historical art. Throughout the fall, the museum hosts mini classes where little artists and their grown-ups can explore new artmaking techniques inspired by the exhibits, fostering creativity together in a serene setting.

 

Where to Dine this Fall:

  • Embark on a tasty journey with the Westchester Craft Beverage Trail's free mobile passport. This curated collection leads enthusiasts to local breweries, distilleries, cideries and tap rooms, where local craft artisans introduce them to the region's finest beverages. Signing up is free and participants can earn points by checking in at participating spots, unlocking special rewards for a seamless and rewarding craft beverage trail adventure.
     
  • Hudson Valley Restaurant Week returns Oct. 28 through Nov. 10, making for an easy way to explore the best of Westchester dining, including its many Michelin-reviewed restaurants.
     
  • Westchester's dining scene is bursting with new and exciting flavors. Discover the latest culinary hotspots, including Bedford Post Tavern in Bedford, featuring a menu by James Beard Award-nominee Chef Sam Mason, and City Pizzeria in White Plains with its delectable thin-crust pies. In Irvington, Ludy Café and Don Carvajal Café offer exceptional coffee and pastries, while Dobbs Ferry’s Mirabella Cocina Latina serves up vibrant Latin American dishes. For a more casual experience, visit Ramen Musashi in Ardsley or enjoy Saint George Bistro’s affordable three-course menu in Hastings-on-Hudson.

 

Where to Stay:

  • Perched above Washington Irving’s Sunnyside, Tarrytown House Estate offers a glimpse into America’s Gilded Age on its 26-acre estate. This historic retreat combines elegant 19th-century mansions with modern amenities. Guests can enjoy seasonal Cantonese cuisine at Goosefeather, crafted by renowned chef Dale Talde.
     
  • The Abbey Inn & Spa, nestled along the scenic Hudson River, offers breathtaking fall views and a peaceful retreat. Located in a beautifully restored former convent, guests can enjoy the vibrant surrounding foliage, relax at the luxurious spa, and savor farm-to-table cuisine at the on-site restaurant, Apropos, now helmed by local celebrity chef Peter X. Kelly.
     
  • Castle Hotel & Spa in Tarrytown offers timeless elegance, set on one of the highest vantage points overlooking the Hudson River. Transport to another time thanks to its medieval style architecture, or look to get lost (in the best of ways) within its 10 serene, wooded acres.
     
  • Nestled in the charming town of Bedford, Bedford Post Inn is a quaint retreat that offers a serene escape with its rustic elegance and warm hospitality. Enjoy the crisp autumn air, explore the picturesque surroundings and relax in the inn’s inviting ambiance.
     
  • Located in Tarrytown, the Westchester Marriott is an excellent choice for its close proximity to popular events and attractions, offering convenient access to everything the region has to offer. Guests enjoy comfortable accommodations and easy access to local dining, shopping and entertainment.


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.
 

Farmers Markets

Visit a farmers market for great, fresh and locally produced and harvested food, including produce, meat and fish, baked goods, dairy and prepared food.

Wednesdays
Thursdays
Saturdays
Sundays
 

In the Arts

Check out ArtsWestchester’s Top 5 Arts Picks weekly for new arts events and cultural happenings throughout Westchester.

 

Virtual Activities