Call Or Text Me Anytime 914-745-6669

8 Fun Fall Things to Do in Westchester This Weekend

Things to do in Westchester

Fall In Love With Westchester

As the crisp breeze of fall dances through Westchester, get ready for a weekend brimming with excitement, laughter, and memorable moments. Gather your family and friends and dive into the heart of the community, where the spirit of the season comes alive. 

There are so many amazing things to do in Westchester this weekend. Here are just a few things for you to check out…

Comedy Night At Grace Hall Club

Get ready for an evening filled with laughter! Hudson Valley’s finest comedians, including James Fongemie, Alex Kollar, Kim Berns, and Dayna Marie, will tickle your funny bone during Comedy Night at the Grace Hall Club. Prepare for a night of hilarious entertainment and endless smiles.

Cost: $20 – Click Here for details.

When: Friday, October 13, 7:30 p.m. – 11 p.m. 

Where: Grace Hall Club, Ossining

The Rocky Horror Picture Show

Follow Brad and Janet as they stumble into Dr. Frank-N-Furter’s eerie mansion, meeting eccentric characters and enjoying dazzling performances. Get your exclusive Audience Participation Kit when you purchase tickets for this cult classic and enjoy games and a costume contest with exciting prizes before the show! 

Cost: $15 – $25 – Click Here for details.

When: Friday, October 13, 11:30 p.m. 

Where: Tarrytown Music Hall, Tarrytown

Pelham Pumpkin Festival, Book Sale, 5K & Fun Run

Embrace the fall fervor at the Pelham Pumpkin Festival! Join the Pelhams Children’s Center in a delightful fundraiser featuring a 5k race, kids fun run, live music, pie eating contest, and the aroma of freshly baked apple cider donuts. It’s a day of endless family fun that will create cherished memories.

Cost: Ticket Prices Vary. Click Here for details and to register.

When: Saturday, October 14, 9 a.m. – 2 p.m. 

Where: Town House Park, Pelham

Sleepy Hollow Street Fair

Step into a world of spooktacular delights at the Sleepy Hollow Street Fair. Beekman Ave transforms into a vibrant outdoor market, featuring nearly 100 vendors offering delectable food, exquisite crafts, and much more. From haunted hayrides to Halloween parades, this fair is a celebration of all things eerie and exciting.

Cost: This is a FREE event

When: Saturday, October 14, 10 a.m. – 4 p.m. 

Where: Beekman Ave, Sleepy Hollow

Bedford Music Festival

Indulge in the beauty of fall at the Bedford Music Festival. Delight in live music, savor delectable offerings from local restaurants, and explore the Vendor Village showcasing Westchester’s local businesses. The legendary reggae band, The Wailers, will set the stage for an unforgettable community event.

Cost: $30+ – Click Here for details.

When: Saturday, October 14, 3pm – 9pm. 

Where: John Jay Homestead, 400 Jay Street

Coraline Movie Night And Super Awesome Artland! 

Immerse yourself in the enchanting world of Coraline at Jacob Burns Film Center. Follow Coraline’s adventures as she discovers a secret door to an alternate reality, and stay for the Super Awesome Artland! project where kids (and adults!) can craft their own seeing stone. Dress up as Coraline and win spooky prizes!

Cost: $9 – $16  –  Click Here for details

When: Saturday, October 14, 7:30 pm – 9:30 pm 

Where: Jacob Burns Film Center, Pleasantville

Fall Foliage Photo Walk At Rockefeller State Park Preserve

Embark on a scenic journey amidst the breathtaking fall foliage. Guided by photographer Heidi Fuhrman, capture the beauty of nature on this two-mile Photo Walk at Rockefellar State Park Preserve. Whether you’re an experienced photographer or a beginner, this walk promises an opportunity to connect with the season’s wonders.

Cost: Tickets $4. Parking $6 – Click Here for details.

When: Sunday, October 15, 10 a.m. – 12 p.m. 

Where: Rockefeller State Park Preserve

Celebrate Día De Los Muertos At Caramoor

Experience the vibrant Mexican holiday, Día de los Muertos, at Caramoor. Enjoy lively music, passionate dance performances by Calpulli Mexican Dance Company, arts, crafts, and delectable snacks. Bring your blanket, sit back, and immerse yourself in the colorful festivities.

Cost: This is a FREE event.

When: Sunday, October 15, 3pm – 5pm.

Where: Caramoor Center for Music and the Arts, 149 Girdle Ridge Road

Want To Share Fun Things to Do In Westchester?

CLICK HERE if you have an event you’d like to add, CLICK HERE if you have a business you’d like to feature,  or simply email us at Events@LiveAndPlayInWestchester.com to let us know all about it!

Mia Shervington

Mia Shervington

I’ve had the incredible fortune to move to this amazing community 20+ years ago, and I couldn’t imagine living anywhere else. When I'm not selling homes, you can find me enjoying our local parks or taking in the sunset over the Hudson River. I'll never stop my quest for the perfect hot donut, despite what my waistline may say. Nothing is better than a fresh ..hot...donut. When I'm not snacking my way up the river, I also enjoy the trails at Teatown Reservation and the views over Long Island Sound at of Rye Playland (officially known now as Playland Park...whatever...LOL). I’m looking forward to connecting with you soon! See you around town!
Mia Shervington

Mia Shervington

I’ve had the incredible fortune to move to this amazing community 20+ years ago, and I couldn’t imagine living anywhere else. When I'm not selling homes, you can find me enjoying our parks, taking in the sunset over the Hudson River, hiking the trails at Teatown and being a kid at Rye Playland (officially known now as Playland Park ... whatever ... LOL). See you around town!

Skip to content