Fall in Westchester and Greenwich means crisp mornings, colorful leaves, and weekends filled with pumpkin picking and apple orchards. The Georgio Reddington Team knows that clients, friends, and neighbors love celebrating the season close to home, so we’ve gathered the best spots nearby to enjoy hayrides, cider donuts, and armfuls of pumpkins. Whether you’re in Westchester or Fairfield County these farms are just a short drive away and perfect for family fun.
Top Pumpkin & Orchard Spots in Westchester
Outhouse Orchards – North Salem, NY
A Westchester favorite, Outhouse Orchards has a little bit of everything—pumpkin patches, apple picking, hayrides, and even a corn maze. The Georgio Reddington Team recommends arriving early, as weekends get busy with families looking for cider donuts and the perfect fall photos.
Harvest Moon Farm & Orchard – North Salem, NY
Located right next to Outhouse, Harvest Moon is packed with fall fun. From BBQ lunches to live music and a huge pumpkin patch, this orchard is a must-visit. The Georgio Reddington Team often hears from clients that this is one of their most memorable fall outings.
Stuart’s Fruit Farm – Granite Springs, NY
As one of the oldest family-owned farms in the county, Stuart’s offers a relaxed, authentic fall experience. Pumpkins, hayrides, and fresh-baked pies make this a tradition. The Georgio Reddington Team loves that there’s no admission fee—just pay for what you pick.
Wilkens Fruit & Fir Farm – Yorktown Heights, NY
Pumpkin picking begins in October, and the farm also features a corn maze, a bakery, and a country market. The Georgio Reddington Team recommends pairing your pumpkin adventure with a stop for hot cider and cookies.
Barton Orchards – Poughquag, NY
A bit further north, Barton Orchards is worth the trip. With live music, family festivals, and an enormous pumpkin patch, it’s a fall destination. The Georgio Reddington Team suggests making a full day of it by exploring the farm market and petting zoo.
Pumpkin Patches Near Greenwich, CT
Blue Jay Orchards – Bethel, CT
This orchard offers pumpkins, apples, and everything in between. Wheelbarrows make it easy to cart away big pumpkins, and the Georgio Reddington Team knows families appreciate the variety and space to spread out.
Bishop’s Orchards – Guilford, CT
A little farther but perfect for a weekend drive, Bishop’s offers pumpkin picking plus a well-stocked farm market. The Georgio Reddington Team loves recommending this spot for clients who want a true New England fall experience.
Silverman’s Farm – Easton, CT
Pumpkins, animals, and scenic views make Silverman’s a family favorite. The Georgio Reddington Team suggests calling ahead to confirm crop availability before heading out.
Sam Bridge Nursery & Greenhouses – Greenwich, CT
Right in town, Sam Bridge offers a charming pumpkin selection without the drive. The Georgio Reddington Team often points neighbors here for a quick, easy pumpkin fix close to home.
Tips from The Georgio Reddington Team
- Arrive early: Popular spots fill up fast, especially on weekends.
- Check websites: Hours, ticket requirements, and crop availability can change.
- Dress comfortably: Wear sturdy shoes and layers for outdoor picking.
- Bring a camera: Fall foliage plus pumpkins makes for the perfect family photo.
- Make a day of it: Pair pumpkin picking with lunch at a local café or a drive through backroads for peak foliage.
Celebrate Fall with The Georgio Reddington Team
At The Georgio Reddington Team, we believe fall is about more than pumpkins—it’s about building memories with family, friends, and community. Whether you’re searching for the perfect front-porch pumpkin or a scenic orchard to spend the day, our team is here to share local favorites and insider tips. Living in Westchester and Greenwich means you’re never far from seasonal traditions that make our region so special.
If you’re exploring more than pumpkins this season—like buying, selling, or renting a home—The Georgio Reddington Team is ready to help. Just as we guide you to the best orchards, we can guide you home.
