Westchester County is the perfect place to enjoy all that summer has to offer, from outdoor festivals to community celebrations. As a local real estate expert, I’m excited to share some great events happening throughout the month of June 2025 in Westchester County, making it the ideal place to live, work, and play. Whether you’re a Westchester resident or considering moving to the area, here are some exciting events to mark on your calendar!
1. Westchester Annual Strawberry Festival: June 7th - Chappaqua
Kicking off summer in style, the 88th Annual Strawberry Festival in Chappaqua is a must-see event. This beloved festival offers something for everyone, including:
- Live music performances
- A bounce castle and petting zoo for kids
- A slime bar for the little ones
- Delicious strawberry shortcake and other festival food
- Local vendors showcasing crafts and goods
This family-friendly event is a perfect way to embrace the start of summer in Westchester County!
Tip: If you're thinking about moving to Chappaqua, this event gives you a taste of the community's friendly atmosphere.
2. Hudson River Music Festival: June 14th - Croton-on-Hudson
The Hudson River Music Festival on June 14th at Croton Point Park is a fantastic way to enjoy live music while surrounded by the stunning natural beauty of the Hudson River. Highlights include:
- Performances by the Rock and Roll Playhouse
- Creative puppet shows by Arm-of-the-Sea
- Interactive art workshops for all ages
- Family-friendly activities and games
With so much to do, this is one event that brings the community together to celebrate music and nature.
3. Sleepy Hollow Music Festival: June 7th - Sleepy Hollow
For music lovers, the Sleepy Hollow Music Festival on June 7th is an unmissable event. Held in the historic Sleepy Hollow, this festival features:
- 12 live bands across two stages
- Over a dozen food trucks offering delicious eats
- An expanded beer garden with local craft breweries
- A dedicated Kids’ Zone with fun activities for the whole family
This festival is perfect for anyone looking for a vibrant community atmosphere with great food, music, and family-friendly entertainment.
4. Bicycle Sundays at the Bronx River Parkway: June 1st, 8th, 15th, 22nd, 29th
If you love outdoor exercise or simply enjoy a leisurely ride, don’t miss Bicycle Sundays along the Bronx River Parkway. This event takes place on select Sundays throughout June (1st, 8th, 15th, 22nd, and 29th) and offers:
- A 6.5-mile stretch of the parkway open to bicyclists, skaters, joggers, and walkers
- A fun, car-free space to enjoy the outdoors
It’s a great way to connect with nature and stay active during the warmer weather months.
5. New Rochelle Pride Festival: June 7th - New Rochelle
The New Rochelle Pride Festival, held on June 7th, celebrates diversity and inclusivity in Westchester County. This vibrant event includes:
- Carnival games and entertainment
- Delicious food vendors
- Live music and performances
- Art and community booths
It’s an uplifting event that celebrates the LGBTQ+ community and fosters unity across all residents of New Rochelle and Westchester County.
6. Rose Day at Lyndhurst: June 8th - Rye
If you appreciate beautiful gardens, don’t miss Rose Day at Lyndhurst on June 8th. This event is held at the stunning Lyndhurst Estate in Rye, where you can:
- Wander through the famous rose garden
- Attend garden-related workshops
- Enjoy a relaxing day surrounded by nature
This is a perfect outing for those who love nature, history, and the outdoors.
7. Westchester Magazine’s Wine & Food Festival: June 3rd-8th - Westchester
Foodies and wine lovers will want to mark their calendars for the Westchester Magazine’s Wine & Food Festival from June 3rd-8th. This week-long event showcases:
- Gourmet food tastings from local chefs and restaurants
- Exclusive wine pairings with renowned sommeliers
- Interactive cooking demonstrations
- A variety of wine and food workshops
Whether you’re a culinary enthusiast or a wine connoisseur, this event offers a taste of the best in Westchester County’s dining scene.
Why Westchester County is the Ideal Place to Live
As a real estate professional in Westchester County, I can tell you that the area is not only known for its rich history and natural beauty but also for its vibrant local events. Whether you’re looking to buy a home in Chappaqua, Sleepy Hollow, Rye, or any of Westchester's charming towns, there’s something for everyone here. From outdoor festivals to cultural celebrations, these events provide a great way to immerse yourself in the community and get a feel for life in Westchester County.
If you're considering moving to Westchester or buying a home in the area, feel free to reach out. I’d be happy to help you explore the neighborhoods in Westchester County that match your lifestyle. Contact me, Amie Pisano, today. Let’s connect and start your journey to your dream home in Westchester!
📧 Email: [email protected]
📞 Phone: 914-715-2632
