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Caramoor Summer Sunset

Activities to Enjoy

Summertime Happenings:

  • Westchester Magazine’s annual Wine & Food Festival returns June 4-9 and will feature the County’s finest plates and pours along with award-winning chefs to celebrate all of the culinary wonders of Westchester County.
  • The 2nd annual Port Chester Arts Festival will return on June 1. Local arts organizations, businesses and artists will open their doors for a day of events, exhibitions, open studios and performances.
  • Join Cross County Center on May 18 for a 70th anniversary celebration that will take shoppers back to 1954 when the iconic outdoor mall first opened. Activities include strolling entertainers, music and selfie stations, a pop-up roller skating rink and more. Admission is free.
  • Over 60,000 participants make Bicycle Sundays a beloved Westchester tradition since 1974. Participants are encouraged to get outside to bike, skate, scooter, walk or jog the 13.1-mile loop of the Bronx River Parkway.

Live Music:

  • Sleepy Hollow Music Festival will take place on June 8 at Kingsland Point Park, including a tasty food and beverage scene. Discover why outdoor concerts in picturesque settings make Westchester a music lover's paradise and enjoy performances from headliners such as Cold War Kids, Danielle Ponder and more. Tarrytown House Estate’s Sleepy Hollow Music Festival Package offers exclusive perks including two complimentary tickets, early check-in, late check-out, weekend DJ entertainment s at Goosefeather restaurant and guaranteed reservations for Sunday Brunch at the Winter Palace with live music by Jono Manson.
  • The Pinkster Festival, a day of art, poetry, live music, dance and storytelling that celebrates and commemorates the region’s African American history and culture, returns to Philipsburg Manor on May 25.
  • Caramoor's summer season runs from June 9 to August 10, offering over 40 concerts spread across the property’s gorgeous grounds. Note: There is a free shuttle from Metro-North Railroad’s Katonah train station to and from Caramoor running throughout the summer season.
  • On July 13, the annual Pleasantville Music Festival takes place at Parkway Field. In addition to headliners, breakout stars and local artists, there will be a beer and wine garden, fun activities for kids and a zero-waste program to keep the Earth happy, too.
  • Jazz Forum Arts will host free outdoor Summer Concerts at five locations in Dobbs Ferry, Tarrytown, Sleepy Hollow and Ossining. The 32 concerts will take place throughout July and August, with varied midweek dates.
  • Other toe-tapping music festivals and events throughout the summer include Rock The Block in White Plains, Sunset Jazz Concerts at Lyndhurst Mansion in Tarrytown, the Yonkers Waterfront Live Summer Concert Series, Goosefeather’s annual Summer Lawn Parties in Tarrytown and the annual Scarsdale Music Festival, scheduled for June 1.

Celebrate June Pride:

  • The Yonkers Pride Festival returns on June 8 and will feature live music, street vendors, activities, numerous community organizations and a lively parade.
  • On June 13, Rockefeller State Park Preserve will host a Pride Outside Sunset Hike with OUTwalking, an outdoor hiking and walking group for the LGBTQ+ community.
  • Cross County Center in Yonkers will host a Pride-themed Zumba class in June. More details to come.
  • The Village of Hastings-on-Hudson will host the third annual Friday Night Pride, a free, joyful, family-friendly Pride festival in downtown Hastings on June 7. The event centers on a concert in the middle of Warburton Avenue, featuring a bevy of musicians, dancers, and performers, ranging from local talent to Broadway stars. The show will be emceed by stage and recording artist Amy Lynn of Amy Lynn & the Honey Men. A giant rainbow slide, kids’ crafts and more will be complemented by Pride-themed specials by local Village restaurants.
  • Celebrate Pride with the Katonah Museum of Art from June 29-30. Admission is free and visitors are invited to participate in a special Pride-themed art project in the Pollack Family Learning Center.
  • Join Wolf and Warrior Brewing Company in White Plains every Wednesday evening for Drag Bingo.
  • Join The Cliffs Valhalla for Queer Climbing Night, held every first Monday of the month, with additional meetup times starting in June. This inclusive event welcomes LGBTQ+ individuals and allies to come together, climb, train and connect in a supportive environment.

Juneteenth Events:

  • On June 16, Caramoor will host a special performance by Charles Turner & Uptown Swing to celebrate Juneteenth followed by family-friendly activities to complete this annual June jubilee steeped in tradition and joy.
  • The Juneteenth Celebration in Ossining awaits at Louis Engel Waterfront Park on June 22. Join in for an afternoon filled with culture, history, fellowship and a myriad of engaging activities.
  • Uncover Westchester's rich African American heritage with a journey through its historical sites, annual events, vibrant arts and culture. Follow the African American Heritage Trail for an enlightening exploration of the County's diverse and impactful history.


Great for Families:

  • The Tarrytown Lighthouse in Sleepy Hollow has completed an important two-year restoration project, and will be open to visitors this summer, making the perfect spot for exploring and grabbing a family photo.
  • From May through October, the Wolf Conservation Center offers a "Sleeping with Wolves" event where guests can camp out overnight with the 20+ wolves that call the WCC home.
  • Discover Westchester's shaded hiking trails, such as Mianus River Gorge Preserve in Bedford, offering a scenic 40-foot elevation above the river—a perfect family-friendly outing. In Cortlandt, enjoy an easy two-mile hike at Croton Gorge Park, boasting stunning vistas of the New Croton Dam.
  • Explore Westchester County's beach scene and experience the beauty of Long Island Sound at Rye Town Park & Beach and Playland Beach, both offering easy water access from Rye. For views and ample space head to Croton Point Park Beach in Croton-on-Hudson, where water enthusiasts can enjoy swimming, kayaking, boating and stand-up paddleboarding.
  • Sail throughout the Long Island Sound with Port Sailing School, located at the New Rochelle Municipal Marina. Enjoy rentals, lessons and a junior sailing camp for a safe and exciting day on the water.
  • Enjoy a family adventure at Playland in Rye, known for its historic rides, beachside setting and captivating Art Deco architecture. This summer, catch fireworks displays on multiple occasions, including July 4, and attractions like a waterfront slide, paddle boats and a pool area. Enjoy a meal at the renamed "Tiki Beach" restaurant on the pier or unwind at the Captain Lawrence Beer Garden.
  • Grand Prix New York Racing & Entertainment now offers ‘The Night Ride’ – where adrenaline meets illumination on the go-kart racetrack and participants can follow the guiding lights of the red trackers to show them the way.

Seasonal Dining:


Where to Stay:

  • The well-appointed Westchester Marriot Hotel in Tarrytown features modern lodging and two restaurants, Coopers Mill and Ruth’s Chris Steakhouse. Its location offers easy access to historic destinations like Historic Hudson Valley’s Lyndhurst Mansion, Washington Irving’s Sunnyside and Kykuit, the Rockefeller Estate.
  • Discover the reimagined Royal Regency Hotel in Yonkers, perfectly positioned near the scenic Hudson River, local parks, restaurants and the Empire City Casino, celebrating its 30th anniversary this year.
  • Enjoy 20% off a stay of three nights or more at Hotel NoMa in New Rochelle. Dive into summer fun as the pool opens for the season, followed by live music and entertainment at the on-site restaurant and lounge, NoMa Social.
  • Coming in 2024, Crotonville Hotel and Conference Center will feature 248 well-appointed guestrooms and over 70,000 square feet of meeting space.
  • Tarrytown House Estate offers luxurious lodging and extensive leisure facilities for summer enjoyment. Guests can relax by the outdoor pool or enjoy recreational activities like tennis, basketball and horseshoes.

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.




In the Arts

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


Virtual Activities