Where to Eat, Explore and Enjoy Summer in Westchester County

WHITE PLAINS, N.Y. – May 22, 2025 – As the days grow longer and warmer, Westchester County comes alive with summer charm and fresh adventures for all ages. From family-friendly festivals and live music extravaganzas to scenic hikes, splash-worthy waterfronts and top-tier ice cream spots, it’s a go-to destination for summer fun. Just north of New York City and easily reached by car or Metro-North, Westchester County offers the perfect blend of nature, culture and community. The following travel ideas are courtesy of Westchester County Tourism & Film:

Summer’s Biggest Hits – Festivals, Music & More:

• Kick off summer with free admission to Playland Park all Memorial Day Weekend as Westchester’s iconic amusement park opens for the 2025 season, featuring entertainment and fun for all.

• The Port Chester Arts Festival returns on May 31, inviting visitors to explore a vibrant day of creativity and community. Local arts organizations, businesses and artists will open their doors for a dynamic lineup of exhibitions, open studios, performances and interactive events.

• Sleepy Hollow Music Festival takes place on June 7 along the scenic Hudson River offering a dynamic, family-friendly day of live music, local vendors and community celebration. The festival features a large kids zone and children 12 and under receive free entry.

• Westchester Magazine’s annual Wine & Food Festival returns June 3-8 with a weeklong celebration of the County’s vibrant culinary scene, set across the region. From gourmet tastings and wine pairings to chef demos and interactive workshops, the festival offers something for every food and wine enthusiast.

• Hudson River Music Festival plays June 14 at Croton Point Park, bringing together music, community and environmental awareness in a joyful, all-ages setting.

• Caramoor Center for Music and the Arts’ 80^th summer season runs from June 15 to Aug. 3 in Katonah, offering a rich lineup of classical, jazz and world music performances in Caramoor’s lush gardens and historic spaces – a true cultural highlight of the season.

• Cross County Center’s Summer Fest 2025 occurs June through August featuring a variety of events such as concerts, salsa nights, Zumba, ninja obstacle courses, art workshops and more, making it Yonkers’ go-to spot for outdoor summer fun.

• Gigante in Eastchester is turning up the heat with high energy, themed poolside parties all summer long. From the chic White Party on June 20 to the playful Flamingle on July 18, festival-inspired Gigante Coachella on Aug. 8 and the ultimate send-off, Summer Jam on Aug.29, each night features live DJs, curated cocktails, VIP tables and great vibes.

• The Hudson River Museum’s Summer Amphitheater Series runs Friday evenings from July 11 to Aug. 8, featuring a lively mix of music, dance and even falconry performances in a unique open-air venue overlooking their namesake river.

• The Pleasantville Music Festival returns on July 12, celebrating indie rock, national headliners like Dawes and local talent at Parkway Field. With family activities, a beer and wine garden and a zero-waste initiative, it’s a feel-good day of music for all ages.
• Jazz Forum Arts’ Outdoor Summer Concerts take place throughout July and August, bringing free jazz performances to scenic riverfront parks in Dobbs Ferry, Tarrytown, Sleepy Hollow and Ossining – perfect for a relaxing evening out by the water.

• Revolutionary Westchester 250 brings history to life this Sept. 27–28 with a festival at Croton Point Park, commemorating the County’s pivotal role in the American Revolution. Enjoy live reenactments, family-friendly activities and immersive educational programming – all part of a larger initiative leading up to the nation’s 250th anniversary in 2026. A second event will follow in Oct. at Ward Pound Ridge Reservation. 

Pride & Juneteenth in Westchester: 

• The Yonkers Pride Festival returns June 14, transforming the downtown waterfront into a joyful celebration of love, identity and unity. Expect live music, drag performances, family-friendly activities and vibrant community pride.

• Friday Night Pride lights up Hastings-on-Hudson on June 13, bringing together small-town charm and big celebration energy. This inclusive evening features live performances, art installations, kids’ crafts and Pride-themed specials at local restaurants.

• Queer Climbing Nights at Movement Valhalla offer a supportive, affirming space for LGBTQ+ climbers and allies to connect and move. These monthly events blend physical adventure with community and are part of Westchester’s commitment to wellness and belonging.

• Caramoor’s Juneteenth Celebration takes place on June 15, honoring African American heritage with powerful performances, music and storytelling set in Caramoor’s tranquil, historic gardens.

• ArtsWestchester will host county-wide events throughout June, featuring art exhibits, performances, educational programs and family-friendly activities that reflect the meaning and legacy of Juneteenth.

• Explore Westchester’s rich African American heritage through historic sites, annual events and vibrant arts and cultural experiences. Follow the African American Heritage Trail for an enlightening exploration of the County’s diverse and impactful history.

Adventure Awaits: 

• Bicycle Sundays returns as a beloved Westchester tradition. It closes a stretch of the Bronx River Parkway to traffic for walking, biking and family-friendly fun. It’s a scenic and active way to experience the County’s green spaces.
• The Tarrytown Lighthouse in Sleepy Hollow is now open to visitors after a major restoration. This gem, listed on the National Register of Historic Places, offers panoramic views of the Hudson River and a peek into maritime history – perfect for photo opportunities and quiet reflection.

• Step into the past with Historic Hudson Valley tours, featuring immersive experiences at landmarks like Philipsburg Manor, Washington Irving’s Sunnyside, Union Church of Pocantico Hills and Kykuit, The Rockefeller Estate. Don’t miss Lyndhurst in Tarrytown, a breathtaking Gothic Revival estate with guided tours, gardens and seasonal events that bring local history to life.

• Glow in the Park at Boundless Adventures in Purchase lights up the night with LED-illuminated ropes courses, upbeat music and adrenaline-pumping fun for all ages.

• Hudson River Recreation offers kayak and paddleboard rentals at multiple waterfront locations (not limited to the Hudson River), inviting visitors to explore the river at their own pace with guided or self-led options.

• From May through October, the Wolf Conservation Center (WCC) invites visitors to “Sleeping with Wolves” in South Salem – an unforgettable overnight experience beside the 20+ endangered wolves that call the WCC home. It’s wild, educational and one-of-a-kind.

• Westchester’s natural escapes offer scenic trails and peaceful picnic spots perfect for families and outdoor lovers alike. Croton Gorge Park in Cortlandt features easy trails, wide lawns and breathtaking views of the New Croton Dam – ideal for a relaxing hike or picnic. Mianus River Gorge in Bedford offers a more rugged trek through shaded woodlands and elevated terrain rich in plant life. Teatown Lake Reservation in Ossining boasts 15+ miles of trails and unique seasonal offerings like Wildflower Island, a guided walk through rare native habitats. For a full day of nature and discovery, visit the Greenburgh Nature Center – a 33-acre preserve with trails, ponds, gardens, a birds of prey aviary and over 100 live animals, plus indoor exhibits, a greenhouse and a children’s play area.

• Make a splash at Westchester’s beaches, from the sandy shores of  Rye Town Park & Beach and Playland Beach to Croton Point Park Beach in Croton-on-Hudson – perfect for swimming, kayaking and paddleboarding.

• Set sail with Port Sailing School in New Rochelle, offering rentals, lessons and a junior sailing camp for a safe and exciting day on the Long Island Sound.

• The Westchester Soccer Club at Memorial Field in Mount Vernon adds high-energy fun to the outdoor mix. Catch a match in this state-of-the-art venue as the County’s first United Soccer League team takes the field.

Sips, Scoops & Scenic Bites:

• Sip your way through the Westchester Craft Beverage Trail with a free mobile passport that guides visitors to local breweries, cideries, distilleries and taprooms. Check in, earn points and unlock rewards along the way at spots like Broken Bow Brewery in Tuckahoe, Croton Tapsmith, Hardscrabble Cider in North Salem and more.

• Cool off with Westchester’s sweetest stops, from King Kone in Katonah to The Blue Pig in Croton-on-Hudson and Penny Lick Ice Cream in Hastings-on-Hudson. Explore additional options like The Hudson Creamery in Peekskill, Bluebird Homemade Ice Cream in Cross River and Lost Borough Ice Cream in Yonkers.

• Alfresco season is in full swing, with garden and waterfront dining spots that serve up local flavor with a view. Enjoy lush garden settings at favorites like Nadine’s in Yorktown Heights, Amore in Armonk and Scalini Osteria in Bronxville. For riverfront vibes, sip and savor at Half Moon in Dobbs Ferry, Red Hat on the River in Irvington and newcomer The Sailhouse in Tarrytown. Along the Sound Shore, sunny tables await at waterfront staples like Tiki Beach Pier Restaurant and The Barley Beach House, both in Rye – perfect for a sunset toast or seafood feast.

Westchester Stays:

• SpringHill Suites Tuckahoe offers modern comfort in a convenient location and the Train to the Big Game package makes catching a Yankees game easier than ever. The deal includes two off-peak Metro-North tickets to Melrose Station (just three blocks from Yankee Stadium), complimentary breakfast, free parking and shuttle service to the Tuckahoe or Crestwood stations. It’s a hassle-free, home-base stay for sports fans looking to enjoy a game without the traffic.

• Discover the Bedford Post Inn, a serene luxury retreat in the heart of Westchester. This Relais & Châteaux property boasts eight beautifully appointed rooms, a yoga loft, gourmet dining and is the perfect escape with a touch of elegance and rustic charm.

• The Abbey Inn & Spa is set in a restored convent overlooking the Hudson River in Peekskill where guests can unwind at the full-service spa, dine at Apropos restaurant, and explore nearby parks and galleries and riverfront trails.

• Fresh off a major renovation, Sonesta White Plains is in the heart of the city’s downtown featuring modernized guest rooms, reimagined public spaces and enhanced amenities designed to serve both business and leisure travelers at the highest level.

• Tarrytown House Estate offers a unique blend of 19^th-century charm and modern amenities, set on 26 acres overlooking the Hudson River. Perfect for couples or families, the property features a pool, tennis courts and is located just minutes from its downtown Tarrytown and neighboring Sleepy Hollow.

Easy to Get Here, Easy to Explore:

• Getting to Westchester is quick and seamless – just 35 minutes north of NYC via Metro-North Railroad, with Amtrak stops in Yonkers, New Rochelle and Croton-on-Hudson.

• Fly into ease with proximity to three major airports, including Westchester County Airport in White Plains (HPN) with direct flights from key markets nationwide and offering the Hidden Disabilities Sunflower Program to support travelers.