I lived in Westchester County for over 30 years, so I’m well aware of the pleasures of this wooded, hilly, sophisticated county. Flanked by Long Island Sound and the Hudson River. Westchester is made up of big cities, small towns, villages, farms, and miles of natural beauty.
Just 30 miles north of downtown New York City, it offers a terrific getaway, and a delightful, close-by add-0n to a NYC vacay or business trip. The county is easily accessible by major interstate highways and parkways, its own regional airport, Amtrak and three commuter rail lines, and is home to more than 40 hotels and conference centers.
Here’s a sampling of Westchester’s seasonal pleasures:
The 146th annual Westminster Kennel Club Dog Show will return to the historic Lyndhurst Mansion in Tarrytown, America’s finest Gothic Revival mansion, from June 18 through June 22. On July 9, the 16th Annual Pleasantville Music Festival takes place at Parkway Field, with headliners, breakout stars and local artists.
Caramoor’s Jazz Festival is a highly anticipated highlight of the County’s summer schedule amid the lush gardens Katonah’s marquee center for music and art.
Jazz Forum Arts will host free outdoor Summer Concerts in Dobbs Ferry, Tarrytown, Sleepy Hollow and Ossining. The 32 concerts will take place through July and August.
Untermyer Gardens Conservancy will host its second annual Minnie Untermyer Concert Series through September 4 in the amphitheater in the magnificent Walled Garden and overlooking the length of this monumental Indo-Persian space.
Four premier art organizations including Jacob Burns Film Festival, Historic Hudson Valley, and Caramoor Center for Music and the Arts have joined together to offer the Hudson Valley Summer Arts Pass.
Sleepy Hollow’s Kykuit is home to four generations of the Rockefeller family, with sweeping river views; the historic site of the National Trust for Historic Preservation is open through Nov. 13, 2022 for guided tours.
Westchester history shines at Washington Irving’s Sunnyside, Philipsburg Manor, The Union Church of Pocantico Hills, or with a Historic Homes and Landscape tour of the eight-sided Armour-Stiner Octagon House, a National Historic Landmark.
The iconic Hudson River Sloop Clearwater, which underwent a major overhaul, will be cruising throughout the Hudson Valley between Albany and New York through October, docking in Ossining and Yonkers.
Bicycle Sundays is a beloved Westchester tradition since 1974, where participants bike, skate, scooter, walk or jog the 13.1-mile loop of the Bronx River Parkway. Another option is Gotham Bicycle Tours, along The Empire State Trail, a 750-mile traverse designed for bicyclists and hikers to explore New York State.
Mianus River Gorge Preserve in Bedford is a trail that looms 40 feet above the Mianus River. And at Croton Gorge Park in Cortlandt, an easy two-mile hike includes gorgeous vistas of the New Croton Dam.
Rockefeller State Park Preserve in Mount Pleasant, offers horse-riding, walking, jogging, running, bird-watching, and fishing. I spent many years walking daily on its magnificent fields and hills. Today it includes a farm and education center and a world-class farm-to-table restaurant, Blue Hill at Stone Barns.
Teatown Lake Reservation will offer Wildflower Island Guided Tours throughout the season giving an in-depth look at the unique ecology of the sanctuary.
On Long Island Sound, beach options include Rye Town Park & Beach, and Playland Beach, both offering water access from Rye. On the Hudson River, Croton Point Park Beach in Croton-on-Hudson is popular for its scenic views and spacious beach, as well as kayaking, boating and stand-up paddle boarding. Adventure seekers can explore the 508-acre Croton Point Park.
Or sail throughout the Long Island Sound with Port Sailing School, at the New Rochelle Municipal Marina.
Playland, in Rye, is renowned for its historic rides, beachside setting, and Art Deco architecture. The park offers thrill rides as well as family-friendly options.
Notable Places to Eat and Drink
Cool treats include Bigfoot Creamery in Ossining, King Kong in Katonah, The Hudson Creamery in Peekskill, Ice Cream Social in White Plains, and Main Street Sweets in Tarrytown. For a different sort of sweet, Baked in Color launched in Larchmont this spring – with colorful cookies.
Outdoors, enjoy pleasant weather at 3 Westerly Bar & Grill in Ossining, Apropos Restaurant & Bar at The Abbey Inn & Spa in Peekskill, RiverMarket Bar & Kitchen in Tarrytown, The Bit in Dobbs Ferry, or Harvest on Hudson in Hastings-On-Hudson.
At Eastchester Fish Group in Scarsdale, you can shop at the fish market or enjoy a fine-dining experience; Tipsy Taco Bar has authentic Mexican food in Mount Kisco; and Wood & Fire Neapolitan Pizza in Pleasantville and Scarsdale offer hand-tossed pies.
For outdoor happy hours: Bartaco in Port Chester; Captain Lawrence Brewing Co. in Mount Kisco; Freebird Kitchen & Bar in White Plains; Le Fontane in Katonah; and even BXVL Coffeehouse in Bronxville, which offers a European-style happy hour featuring music, cocktails, aperitifs and small plates.
Where to Stay
The Opus is Westchester’s newest contemporary lifestyle hotel in the heart of White Plains.
Westchester Marriot Hotel in Tarrytown features modern lodging, plus easy access to destinations like Historic Hudson Valley’s Lyndhurst Mansion, Washington Irving’s Sunnyside, and Kykuit, the Rockefeller Estate.
On a hillside overlooking the Hudson River Highlands, The Abbey Inn & Spa is a former convent turned boutique hotel, with over 50 acres of scenic walking trails.
Set on 26 acres, Tarrytown House Estate offers luxurious lodging and amenities with extensive leisure and recreational facilities. The resort is home to Goosefeather, offering outdoor dining and Cantonese cuisine by celebrated chef Dale Talde.