R5 Summer Fun in Westchester: Activities and Events Taking Place Every Summer

Traditions become traditions for a reason. There are some activities we can partake in every summer, year after year, and never get sick of them. Here are 10 of our favorites, which we’ve deemed worthy of our seasonal Hall of Fame.

Photo by Gabe Palacio

(1) Caramoor International Music Festival
Caramoor Center for Music and the Arts Katonah
(914) 232-1252; caramoor.org

You might think of Caramoor as a destination for classical music only, but, between June 23 and August 8, when the International Music Festival rolls into town, it’s so much more than that. Sure, if you’re looking for classical music, the Orchestra of St. Luke’s is in residence and ready to perform works like Mendelssohn’s A Midsummer Night’s Dream, which they will do on opening night. But you can also find Balinese music performed by Gamelan Dharma Swara (June 27), an American roots music festival (June 30), flamenco dance (July 11), a bhangra night (July 25), a jazz festival (July 28), and gospel music (August 5). And come Fourth of July, there’s no better place to see fireworks than the beautiful Venetian Theater.

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Photo by Erik Jacobs

Clearwater performers David Wax Museum

(2) Clearwater Great Hudson River Revival
Croton Point Park, Croton-on Hudson
(845) 236-5596; clearwaterfestival.org

The Clearwater Great Hudson River Revival has been a Father’s Day weekend tradition since 1978, and, if your dad is anything like ours, he’d prefer a ticket to the festival over another tie or set of golf tees any day. And, with performers like Arlo Guthrie, Béla Fleck, Joan Osborne, Ani DiFranco, Dawes, Deer Tick, Jill Sobule, David Wax Museum, and Peter Yarrow all lining up to perform, who wouldn’t? That’s without taking into account the craft show, green living expo, environmental education workshops, puppet shows, stories, jugglers, and more performing throughout the rest of the festival grounds. With all that going on, it might be easy to forget to take a ride down the Hudson River Sloop Clearwater—but you shouldn’t.

(3) Greasy Nick’s Clams and Burgers
New Rochelle; (914) 636-5503
Don’t let the sign touting “Leno’s Clam Bar” outside this road-food shack fool you—locals call this “Greasy Nick’s,” and clams aren’t its only claim to fame. If you’re craving burgers topped with fried onions, hot dogs with sides of fries, and buttery corn-on-the-cob, this is the place to come—but only in the summer, because it isn’t open year-round. The anticipation definitely makes it better.

(4) Hudson Valley Shakespeare Festival
Boscobel, Garrison, NY
(845) 265-9575; hvshakespeare.org

Just over the border, the Hudson Valley Shakespeare Festival is set to start another season. This year’s rotating selection of plays includes Love’s Labour’s Lost, Romeo and Juliet, and The 39 Steps. But it doesn’t really matter what the plays are—everything the company produces is top-notch, and theater is only half of the appeal. The other half is enjoying an alfresco dinner on the grounds of the beautiful Boscobel, sitting in the shadow of the Federal-style house and gazing into a perfect view of the Hudson River. Shakespeare can take a back seat to mother nature, can’t he?

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(5) Kykuit Tours
Visitors Center: Philipsburg Manor Sleepy Hollow
(914) 631-3992; hudsonvalley.org

Technically, Kykuit is open during times other than the summer—but it looks best during the season, when the gardens are in bloom and you get the best view of the Hudson River. Go for the Selected Highlights tour, and you’ll spend more time strolling the various gardens of the Rockefeller Estate, including an Italian garden and a secret grotto, and you’ll get to see some of the Rockefeller family’s extensive contemporary sculpture collection to boot. Really, though, you’ll be jealous of those Rockefeller views.

(6) Longford’s Own-Made Ice Cream
Rye, Larchmont, Pleasantville, and Old Greenwich, CT
(914) 935-9469; longfordsicecream.com

Forget Cold Stone Creamery. Ben and who? When it comes to ice cream in the county, you can’t find anything richer, creamier, and more delicious than Longford’s. (It pains us to say it, but it even has Carvel—the ice-cream empire that started in a mid-century stand on Central Avenue—beat by a mile.) And, with more than 50 flavors of ice cream, gelato, sorbet, and frozen yogurt, you can make daily trips to the scoop shop without having to repeat yourself.

(7) Playland
(914) 813-7010; ryeplayland.org

Sure, it doesn’t have the most thrilling rides, but taking a spin on the wooden Dragon Coaster has been a rite of passage for Westchester teens going back to the late-1920s. And County Executive Rob Astorino has big plans to redo the park—a committee is actively looking at proposals now—so if you want to experience Playland the charmingly rundown way you remember it, you have to make sure to get a few more visits in before he sets a plan into motion. Don’t miss our favorite ride: the deceptively dizzying Derby Racer.

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(8) Red Hat on the River’s Rooftop
Bar & Lounge
(914) 591-5888; redhatbistro.com

Heading to the roof deck at Red Hat on the River doesn’t have to be a cocktails-only affair, but, with a view like that, who needs food? For the price of a drink, you get an uninterrupted view of the Hudson River, Tappan Zee, and Palisades—and the best spot to watch the sun set in the county.

(9) Walter’s Hot Dogs
Mamaroneck; waltershotdogs.com
Walter’s has been serving his brand of split-down-the-middle dogs since 1919—and getting every kind of award or accolade a hot dog can get ever since. (It’s continually voted into our Best of Westchester issue.) Gourmet even named it the best hot dog in the country. Maybe it’s the blend of beef, pork, and veal; maybe it’s the secret mustard/relish sauce; or maybe it’s the kitschiness of sidling up to the pagoda-shaped stand and asking for a hot dog; but we believe that Walter’s lives up to the 93 years of hype.

(10) Donald M. Kendall Sculpture Garden
PepsiCo HQ, Purchase
We don’t know about in life, but the best things in summer are free. At least a visit to the Donald M. Kendall Sculpture Garden, on the campus of the PepsiCo headquarters, doesn’t cost a dime. What other museum in the world would let you look at works by Alexander Calder, Henry Moore, Isamu Noguchi, Louise Nevelson, Claes Oldenburg, and Auguste Rodin without charging admission? And, it being spread out over 168 acres, you can spend all day strolling from sculpture to sculpture (and enjoy a mean picnic while you’re at it—see page 56 for advice on what to bring on one).


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