Best of Festchester

Ah, summer festivals! One of the biggest pleasures of summer is heading to an outdoor field, walking up to a tented vendor, buying some just-grilled food, and strolling along eating it while taking in the alfresco entertainment. If you plan your summer right, you can get your live music (classical, cabaret, jazz, rock, and even Celtic reggae), world-class theater, ethnic food, enviable crafts to purchase, and kids’ activities all from these seasonal extravaganzas. Here is our guide to local and nearby festivals.

Westchester County Heritage Celebrations
Kensico Dam Plaza, Valhalla
(914) 864-7275

Dates: Ongoing through August 23

Forget that city to the south of us—Westchester’s the true melting pot. Otherwise, it wouldn’t be able to sustain its popular annual Heritage Celebrations, which showcase the county’s different cultures through what we love best: food, music, performances, and crafts (but especially the food). Best of all: admission is free!

The Hudson Valley Shakespeare Festival brings Shakespeare outdoors.

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Hudson Valley Shakespeare Festival

Boscobel House and Gardens
Garrison, NY
(845) 265-9575

Dates: June 20 to September 6
When you see the awe-inspiring tent laid out on Boscobel’s beautiful grounds, you’ll think twice about getting your Shakespeare elsewhere. This year, the Bard’s Pericles and Much Ado About Nothing are performed in rotation, along with the Shakespeare-inspired mash-up, The Complete Works of Shakespeare (Abridged). Bring dinner—or order a meal and a bottle of wine directly from the Festival—since the grounds open two hours early for picnicking.

Caramoor International Music Festival
Caramoor Center for Music and the Arts, Katonah
(914) 232-5035

Dates: June 27 to August 2
This eight-week festival features music of every stripe almost every day, including performances from the resident Orchestra of St. Luke’s, intimate recital performances, family-friendly classical concerts, a two-day jazz festival, and more. Don’t miss the July 4 event, which features an outdoor pops concert of favorite tunes followed by Caramoor’s first-ever fireworks display.

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Entertainment Under the Stars at the Levitt Pavilion for the Performing Arts
40 Jesup Rd, Westport, CT
(203) 221-2153

Dates: June 28 to August 31
We like outdoor entertainment, but we love it when it’s free. The Levitt Pavilion hosts more than 50 nights of free entertainment. In one week, you can see a magic show, a ballet performance, a Celtic rock band, and a Broadway star singing country music—and not spend a dime.

Bard SummerScape
Bard College, Annandale-on-Hudson, NY
(845) 758-7900

Dates: July 9 to August 23
The groovy-looking, Gehry-designed Richard B. Fisher Center for the Performing Arts is this sprawling festival’s home, which somehow manages to incorporate classical music, opera, theater, film, and cabaret performances. The main event is the Bard Music Festival, which this year focuses on the life and music of Richard Wagner.

Pleasantville Music Festival

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Big Head Todd and the Monsters headline this year’s Pleasantville Music Festival.

Parkway Field, Pleasantville
(914) 714-2738

Date: July 11
This festival packs a summer’s worth of entertainment into one day, featuring three stages of musical acts in addition to a kids’ area. The headliner for this year’s main stage is the Colorado-based Big Head Todd and the Monsters; the band’s three Billboard chart hits include “Broken-Hearted Savior,” “Bittersweet,” and “Circle.” In addition, festival organizers have promised an expansion of the McArthur’s Beer & Wine Garden, which last year featured three bands playing in rotation.

Also consider:
The Untermyer Performing Arts Council holds its Spring Concert Series in Yonkers’s Untermyer Park every Saturday night from June 27 to August 29 (914-375-3435).


Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

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