Summer Arts & Culture
C O N C E R T S | T H E A T R E | M U S I C A L S | D A N C E | C O M E D Y
Summer has a way of slowing us down just enough to notice, and enjoy, the things that matter. Add live music, theater, dance, or performance to the mix, and those moments become even more memorable. The arts have a unique ability to spark imagination, expand young minds, and remind adults of the wonder, curiosity, and creativity that can so easily get lost in the rush of everyday life.
There are few better ways to spend a summer evening than under the open sky, listening to a concert, watching a play, or experiencing a performance that leaves you thinking long after the sun has set. And perhaps best of all, we are fortunate to have an extraordinary collection of cultural destinations right here in our backyard - and throughout the surrounding region. destinations right here in our backyard - and throughout the surrounding region. The following are some of our favorites, and we hope they inspire you to get out, explore, and make the arts a part of your summer.
CARAMOOR
Katonah, New York - Ticketed
One of the crown jewels of summer culture in Westchester, Caramoor combines world-class music programming with the romance of an Italianate estate in Katonah. Lawn concerts, jazz evenings, chamber music, and outdoor performances unfold across gardens and terraces that feel transported from Europe.
Live music happening on:
JULY: 2, 3, 4, 9, 10, 11, 12, 17, 18, 19, 23, 24, 25, 26
AUGUST: 1, 2
RIDGEFIELD PLAYHOUSE
Best known for bringing nationally touring musicians, comedians, and cultural programming to Fairfield County year-round, the Ridgefield Playhouse expands outdoors each summer with its popular Sunset Series, transforming the lawn into an intimate open-air concert venue.
Summer Outdoor Concerts (Live Outside)
July 31, August 1, August 2
SUMMER THEATRE OF NEW CANAAN
New Canaan, CT - Ticketed
A beloved local institution that brings professional- caliber musical theater to town each summer in a relaxed, family-friendly setting. This year’s season centers around the production — Matilda — running July 10–26, transforming the summer schedule into a concentrated few weeks of Broadway-style performances right in the heart of New Canaan.
WAVENY OUTDOOR SUMMER SERIES
New Canaan, Connecticut - Free
Free and open to the public! Blankets on the lawn, picnic dinners, and live music under the evening sky make Waveny one of the quintessential New Canaan summer rituals. Casual, social, and unmistakably local.
Every Wednesday June 17 - September 2 behind the Waveny Mansion.
JAZZ FORUM ARTS
Westchester County - Free
The highly respected jazz venue brings major talent to the Hudson Valley for locals to enjoy - for free throughout the summer!
• Every Wednesday: July 8 – August 26 (Waterfront Park, Dobbs Ferry)
• Every Friday: July 10 – August 28 (Pierson Park, Tarrytown)
• Every Tuesdays in August (Horan’s Landing, Sleepy Hollow)
• Every Thursday July 9 - August 27 (Matthiessen Park, Irvington)
• July 13 + 27, August 10 + 24 (Henry Gourdine Park, Ossining)
LEVITT PAVILION FOR THE PERFORMING ARTS
Westport, Connecticut - Ticketed
Westport’s beloved outdoor amphitrite offers a busy summer calendar, with free performances often taking place multiple nights per week. The lineup spans indie music, jazz, Americana, family programming, and nationally touring acts — all unfolding along the Saugatuck River in classic picnic-on-the-lawn fashion.
Concerts on: July: 8, 10, 17 & August: 9, 11, 23, 24
WESTPORT COUNTRY PLAYHOUSE
Westport, Connecticut - Ticketed
A historic theater institution known for thoughtful productions, literary programming, and elegant summer evenings out. The ivy-covered setting and longstanding cultural pedigree continue to draw audiences from across Fairfield County.
July 14 - August 1 - showing: Agatha Christie’s The Muder of Roger Ackroyd
FAIRFIELD THEATRE COMPANY
Fairfield, Connecticut - Ticketed
FTC punches well above its size, regularly attracting respected touring musicians and comedians in an approachable, low-key atmosphere. A favorite for spontaneous date nights and easy summer outings.
Concerts: July 3, 10, 16, 30
August 4, 6, 7, 13, 15, 16, 29
CAPITOL THEATRE
Port Chester, New York - Ticketed
The legendary Port Chester venue has become one of the region’s defining live music destinations, pairing historic grandeur with a consistently strong lineup.
Concerts: July 1, 3, 7, 8, 10, 11, 15, 16, 17, 19, 23, 25, 30, 31 & August 1, 9
SUMMER IN THE PARK
Stamford, Connecticut - Free
This longstanding Stamford summer tradition transforms Mill River Park into an accessible outdoor concert venue with family-friendly programming and major touring acts throughout the season. Casual and energetic, it’s one of lower Fairfield County’s easiest warm-weather nights out.
Concerts: July 16–19, 23–26, 30
THE PERFORMING ARTS CENTER AT PURCHASE COLLEGE
Purchase, New York - Ticketed
PAC brings internationally acclaimed musicians, dance companies, orchestras, and theatrical productions to an intimate and accessible setting. It remains one of the area’s most reliable destinations for high-caliber performance. Performances throughout the summer season
For those willing to venture a little farther, some of the Northeast's most celebrated summer arts destinations are surprisingly accessible from our corner of the world. Consider these the places worth planning a weekend around, or at least a very good excuse for a scenic drive…
WORTH A DRIVE:
HUDSON VALLEY SHAKESPEARE – GARRISON, NEW YORK ~35 minutes drive
Shakespeare, classic and contemporary theater, Ticketed
Set on a sweeping hillside overlooking the Hudson River, audiences are invited to picnic on the lawn before settling in for performances that consistently rival those of much larger metropolitan theaters.
Summer Performances: Ongoing June–September, with multiple productions rotating in repertory throughout the season.
BETHEL WOODS CENTER FOR THE ARTS – BETHEL, NEW YORK ~1hr 20min drive
Concerts, Ticketed
Located on the legendary site of Woodstock '69, Bethel Woods combines major touring acts with a sense of music history unlike any other venue in the region. The expansive outdoor amphitheater draws some of the biggest names of the summer concert season.
Summer Performances: Concerts scheduled throughout June–September.
TANGLEWOOD – LENOX, MASSACHUSETTS ~2 hour drive
Classical, pop, and chamber music, Ticketed
The summer home of the Boston Symphony Orchestra is one of America's great cultural destinations. Whether attending a world-class orchestral performance or spreading out a picnic blanket on the lawn beneath the Berkshire sky, Tanglewood is summer at its finest.
Summer Performances: Nearly daily programming from late June through Labor Day.
BARD SUMMERSCAPE – ANNANDALE-ON-HUDSON, NEW YORK ~1 hour drive
Opera, orchestral music, theater, dance, Ticketed
Intellectually ambitious and artistically adventurous, Bard SummerScape has built a national reputation for presenting bold opera productions, innovative theater, and exceptional musical performances. It rewards curious audiences looking for something beyond the expected.
Summer Performances: Festival runs July–August.
BASILICA HUDSON – HUDSON, NEW YORK ~1.5 hour drive
Concerts, experimental performance, film, multimedia arts - ticketed
Housed inside a dramatic 19th-century industrial factory, Basilica Hudson has become one of the Hudson Valley's most distinctive cultural venues. Contemporary music, visual art, film, and boundary-pushing performance attract creative audiences from across the region.
Summer Performances: Select events and concerts throughout June–September.
LITCHFIELD JAZZ FESTIVAL – KENT, CONNECTICUT ~1 hour drive
Jazz - Ticketed
A favorite among serious jazz fans and casual listeners alike, the Litchfield Jazz Festival brings internationally acclaimed performers to an intimate northwestern Connecticut setting. The atmosphere is sophisticated without ever feeling stuffy.
Summer Performances: Main festival weekend held July 24-26, with additional jazz programming throughout the season.
