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The Winter Concerts to Bookmark in Westchester County

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These Westchester venues have a handful of concerts lined up this season. You might want to add a ticket to your holiday wish list!

With the holidays in full-swing and the new year right around the corner, there’s so much to look forward to around the 914. How about adding a night full of live music and dancing to your list of winter festivities? Here’s a preview of upcoming concerts in Westchester.

Judy Collins

The award-winning singer-songwriter, Judy Collins will be presenting a Christmas concert series featuring songs from her six-decade career. Her latest release, Spellbound, is her first-ever album filled with originals. Her “Holidays & Hits” show at Tarrytown Music Hall is everything it sounds like; Judy curated a set list of classic holiday songs to serenade the crowd on Friday evening.

Date: December 9
Where: Tarrytown Music Hall, Tarrytown
Cost: $35-$65

Reggie Harris

Musician and storyteller Reggie Harris is putting on a sensory-friendly family event this Sunday at Caramoor. Harris will educate the audience about the Underground Railroad through uplifting songs and stories. He shares how the holiday season gave a sense of hope and an opportunity to escape. Come learn about one of the most important points in American history during this moving happening. Harris will be doing an earlier show at 2 p.m. that is not specifically designed for people who have sensory sensitivities.

Date: December 11, 2 p.m. and 4 p.m.
Where: Caramoor, Katonah
Cost: Children $10, Adults $20


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Dark Star Orchestra

If you have no plans for New Year’s Eve, here is an idea! Stop by The Capitol Theatre to catch this Grateful Dead live concert experience. The orchestra performs a unique set list for each show that’s based off of the Gratefeul Dead’s discography. Dark Star Orchestra is said to incapsulate the sound and energy of the Grateful Dead, which it displays during its sold-out performances all over the country, Europe, and the Caribbean.

Date: December 30 & 31
Where: The Capitol Theatre, Port Chester
Cost: $45-$100

Greensky Bluegrass

Greensky Bluegrass is a five-piece rock band that formed back in the 2000s. Their music, displayed throughout their eight albums, shows how the band matured and shaped their sound over the years. They’ve earned critical acclaim from some big names like Billboard, Parade, NPR, and Rolling Stone, which have recognized them for their unique tunes.

Date: January 13 & 14
Where: The Capitol Theatre, Port Chester
Cost: Starting at $30


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Umphrey’s McGee

This band, originally from Indiana, dabbles in multiple genres but leans more towards rock. The audience will be in for a treat as the band experiments with metal, jazz, electronic, and country, leaving each concert it performs at with a one-of-a-kind experience. Westchester will be the band’s fifth stop on its 2023 tour around the country, which also marks its 25-year anniversary.

Date: January 20 & 21
Where: The Capitol Theatre, Port Chester
Cost: Starting at $35


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Louis Prima Jr. and The Witnesses

Slip on your dancing shoes because Louis Prima Jr. and The Witnesses are heading over to Peekskill. The band, led by Louis Prima, Jr., is an upbeat, horn-driven, 10-member, New Orleans-style band. It’s known to bring the audience to their feet with its rowdy rock and blues music.

Date: February 11
Where: Paramount Hudson Valley Theater, Peekskill
Cost: $25-$35

Ivalas Quartet

The quartet is made up of violinists Reuben Kebede and Tiani Butts, violist Aimée McAnulty, and cellist Pedro Sánchez. The group has been changing the face of classical music as it focuses on celebrating BIPOC voices. The quartet was formed back in 2017 at the University of Michigan. This is a rescheduled concert that was originally planned for November 13.

Date: February 12
Where: Caramoor, Katonah
Cost: Starting at $30


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Los Lobos

Los Lobos began 50 years ago performing upbeat versions of Mexican folk music in restaurants and at parties. The band eventually found itself within L.A.’s punk and college rock scene, giving its members the push they needed to expand their musical presence. They’ve since won a Grammy, sold millions of records, and won awards. Grab tickets to watch these guys perform their music, which is influenced by rock, country, Tex-Mex, and R&B.

Date: February 17
Where: Paramount Hudson Valley Theater, Peekskill
Cost: Starting at $50

Shawn Colvin, Marc Cohn & Sarah Jarosz: Together in Concert

These three acts are coming together to give Tarrytown one special evening. Shawn Colvin, a three-time Grammy winner, is best known for her song “Sunny Came Home.” Marc Cohn won the Grammy for Best New Artist in 1992 and is best known for his classic hit “Walking in Memphis,” which debuted on his 1991 album. Sarah Jarosz is a 31-year-old, four-time Grammy-winning artist who released her debut album back in 2009.

Date: February 26
Where: Tarrytown Music Hall, Tarrytown
Cost: $55-$85

Related: Where to Eat in Westchester Before Heading to Rockefeller Center


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