Get a Little Bit Country This Christmas With Jessica Lynn

Westchester might not jump to mind as quickly as Nashville when you think of country music Meccas, but the Hudson Valley has long had a history of folk and steel-string twang, from Woodstock up North to Pete Seeger’s famed Clearwater Festival right here in Croton. And if you weren’t already a fan, one of country’s hottest up-and-coming performers just happens to be from Yorktown.

Read More: The Coolest Young Musicians Coming out of Westchester Right Now

In the last 5 years, Jessica Lynn has completed multiple national and international tours, and three full-length TV concert specials — all filmed locally at the the Winery at St. GeorgeThe Paramount Hudson Valley Theater, and most recently Peekskill’s Dramatic Hall. In that time she’s played alongside huge talents like Paul Simon, ZZ Top, Shenandoah, and Lonestar, worked with industry-leading producers, and released two EPs, each with nationally charting singles. 

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Photo courtesy of Jessica Lynn

On Saturday, December 14, Lynn will return home to perform her own holiday tradition, “A Very Merry Country Christmas” holiday show at Peekskill’s Paramount Hudson Valley Theater. Hosted by KICKS 105.5, Holiday Inn Express, and presented by DAS Auto Parts, The show will feature a list of Christmas classics and some newer pieces, including Lynn’s first-ever Christmas single Santa You Can Skip Our House

Guests can also expect local singers, dance schools, family-friendly surprises, and if you’re good, maybe even a visit from Saint Nick himself. As always, in what has become Toys for Tots Westchester’s biggest fundraiser of the season, the Westchester County Marine Corps will also be on-hand providing a special thank-you gift to any guests donating an unwrapped present.

This year also marks the addition of additional performers and back-up instrumentation, more pagentry and set staging, and an expanded one hundred kid choir.

“We’re turning up the volume on everything,” Lynn says.

In another fun new partnership, local ice cream giant Carvel has joined in to create a limited edition Jessica Lynn Holiday Dasher at the brand’s Cortlandt location, chock full of crushed candy canes, hot fudge, and Carvel’s iconic chocolate crunchies. Purchasing one enters you to win a pair of concert tickets and backstage passes to the holiday show, but you can also enter — and get a free download of Santa You Can Skip Our House — by donating a gift to Toys for Tots as the location will also be serving as a designated donation drop-off for the event. 

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Seeing as she’s a local, Lynn was obliging enough to sit a spell with us as she preps for the big show.

Photo courtesy of Jessica Lynn


First and foremost, we’ve gotta ask: How did a kid from Yorktown grow up to become an internationally recognized country sensation?

Hard work! Really hard work. Everybody thinks that show business is glamorous and I show up and I sing and that’s what I do. Really the work begins with the sixteen hours a day that I’m in the office trying to get my name out there. I always had really really big dreams and I personally believe that at a certain point it’s not about how talented you are, it’s the ability to get knocked down, kicked in the face, dirt thrown on you and be like, “Okay, I’m going to try this again tomorrow.”

Even just being from New York, there was so much resistance to me down in Nashville, like, “Oh, you have to move here if you’re going to be successful,” and “Your band doesn’t sound anything like what’s coming out of Nashville right now. And I was like, “Okay. Watch me.” I paid myself to film my first television special with a cheap local camera crew and it wound up going nation-wide on TV. That’s how my whole career started!

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You’ve toured and shared stages with the likes of Brad Paisley, Keith Urban, Hank Williams Jr., Lonestar, and Loretta Lynn. What have you taken away from performing with such legendary acts?

That has been really really such an incredible aspect of what we’ve gotten to do so far.

Country music is great because the people generally are so nice and down-to-earth. One of the first festivals we ever played, Montgomery Gentry’s dressing room was right next to mine and they literally came and knocked on my door and were talking to me, and I had no idea it was them just because I didn’t expect them to be so friendly and, you know, hanging out! I think getting the experience of being with these people has really shown me what to do and what not to do, how to behave and treat people with respect and be grateful for opportunities.

Just seeing performers who have been out there so much longer than you doing it, and seeing how they interact with a crowd or do their meet-and-greets … I’ve learned so much about just being on the road and being with people from watching people with so much experience do it.


Well, it’s definitely been working to your benefit. Your singles Crazy Idea and Let’s Don’t have both broken the Top 50 country charts, outperforming artists like Kenny Chesney in the process.

Yeah! I’m so excited! Let’s Don’t hit #45 and Crazy Idea peaked at 48. That was actually the first single I ever released to country radio, so for it to do so well … I really just can’t describe the feeling. As a little girl that always sang and performed and wanted to do this when I grew up, you always hope to have a hit single. For the start of my career to have gone so far … every week you’re getting notifications at 75, 60, like “Wow! We’re getting pretty close to 50!” The week we were approaching 50 I remember getting the email and being afraid to open it! It’s so exciting, especially since we’ve done it in such an unconventional way.

You can do whatever you want to do if you work hard enough and you believe. You really can chase your dreams and if it’s meant to be and you work hard enough it will be.


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How did “A Very Merry Country Christmas” get started?

This is going to be our fourth annual Toys for Tots Christmas concert at the Peekskill Paramount, and I always loved Christmas music. So when we decided to do it, it was such a learning curve. I didn’t know how difficult Christmas music is to play! But being up there, there’s just something about the holidays, about Christmas music, and we involved a lot of local kids and choirs and dancers and it was such a joyful, happy feeling in the theater that night that I was hooked. The second year it got a little bit easier and it got a little bit bigger. [In 2017] it actually became Toys for Tots’ biggest fundraiser of the whole season.


You also just released your first Christmas Single, Santa You Can Skip Our House ahead of the concert last year. How were you inspired to join the long tradition of country Christmas ballads?

Now that we’ve got this under our belts, I thought, “Let’s do something extra special to elevate it.” While my husband and I were doing one of our radio tours, we started humming this little Christmas thing and it developed. We decided to just go for it and we released it to radio and it charted. In its first day it was the #4 most downloaded song by radio stations and we came in #9 for the week with company like Garth Brooks and Brad Paisley. It was just so exciting and we weren’t even in December yet!


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Since last year’s show you’ve filmed a third special in Westchester and done several more U.S. and European tours. We get why you’re taking the Christmas show as sort of a working vacation.

Yes! I’m exhausted! [Laughs] I’m a very competitive person so since we were the biggest fundraiser last year we better top it this year! We got D’Angelico Guitars — they donated a guitar for us — so for every toy you bring you’re going to get a raffle ticket for winning the guitar. We’re going to give that away mid-show, so hopefully people bring a lot of toys! And then my friend Angie runs a company called Tufflicious Treats and they are amazing gourmet, hand-crated truffles. She’s donating $5 from every jar sold that night to Toys for Tots.

It’s going to be a really special, theatrical night.


Tickets for “A Very Merry Country Christmas” are on sale now. Seats run $25-$35, or for an extra $30 (separate purchase on her website) guests can also score a VIP package including access to set rehearsal and a pre-show meet-and-greet/photo op with the band.

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