Valentine’s Day Starts Early With Celebrations That Are Divine, Elegant, Fun and Funky

February 3, 2023 at 10:25 am
On Valentine’s Day – and the days beforehand – Orange County, N.Y., is the place to fall in love, rekindle that special feeling or celebrate self-love with elegant dinners, brunches, live music shows or a sip-and-paint evening.

ORANGE COUNTY, N.Y. (Feb. 2, 2023) – On Valentine’s Day – and the days beforehand – Orange County, N.Y., is the place to fall in love, rekindle that special feeling or celebrate self-love with elegant dinners, brunches, live music shows or a sip-and-paint evening.

With Valentine’s Day falling on a weekday, Tuesday, Feb. 14, the events begin the weekend before on Friday, Feb. 10, and continue through the big day.

“Every love is special in its own way, and Orange County, N.Y., has the perfect celebration for you!” said Amanda Dana, Director of Orange County Tourism & Film. “For every taste, we have the perfect place to dine, listen to music, sip wine, paint and more. Keep the fire burning by staying for a perfect romantic weekend in one of our charming bed and breakfasts or other fabulous accommodations!”

Here are some of the many Valentine’s Day-related events in Orange County, N.Y.:

Friday, Feb. 10

Funk Junkies Valentine’s Show, The Silk Factory, 299 Washington St., Newburgh, N.Y.: Founded by Newburgh native Rich Fracasse, the Funk Junkies have been “laying down the funk” throughout the tri-state area for a decade. The Funk Junkies play upstairs at 8:30 p.m.; Hollywood Herb plays downstairs starting at 7 p.m. Doors open at 6 p.m. Learn More.

Friday, Feb. 10; Saturday, Feb. 11; Tuesday, Feb. 14

Valentine’s Dinner, The Thayer Hotel, 674 Thayer Rd, West Point, N.Y.: Enjoy a romantic dinner for two in MacArthur’s Riverview Restaurant. To make the memories last, indulge in the Valentine’s Overnight Package, which includes the same five-course prix-fixe meal with a complimentary bottle of wine, plus luxurious accommodations for two. Dinner is 7 p.m. to 11 p.m. Learn More.

Saturday, Feb. 11

Annalyse & Ryan and Friends: Love Songs from the Valley, City Winery Hudson Valley, 23 Factory St., Montgomery, N.Y.: Hudson Valley Americana duo Annalyse & Ryan are joined by singer/songwriters Drew Angus and Jeremy Schonfeld for an intimate evening of Valentine’s themed music. The artists will present a songwriters’ round focused on love and all the things that come with it. Whether you’re celebrating a new love, years of commitment or your love of your independence, you’re in for a stellar night of songs and stories! Doors open 6 p.m., show starts 8 p.m. Learn More.

Sunday, Feb. 12

Galentine’s Brunch, the Venue at Winding Hills Golf Club, 1847 State Route 17K, Montgomery: Enjoy a delicious brunch while celebrating a more recent tradition, Galentine’s Day, when women get together to celebrate their friendships and connections. Brunch: 10 a.m. to 3 p.m.  Learn More.

Valentine’s Brunch with Live Music, Cove Castle Restaurant, 13 Castle Court, Greenwood Lake: Jazz upstairs with a view of Greenwood Lake creates perfect ambience for a Valentine’s weekend brunch. Brunch is 11:30 a.m. to 4 p.m., music is 1 p.m. to 3 p.m. Learn More.

Valentine’s Couples Sip & Paint, Divine Events Creators, 155 Main Street, Goshen, N.Y.:

Divine Events Creators present an evening of wine, dinner, painting, sweets and “all things delicious and divine.” It runs 4 p.m. to 7 p.m. Learn More.

Tuesday, Feb. 14

Sip, Paint, Love – A Bubbles Brushes Special Event, City Winery Hudson Valley, 23 Factory St., Montgomery: Love is in the air – and on the canvas. Vicki Andrade from ArtVicki Creations in Middletown will draw out your inner Picasso as you replicate her Valentine’s Day creation. Enjoy six special tastings matched with six light bites throughout the evening, with introductions by the winery’s experts. Starts at 6 p.m. Learn More.

About Orange County Tourism & Film

Orange County Tourism & Film, based in Goshen, N.Y., is the county’s tourism and film production headquarters and a participant in the I LOVE NY program. A comprehensive listing of area attractions, lodging, events and film resources can be found at Additionally, a fun, free, 56-page travel guide is available for digital download at

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