Visit Orange County, N.Y., for a Valentine’s Day Weekend Filled with Love, Laughter, Great Food – and Maybe a Little Mystery

 Orange County is the perfect Valentine’s Day destination, offering romantic dinners, Galentine’s brunches, food-and-wine pairings, a comedy show and even a Valentine’s-themed murder mystery — all just an hour from New York City. And this year, the celebration of love and romance falls on a Saturday, creating a long weekend with Presidents Day and turning Orange County into a mid-February “microcation” hotspot.

Orange County elevates Valentine’s Day with craft beverages, farm-fresh foods and natural settings. Take your special someone, or your besties, to relax at brunch high above the Hudson River, nibble on a chef’s delicacies paired with wines and even stay for a night or two. The region is an ideal destination to rest, relax and rejuvenate with the ease of a stress-free, multi-day escape an easy drive from home.

“With its fresh air, magnificent scenery and a warm, welcoming vibe, Orange County offers a Valentine’s weekend that’s romantic and memorable beyond your expectations,” said Amanda Dana, Director of Orange County Tourism & Film. “Our Valentine and Galentine festivities bring the fun, the food and the activities you’re looking for. While you’re here, keep the romance going with a longer stay in one of our fabulous accommodations.”

The places to stay include the cozy Cromwell Manor Inn in Cornwall, the elegant and historic Thayer Hotel adjacent to the U.S. Military Academy at West Point, the charming Stagecoach Inn in Goshen and a range of other inns, hotels and bed-and-breakfasts offering comfort, luxury and peace of mind.

Here are just some of the many Valentine’s Day-related events in Orange County, N.Y. A full list of events, celebrations and accommodations can be found at pickocny.com

Feb. 7, 11 a.m. – 2 p.m.

Galentine’s Brunch at Villa Venezia

Villa Venezia

2257 Goshen Turnpike, Middletown, N.Y.

Why it stands out: Leave the boys home for a girls’ day out with unlimited mimosas, music and a buffet menu that satisfies every craving, including fig prosciutto pizza, eggplant rollatini and sesame chicken.

Learn more: Galentine’s Brunch at Villa Venezia


Feb. 13, 6 p.m.

Chef and Winemaker Dinner Series: Romance and Reserve Wines

City Winery Hudson Valley

23 Factory St., Montgomery, N.Y.

Why it stands out: Immerse yourself in an exclusive evening as part of the Hudson Valley City Winery’s Chef and Winemaker Dinner Series. Executive Chef Tony Moustakas crafts a Valentine’s tasting menu paired with the winery’s varieties.

Learn more: Romance and Reserve Wines


Feb. 13, 8 p.m.

Valentine’s Day Comedy Night

Aspire Brewing

600 North Galleria Drive, Middletown, N.Y.

Why it stands out: A lineup of comedians brings big laughs while you enjoy fresh craft beer in a fun, relaxed atmosphere. Enjoy comedians including Vishnu Vaka, Nick Bailey, Gylije Veljic and Cam Stafford.

Learn more: Valentine’s Day Comedy Night


Feb. 13 and 14, 5 p.m. – midnight.

Valentine’s Day Dinner

The Thayer Hotel

674 Thayer Road, West Point, N.Y.

Why it stands out: Indulge in an intimate four-course dinner at MacArthur’s Riverview overlooking the Hudson River. Choices include pan-seared scallops, bronzed filet mignon and vegetable Wellington, capped off with decadent desserts. Stay overnight to complete the experience.

Learn more: Valentine’s Day Dinner


Feb. 14, 9 a.m. – 2 p.m.

Valentine’s Brunch at the Borland House

The Borland House

130 Clinton St., Montgomery, N.Y.

Why it stands out: Celebrate Valentine’s Day with brunch, bubbles and a little extra sweetness. Brunch features a breakfast tower, house-made favorites, pink drinks and optional flower bouquets for a finishing touch.

Learn more: Valentine’s Brunch at the Borland House


Feb. 14, 6 p.m.

Cupid is Stupid at the Switch Inn

The Switch Inn

126 E. Main St., Middletown, N.Y.

Why it stands out: Celebrate at a party for both singles and couples who share the motto, “We love love… but cupid is stupid.” Wear red and get a free drink (beer, wine or cocktail); DJ Mack spins tunes from 9 p.m. Champagne will be kept on ice all night.

Learn more: Cupid is Stupid


Feb. 14, 6 p.m. – 9 p.m.

Silver Dollar Saloon: A Valentine’s Murder Mystery

Blue Arrow Farm

86 Glenwood Road, Pine Island, N.Y.

Why it stands out: The farm’s newest murder mystery takes you to the wild, wild West. Inspired by Mark Twain’s humor, the adventure takes a deadly turn when an old prospector is murdered and his gold-mine deed disappears. Suddenly, every lovelorn gambler, desperado and gunslinger is a suspect. Tickets include a three-course buffet dinner.

Learn more: Silver Dollar Saloon: A Valentine’s Murder Mystery


Feb. 14 and 15, 11:30 a.m. – 5 p.m.

Love at First Sip: Valentine’s Weekend

Brotherhood, America’s Oldest Winery

100 Brotherhood Plaza Drive, Washingtonville, N.Y.

Why it stands out: History, wine and atmosphere combine with dessert, music, a photo booth and a little friendly competition. The day includes a tour and tasting, a flirty toast of bubbly, a guided walk through Brotherhood’s historic underground cellars and a tasting. Couples may participate in a series of games designed to test your teamwork – and your sense of humor. Afterward, dance and celebrate with host DJ Tom.

Learn more: Love at First Sip Valentine’s Weekend