As Snoopy sage Charles M. Schultz once pointed out, “All you need is love. But a little chocolate now and then doesn’t hurt.” And if we had to venture a guess, we’d bet your plus-one would also appreciate a night (or day, or weekend) away for Valentine’s Day. Use this roundup of the most promising picks within driving distance of the Berkshires, and try something new, fun, provocative, or off the beaten path—and, we hope, more than just a little romantic.
The vegan gourmand’s dream: sample 4 wines and 1 sparkling selection alongside gourmet vegan cheeses and artisan chocolates.
For the full-on romantic experience, drop the kids off with their grandparents and head to the Catskills. The Villa at Saugerties is a light-filled, Mediterranean-style boutique B&B that offers the ultimate laid-back-luxe getaway. Each queen or king room features organic linens, a gas fireplace, Moroccan-tiled bathrooms (some with soaking tubs), complimentary in-room drinks, Netflix, WiFi, and a breakfast feast. Ask about the four-course prix fixe Saturday dinner. Special winter rates through March.
“In this high-tech, low-touch world,” the event description says, “we all need to learn to slow down and really appreciate our life partner.” There’s no better way than to get touchy-feely with this DIY couples’ massage.
Swank it up with this upscale jazz party at the historic Ten Broeck Mansion. Food, champagne, live music, and dancing.
For a lower-key Valentine’s in a pretty, winter wonderland setting, head to the popular Salt & Char in Saratoga Springs for their two-fer of sides, desserts, and a bottle of wine.
Because why go white tablecloth and smooth jazz when you can play shuffleboard, bocce ball, and board games? Don’t forget the $5 margaritas, including a Strawberry Champagne Margarita.
Sure, it’s a dance party, and there are others around the region. But how many boast a mix of Americana folk-pop, surf rock, and synth-pop/“horror soul”?
Love: The Way You Laugh—Florence, MA
Cocktails, a buffet, and, most likely, some merciless mocking of America’s favorite commercial holiday. Comedians include Kim “Boney” DeShields, Tim Lovett, Andre Kim Jr., Sarah Martin, and Dale Cover.
Nothing says “I love you, but your Whitman’s Sampler isn’t cutting it” quite like an outdoor stroll with adorably fluffy, cud-chewing friends. From February 14 to 17, Lilymoore Farm is hosting couples’ walks with their resident alpacas. You’ll also take home a photo, frame, and alpaca key chain to commemorate your walk.
Wine, schmine. By the weekend, we’re ready for the hard stuff. Luckily, Olde York Farm, maker of fine artisan spirits, is obliging us. They also have an on-site airbnb, so you can get sozzled responsibly.
Indulge your inner Cirque du Soleil contortionist at this very special aerial yoga class for two (invite “a spouse, a friend, a first date,” the event description helpfully notes). Who cares if you’re coordinated? This one checks two boxes: trying something new, and getting a great laugh.
Get your EDM and hip-hop fix with this dance party, courtesy of a trio of area DJs.
Bailey’s signature winter event features ice sculptures, ice tables, and—you guessed it—an ice bar with shot glasses made of ice, sent careening down an ice luge. With hot chocolate cocktails and all-night drink specials, you won’t even feel the chill.
Head to the Shea Theater for this adults-only cabaret and pop-up shop, and be transported to a “seedy little spot, where the gin is cold and the piano is hot.”
Soak up the last of your love hangover with this all-vegan brunch at the Hollow Bar + Kitchen, Albany’s go-to spot for unusual special events and live performances.
For a more traditional take on Valentine’s brunch, kick back at fine-dining restaurant the Savoy Taproom, with food, cocktails, and Build Your Own Bloody Marys.
A sweeter take on Valentine’s, this festival features hikes and sledding, plus indoor crafts, lunch, and multiple versions of the perennial favorite toasty treat.
Robin Catalano believes in the power of storytelling to connect communities and cultures. She’s applied her creative approach to writing for magazines, books, blogs, websites, and a wide variety of marketing projects, and has published more than 75 articles and 1,000+ blog posts. As an editor, she has worked on more than 350 books for publishers including Penguin Random House, Workman, and Simon & Schuster. She has also served as a book coach for independent authors, helping them take their ideas from concept to print. An avid traveler and travel writer, Robin lives, reads, and writes voraciously in upstate NY.