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If love is a mysterious journey, why not celebrate with a little wanderlust together this Valentine's Day? Robin Catalano presents a collection of options that might expand the boundaries of romance just a touch; map courtesy OpenStreetMaps.
If love is a journey, why not celebrate with a little wanderlust together this Valentine's Day? Robin Catalano offers 17 options to expand the boundaries of romance just a touch; map courtesy OpenStreetMap.org.

Change of Heart: Offbeat Picks for Valentine’s Day Weekend

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. 

February 14

Decant with Plants—Gardiner, NY

The vegan gourmand’s dream: sample 4 wines and 1 sparkling selection alongside gourmet vegan cheeses and artisan chocolates.

The Villa at Saugerties—Saugerties, NY

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.

Hole up in the relaxed romance of the Mediterranean — without the jet-lag on Monday morning; photo courtesy The Villa at Saugerties.

Valentine’s Couples Massage Workshop—Woodstock, NY

“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. 

Valentine’s Day Jazz Party—Albany, NY

Swank it up with this upscale jazz party at the historic Ten Broeck Mansion. Food, champagne, live music, and dancing.

Date Night—Saratoga, NY

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.

Valentine’s Day Getaway—Troy, NY

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.

Super-Dark Valentine’s Day—Troy, NY

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.

February 15

Valentine’s Day Walk with Alpacas  

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.

You're just the cutest couple — everybody says so. Why not celebrate your love hanging out with perhaps the one animal who's own cuteness is at your level? You don't get to keep it, though.
You’re just the cutest couple — everybody says so. Why not celebrate your love hanging out with perhaps the one animal who’s own cuteness is at your level? You don’t get to keep it, though.

Cheese, Chocolate, and Spirit Pairing—Claverack, NY

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.


Aerial Valentine’s Day Partner Yoga—Albany, NY

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.

V-Day Dance Party—Albany, NY

Get your EDM and hip-hop fix with this dance party, courtesy of a trio of area DJs.

February 16

Bailey’s Third Annual Ice Bar—Saratoga Springs, NY

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.

Mr. Drag and Karl’s Phallic Times Valentine’s Show—Turners Falls, MA

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.”

February 17

Vegan Pop-Up Brunch with Berben & Wolff’s—Albany, NY

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.

Sunday Brunch at the Savoy—Albany, NY

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.

2nd Annual Hot Chocolate Festival—Olivebridge, NY

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.

You have heard that chocolate and love are neuro-chemical cousins, right? Well, add to that the chilly winter breezes and the thrill of sliding to get your heart pumping. Snuggle up!
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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.

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