Berkshire— The Berkshires offer a natural and cultural haven to visitors and residents alike, especially around the holidays. To bring light to a holiday season in dark times, after we’ve done everything that we could do, all we have left is defiant joy and celebrations of love: self love, romantic love, love of friends and family, love of community, and love of the arts and nature. This Valentine’s Day, I hope that you all find moments of joy and ways to celebrate love. In this spirit, I offer you this specially curated selection of Valentine’s Day events taking place in and around the Berkshires.
On Saturday, February 14th at 7 p.m., Hudson Hall in the the historic Hudson Opera House, located at 327 Warren Street in Hudson, N.Y., presents a Valentine’s Day Concert with two-time GRAMMY winner and 2026 nominee jazz vocalist Nicole Zuraitis. She will bring her soulful touch to timeless love songs and dazzling originals, including selections from her 2024 GRAMMY-winning album “How Love Begins.” Enjoy romantic ticket add-ons, such as Champagne and a sweetheart table for two.
On Saturday, February 14th at 7:30 p.m., Buttonball Barn, located at 17 Main Street in South Egremont, presents a special Valentine’s Day performance by The Wolff Sisters, an award-winning trio of hardworking musicians with a big, roots-driven sound grounded in American storytelling, the perfect soundtrack for a cozy winter night filled with soul, harmony, and heart.
On Friday, February 13th at 7 p.m., WANDER, located at 34 Depot Street in Pittsfield, presents the Misty Blues Love Jam, a Valentine’s celebration of love and the collective love of live music.
On Friday, February 13th at 7 p.m., the Mahaiwe Performing Arts Center, located at 14 Castle Street in Great Barrington, presents “Lovers & Strangers,” selected shorts with stars of stage and screen Jane Curtin, Lauren Ambrose, Sonia Manzano, and David Costabile. The popular radio show and podcast returns for an evening of romance and intrigue filled with funny, mysterious, and poignant short stories about love, desires, and unexpected encounters.
On February 13th and 14th at 7:30 p.m., after nearly 16 years of glitter, grit, and fearless creativity, Gypsy Layne Cabaret & Co. will present “Last Dance with Gypsy Layne,” its final performances, at Bennington Theater, located at 331 Main Street in Bennington, Vt. Marking the end of a beloved era, the Valentine’s Day performances mark the final shows ever for the inclusive troupe and will feature a specially curated program to serve as a final love letter and celebration of love, glitter, and gratitude for the audiences who made every shimmy, strut, and sparkle worthwhile.
On Saturday, February 14th beginning at 10 a.m., the Clark Art Institute, located at 225 South Street in Williamstown, will offer special activities in celebration of Valentine’s Day. From tender brushstrokes to flirtatious figures, visitors are welcome to visit the galleries to find all the forms of love. There will be a love-inspired gallery tour at 1 p.m. Write a note about the artwork that pulls at your heartstrings and share it on the “art lovers wall” and read the love letters left by others.
On Saturday, February 14th at 7 p.m., celebrate Valentine’s Day at the Crandell Theatre, located at 48 Main Street in Chatham, N.Y., with dinner and a movie. Watch “Dirty Dancing” on the big screen with a chicken or vegetarian boxed dinner catered by Hudson Meal Company. This romantic classic, starring Jennifer Grey and Patrick Swayze, pulsates with the energy of the salsa, ballroom, and ballet styles that Johnny teaches Baby in the wild, in the water, and in the studio. The Oscar-winning title song “(I’ve Had) The Time of My Life,” will have you sashaying down the aisles. The Crandell is also showing the romantic classics “The Princess Bride” at 1 p.m. and “The Notebook” at 4 p.m.
On Saturday, February 14th at 5 p.m., the Triplex Cinema, located at 70 Railroad Street in Great Barrington, continues its Screwball Valentine’s series with a screening of “Bridget Jones’ Diary,” Sharon Maguire’s modern update of “Pride and Prejudice” follows the single Bridget (Renée Zellweger) as she navigates a love triangle with the buttoned-up Mark Darcy (Colin Firth) and rakish Daniel Cleaver (Hugh Grant.)
On Saturday, February 14th at 7 p.m., the Mahaiwe Performing Arts Center, located at 14 Castle Street in Great Barrington, presents a special Valentine’s Day screening of “Moulin Rouge!” In a club called the Moulin Rouge, a once-in-a-lifetime romance develops between Christian, an English poet, and cabaret performer Satine.
On Friday, February 13th at 8 p.m., Berkshire Pride presents “TRULY MADLY 90’s,” a Valentine’s Day dance party for the LGBTQ+ community and allies at the Stationery Factory, located at 63 Flansburg Avenue in Dalton. Expect a night full of dancing, connection, and queer joy — plus drag performances from beloved Berkshire favorites. You’re invited to fall in love on the dance floor with DJ BFG spinning slow jams, pop divas, and all your favorite 90’s throwbacks. Come dressed in your best 90’s look, or don’t. Whether you’re rolling deep with friends, dancing solo, or showing up with your sweetheart, this is a space to be exactly who you are.
On Thursday, February 12th at 7 p.m., the Berkshire International Film Society’s BIFF Social Club presents the “Lonely Hearts” Valentine’s Day dance party at the Dr. Sax House, located at 35 Walker Street in Lenox. Get on the dance floor while DJ Ethical Drift keeps you moving with feel-good music and irresistible tunes, while favorite cult-classic films play in the background. Whether you’re single, taken, or somewhere in between, this is your excuse to get out, get dressed up, and dance. There will be a cash bar and plenty of nostalgic Valentine’s Day candy to enjoy all night.
On Thursday, February 12th at 7 p.m., Bottomless Bricks presents “Brick & Sip: Valentine’s Edition” at WANDER, located at 34 Depot Street in Pittsfield. Whether you come solo, with friends, or with that special someone, this feel-good evening is guaranteed to warm your heart. Build a LEGO “Cute Hamster” while enjoying handcrafted truffles from Truffles By Tarah and zero-proof beverages from WANDER’s thoughtfully curated menu.
On Thursday, February 12th at 6 p.m., “Paint Your Partner” with artist Mike Carty at Solarium, located at 46 West Street in Pittsfield. Bring your partner or whomever you’d like for a night of fun and creativity. There will be guidance, snacks, and beverages.
On Thursday, February 12th at 5 p.m., Mad Rose Gallery, located at 5916 North Elm Avenue in Millerton, N.Y., presents a Valentine’s Paint & Sip with artist Lainey Bye. Bring your lover, self, or a friend for a fantastic evening of painting, socializing, and sipping wine from Rosenthal Wine Merchant.
On Saturday, February 14th from 10 a.m. to 3 p.m., Ventfort Hall Gilded Age Mansion and Museum, located at 104 Walker Street in Lenox, presents vintage Valentine craft-making. Valentine greetings were a true art that flourished in the Gilded Age. Join Louise Levy for a special session of learning about and assembling your own custom vintage Valentine greetings and cards.
On Saturday, February 14th from 11 a.m. to 4 p.m., celebrate Valentine’s Day with a Jazz Age twist at the Norman Rockwell Museum, located at 9 Glendale Road in Stockbridge. Inspired by the “Jazz Age Illustration” exhibition, families will explore the lively style of the 1920s and create their own Valentine-themed artwork using printed images of flappers, musicians, and sweethearts.
Through February 12th, drop by the Berkshire Athenaeum, located at 1 Wendell Avenue in Pittsfield, to make Valentines for Veterans. Stop by any time the library is open to make a Valentine for a local Veteran. All card making supplies are provided.
On Saturday, February 14th at 11 a.m., the Eric Carle Museum of Picture Book Art, located at 125 West Bay Road in Amherst, presents a special story-time with award-winning author and photographer Shelley Rotner, as she shares her new picture book “Love is a Big Feeling.” Families will enjoy a reading, followed by book signing and an invitation to create their own Valentine’s Day cards.
On Saturday, February 14th at 7 p.m., Ventfort Hall Gilded Age Mansion and Museum, located at 104 Walker Street in Lenox, presents ”The Astrology of Love and Sex” with Chelsea Gaia. How do Venus, Mars, the Sun, and the Moon influence your relationships? Was it meant to be, or was it fated to end? How can the stars explain the one who got away? Find out at this playful presentation in the ambiance of a Gilded Age library. Enjoy a cash bar of bubbles and wine by Dare Bottleshop.
On Saturday, February 14th at 1:30 p.m., The Mount, located at 2 Plunkett Street in Lenox, presents Valentine’s Day Forest Bathing and Tai Chi with certified instructor Mary Hannah Parkman. Parkman believes these group sessions provide a place of ease, peace, and kindness for her students, as she offers them space to embark on the beauty of nature and float off to stroll the grounds, where strangers share kind words with one another, and couples embrace. Find sweetness as you calm your nervous system and cultivate harmony for yourself, your beloveds, and nature.
On Saturday, February 14th from 11 a.m. to 1 p.m., Berkshire HorseWorks, located at 101 Patton Road in Richmond, presents their fourth annual “Romance At The Ranch” for Valentine’s Day. You may remember your first kiss, but you will never forget your first kiss with a rescued pony, horse, or donkey! Visit the ranch for kissing booths and photos with the four-legged Valentine of your choice. Hot cocoa and cookies will be served.
For those of you not in the mood for romance, on Friday, February 13th at 7:30 p.m., The Foundry, located at 2 Harris Street in West Stockbridge, presents “The Anti-Valentines Show” with Tony Award-winning actress and singer Cady Huffman and jazz and Broadway bass player Mary Ann McSweeney. Combining voice with bass and whatever else strikes their fancy, the duo pirouettes from Peggy Lee to Jimi Hendrix, with a promise that nothing is off-limits, except romance. There will be no songs about romance.
On Friday, February 13th at 4 p.m., Ventfort Hall Gilded Age Mansion and Museum, located at 104 Walker Street in Lenox, is hosting a Galentine’s Day Tea. Gather your gals and pals to celebrate the love of friendship… and chocolate! Featuring the Red Velvet Cupcake Tea from the Republic of Teas with a magical assortment of themed goodies. Dress in the theme that best defines your friendship (Thelma & Louise? Golden Girls? Mrs. Roper?) and celebrate amongst friends.
On Sunday, February 15th at 4 p.m., “Paint Your Bestie” at Dottie’s Coffee Lounge, located at 444 North Street in Pittsfield. Celebrate Galentine’s Day by spending a fun afternoon with your best friend. Guided by local artist Diane Firtell, the event includes all materials, chocolate covered strawberries, and a cash bar.
On Thursday, February 19th at 7 p.m., Bennington Theater, located at 331 Main Street in Bennington, presents A Galentine’s Day “Parks & Rec” trivia night with Jim Thatch. This fundraiser supports the Take Care Project, which works to advance local menstrual and hygiene equity. Delicious refreshments will be available.
Let there be light!
