Looking for the perfect way to celebrate love this Valentine’s Day? Whether it’s music, food, or just some good old-fashioned romance, there’s something for everyone—because let’s be honest, we could all use a little more love!
Wednesday, Feb. 12
28th Annual Chocolate Fest. 3:30 p.m. at the Kent Center School Cafeteria (9 Judd Ave., Kent). Proceeds benefit the Kent Center School Scholarship Fund. Fill a plate for $5 with delicious chocolate creations. Email for more info: info@kcssf.org.
Thursday, Feb. 13 & Saturday, Feb. 15
Fleece Pillow Making Workshop at David M. Hunt Library (63 Main St., Falls Village) The DM Hunt Library is making heart pillows to give to seniors for ‘Random Acts of Kindness’ Week! Workshops will be held Thursday, Feb. 13 from 5 to 7 p.m. or Saturday, Feb. 15 from 10:30 a.m. to 12:30 p.m. Learn to make knot-tie, no-sew pillows for local seniors. Use donated fabric and patterns or bring your own.
Thursday, Feb. 13
Senior Sweetheart Supper at Sharon Hospital (50 Hospital Hill Rd., Sharon) 3:45-5:0 p.m.– buffet dinner. 5 to 5:30 p.m. – Guest speaker Sheri Harrison, MD. Dr. Harrison is a general cardiologist, board-certified in Internal Medicine and Cardiovascular disease by the American Board of Internal Medicine. For reservations: contact Rebecca Moreira at Rebecca.Moreira@nuvancehealth.org or call (860)364-4237
Friday, Feb. 14
Friendship Bracelets at NorthEast-Millerton Library (75 Main St., Millerton) 3 to 4 p.m. It isn’t too late to make a last-minute Valentine present for a friend! Make bracelets with beads and/or embroidery thread. No experience necessary. All are welcome.
Friday, Feb. 14
Valentine’s Day Screening of Classic Romantic Film, “Roman Holiday” at The Triplex Cinema (70 Railroad St., Great Barrington)at 5 p.m. Starring Audrey Hepburn and Gregory Peck, this beloved romantic comedy won three Academy Awards and was shot on location in Rome. Directed by William Wyler, the film is a timeless classic. Tickets at thetriplex.org.
Friday, Feb. 14
A Steamship Feast at Stissing House (7801 S. Main St., Pine Plains)Arrive between 6:30-7 pm; dinner starts at 7. No vegetarian, vegan, or pescatarian options. Note allergies in your reservation or email feasts@stissinghouse.com. Enjoy snacks and drinks in the upstairs bar, followed by a long-table feast in The Barn with cocktails, punch, wine, and dessert.
Tickets are for two; email feasts@stissinghouse.com for group seating requests.
Friday, Feb. 14
Valentine’s Day Dinner Party at Ward’s Nursery (600 Main St., Great Barrington) After Hours, a new aged, community-centric outfit is hosting a Valentine’s Dinner at Ward’s Nursery. There will be a cozy, 7-course vegetable-forward feast served family-style in the greenhouse. Enjoy a cocktail hour, live music by Glori Wilder, and a vibrant winter escape! Reservations: www.afterhoursgb.com
Friday, Feb. 14
Valentine’s Day Dinner & Dance at Coe Park Civic Center (101 Litchfield St., Torrington) 5:30 to 7:30 p.m.Located at the Coe Park Civic Center, the Recreation Department is hosting a fun night of music and food for couples or friends. A buffet style dinner from Jimmy’s Store with desserts will be included in the price. Sequel, a fun jam band , will be playing music from all decades to get you in the right mood to sway your hips, clap your hands, and sing along. Reservations: (860)489-2274
Friday, Feb. 14
Jungle Love Dance Party at Stissing Center (2950 Church St., Pine Plains) at 7 p.m. Voted Best Band & Best Party Band in the Hudson Valley, Jungle Love is more than a band—it’s an experience. Fronted by award-winning singer Cher, this powerhouse group features musicians who’ve played with legends like The Isley Brothers, Aretha Franklin, and Ben E. King. Get ready for a high-energy journey through the best of Classic Soul, R&B, Motown, Disco, and Funk. This event is FREE.
Saturday Feb. 15
Love Letters at Sharon Playhouse (49 Amenia Rd., Sharon) at 7 p.m. Sharon Playhouse presents a special benefit reading of Love Letters by A.R. Gurney, starring Gretchen Mol (Boardwalk Empire) and Campbell Scott (House of Cards), directed by Artistic Director Carl Andress. Experience this intimate, one-night-only event exploring love and connection. Proceeds support the Playhouse’s arts and education programs. Tickets: sharonplayhouse.org/love-letters
Saturday, Feb. 15
A Midwinter’s Night in the Village at David M. Hunt Library (63 Main St., Falls Village) from 6 to 8 p.m. Enjoy an evening of homemade breads, chocolate treats, poetry, and songs celebrating love. Live music by Galactic Overtones, plus wine, beer, and non-alcoholic drinks included. huntlibrary.org/midwinter | 860-824-7424
- In a world that could always use more love, here’s your chance to spread it—whether through music, food, laughter, or sweet treats. Enjoy!
