Winter in the Berkshires is far from dull and dreary—and our local businesses and arts venues know how to make a holiday extra special. As your area experts, we’ve picked a few of our favorite things to do near our offices in West Stockbridge and Great Barrington over Valentine’s Day weekend. No matter your relationship status, there are plenty of ways to get out and celebrate the love in your life!
1. Romantic Dining: Best Restaurants in Great Barrington & West Stockbridge
If the pressure is on to pick the perfect eatery for your Valentine, we have good news: it’s hard to find a bad meal in Southern Berkshire County. But for a special night, we’ve picked some standouts in ambiance and truly tasty dishes. Valentine’s is a busy night for our local hotspots, so it’s always best to call ahead and see if your destination takes reservations!
Romantic restaurants in and near West Stockbridge
-
AMICI: With a beautiful outdoor space in the summer months and an equally stunning dining room open year-round, AMICI is a classic go-to in West Stockbridge. Their menu focuses on comforting food and a Southern Italian spirit, with an emphasis on sourcing ingredients from right here in the Berkshires.
-
Acqua al 2: This Italian eatery opened in late 2024 and has quickly become a local favorite. Named after its original address in Florence, it has expanded to locations in San Diego, Washington, D.C., and Annapolis. Despite its Florentine beginnings, Acqua al 2 curates its menu to offer tastes from regions all over Italy.
-
Once Upon a Table: In nearby Stockbridge, locals frequent Once Upon a Table (celebrating 30 years in 2026!) to try new dishes from their ever-changing menu. The restaurant’s ethos centers on utilizing seasonal ingredients. Reservations are highly recommended, as this powerhouse operates out of a tiny space!
Romantic restaurants in downtown Great Barrington
-
Bizen Gourmet Japanese Restaurant: Locals make an entire evening out of dining at Bizen. Inside, you’ll find a blend of Japanese and American cultures reflected in the decor and seating. Their expansive menu is famous for high-quality, creatively named sushi rolls.
-
The Elm: Located nearly across Railroad Street from Bizen, The Elm specializes in modern New England cuisine within a stylish, upscale dining space. For a more casual atmosphere, The Elm owns the attached Uva Pizza, which returns from winter break at the end of January.
-
Number Ten: If splitting a ribeye is your idea of romance, look no further than 10 Castle Street. It makes for a perfect dinner-and-a-show companion to The Mahaiwe next door and is famous for its quality cuts and expansive whiskey selection.
2. West Stockbridge Nightlife: The Anti-Valentine’s Show at The Foundry
We are proud supporters of The Foundry, located just around the corner from our West Stockbridge office. On Friday, February 13, they are offering refuge for the jaded with an outstanding jazz show featuring a strict "no love songs" setlist policy. “The Anti-Valentines Show” stars Tony-winning actress and singer Cady Huffman alongside Mary Ann McSweeney—a Broadway bassist and Stone House agent!
3. Lenox Social Events: Lonely Hearts with BIFF at Doctor Sax House
While the Berkshire International Film Festival (BIFF) typically makes Great Barrington its home each summer, they are launching new ways to bring incredible events to the area all year long. The latest is the Lonely Hearts Dance Party in nearby Lenox on Thursday, February 12. Whether you are single, in a relationship, or on the “it’s complicated” spectrum, BIFF invites you to Doctor Sax House for candy, dancing, and a cult-classic film. The event is hosted by the BIFF Social Club, a committee that connects young professionals over a shared love of film and the local community.
4. Valentine’s Treats at Chocolate Springs Cafe in Lenox, MA
What is Valentine’s Day without chocolate? Chocolate Springs Cafe’s creations are as delicious as they are beautiful. Their storefront includes cozy seating for sipping on hot chocolate or a specialty coffee made with shaved chocolate. Whether you visit with friends or a date, Chocolate Springs is a "blink-and-you’ll-miss-it" treasure that makes this area special.
5. Gilded Age Romance: Valentine’s Weekend at Ventfort Hall
Ventfort Hall has a variety of engaging programming in February before their temporary spring closure. This mansion-turned-museum is still undergoing renovation, offering new ways to engage with this Lenox staple.
-
Friday, February 13 - Galentine Tea: Ventfort Hall’s celebration of female friendship comes in the form of Red Velvet Cupcake Tea, served with plenty of chocolate and other treats. The museum invites you to “dress in the theme that best defines your friendship” when you come with your gal pals. .
-
Saturday, February 14 - Vintage Valentine Craft Hour: The best gifts come from the heart. All ages are welcome to create your own vintage-inspired card, offered at no additional cost with your self-guided tour ticket.
-
Saturday, February 14 - The Astrology of Love and Sex: In the evening, the museum hosts a saucier cabaret-style show with Astrology and Tarot guide Chelsea Gaia. The evening is part lecture, part audience participation, complete with a wine bar to boot.
6. Winter Activities: Neon Nights & Glow Dance Party at Catamount Ski
Romance isn't the only way to get your blood pumping; you can spend Saturday, February 14, skiing and snowboarding at Catamount Ski Resort with your loved ones of all types. Night skiing ends early for a special free dance party starting at 6 p.m. outside the lodge, followed by a laser show at approximately 8:15 p.m.
7. Berkshire Wellness Retreats: Miraval and Kripalu Programs
The winter season is a great time for a “stay-cation" at some of the area’s world-class resorts–the Kripalu Center for Yoga & Health even offers winter discounts to attract yogis during the colder months. Both Miraval and Kripalu are offering special programs for couples over Valentine’s weekend–but also continue to offer their standard rest, relaxation and wellness opportunities at the same time. Both institutions offer overnight experiences, or daytime programming–perfect for a quick getaway with friends, or to give yourself some much-needed self care.
Berkshire Lifestyle & Real Estate: Frequently Asked Questions
What is the best town for a second home in Southern Berkshire County?
While "the best" depends on your lifestyle, Great Barrington and West Stockbridge—home to our two Massachusetts offices—are frequently top choices. Great Barrington offers a vibrant, walkable downtown, while West Stockbridge provides a serene, artistic village atmosphere with easy access to the New York border and the Mass Pike. For privacy, towns like Alford and Egremont offer stunning rural landscapes.
We often work with buyers who are struggling to pick Massachusetts or New York as their getaway from New York City or Boston. Read our guide on the best border towns here.
What are the top cultural events in Great Barrington during the winter?
Beyond the summer season, Great Barrington remains a cultural anchor. The Mahaiwe Performing Arts Center hosts year-round concerts, HD broadcasts of the Met Opera, and classic films. Saint James Place is a hub for chamber music and community lectures, and the Berkshire South Regional Community Center offers seasonal events like family dance parties and wellness workshops that keep the community connected during the colder months.
What are the best options for downsizing in Southern Berkshire County?
There are lots of great reasons to downsize in Berkshire County. Many homeowners in the Berkshires are choosing to transition from large historic estates to luxury condos or smaller, single-level village homes in areas like Lenox or Lee. This allows residents to remain close to cultural staples like Tanglewood and the Mahaiwe while reducing maintenance. Our team is happy to work with you to find the perfect home for your budget and lifestyle in this upcoming chapter.
How do I prepare my Berkshire home for sale?
You don’t need a major remodel to make a powerful impression. A Stone House agent can provide specific recommendations to make your home look its best. In the meantime, read our general guide on Seven Essential Things To Do Before Listing Your Home for Sale.
