ELEVEN DATE IDEAS TO WARM UP YOUR WINTER
By Taylor Staubach
Holiday 24
Although winter for many is a time of self-reflection and solitude, it can be the perfect opportunity to enjoy all that the Berkshires has to offer with your partner. Now is the time to turn up the heat and stay warm by enjoying the cozy and rejuvenating experiences the season brings. Whether you and your partner prefer the quiet serenity of a candlelit yoga class or the crisp thrill of snow-white slopes, the Berkshires has an array of date opportunities to suit any pair. We’ve compiled a list of outing ideas designed to keep the flames of love burning strong all winter long.
Stay-Cay Getaway
Longing to be pampered? For a day of complete relaxation and rejuvenation, head to Miraval Berkshires in Lenox, where guests can handpick from a variety of complimentary activities all aimed at creating a “life in balance,” including luxurious amenities at the spa of the same name. Afterwards, indulge in a gourmet lunch at Harvest Moon Restaurant at Miraval, with options to extend your stay for dinner at 1894 for an additional cost. Included with the day package is a $220 resort credit per person, which can be used toward private sessions, fee-based activities like equine and culinary experiences, or additional spa services. Enjoy unlimited access to complimentary yoga, meditation, and fitness classes, plus full access to Miraval’s extensive resort amenities.
For a nearby outing, stroll through downtown Lenox and make sure to stop for a drink or bite to eat at Brava or sister restaurant Ombra. Offering tapas-style food, handmade pizzas, and cheese and charcuterie plates, Brava is the go-to place for a light meal, a full dinner, or an after-show snack. Brava boasts an impressive selection of craft beers, a multiple-award winning wine list, and killer craft cocktails. Ombra also has wide selection of drinks and a kitchen serving delicious bites till midnight.
Miraval, 55 Lee Rd., Lenox; miravalresorts.com
Brava, 65 Church St., Lenox; bravalenox.com
Ombra, 27 Housatonic St., Lenox; ombralenox.com
Keep it Casual & Classic
For a more laid-back but intimate date night, catch a film and an aperitif at the newly opened Images Lounge, adjacent to the long-standing community movie theater. Open daily from 4 to 8 p.m., the Lounge offers a selection of ready to drink cocktails and mocktails, as well as local beers, ciders, and wines. A full menu of curated cocktails and local spirits, inspired by favorite films, is available during bartender hours, Fridays and Saturdays from 6 to 11 p.m. It’s the perfect place to unwind before or after a show, or even as the feature itself. Images Lounge also hosts movie nights and community events. Want to really impress your cinemate? Ask about renting the space for a private screening. It worked for Tom Hanks in You’ve Got Mail!
Images Cinema and Lounge, 50 Spring St., Williamstown; imagescinema.org;
If you find yourself in south county looking for the perfect spot to catch a flick, The Triplex Cinema in Great Barrington offers an ideal blend of indie films, blockbusters, and documentaries. The holiday movie season kicks off November 22, with Oscar contenders and blockbusters hitting the screens. Also, keep a lookout for special engagements, such as the next generation of movie mavericks premiering their work at our Young Filmmakers Festival on November 16; and director Zia Anger makes a visit to The Triplex to discuss her new movie, My First Film, on November 21. Major releases will continue through the holidays, including James Mangold’s Bob Dylan biopic A Complete Unknown, which will have an talkback with local “Dylanologists” during Christmas week. This local theater is a community gem, known for its relaxed vibe and diverse lineup, making it a great choice for a laid-back escape. After the credits roll, step next door to Juju’s for a post-movie treat. The newcomer on the scene, Juju’s serves up a “quick-service” menu filled with more than just their famous fried chicken and soft serve.
The Triplex Cinema and Juju’s, 70 Railroad St., Great Barrington; the triplex.org;
Off the Beaten Path
Couples who crave the road less traveled should head to Canterbury Farm in Becket, where you can make the most of a snowy afternoon. Groomed cross-country ski and snowshoes trails wind through 200 acres of serene woodlands. Rent equipment for a full day of skiing, snowshoeing, or even ice skating, as you explore the historic farm, which dates back to 1780. Warm up with a hot chocolate at the recently opened ski chalet, also on the grounds.
For a delicious start to your day or an après-adventure bite, stop by The Neon Newt at the former Becket General Store. Open Thursday to Sunday, the breakfast and lunch counter is perfect for a quick bite before you hit the trails or pick up sandwiches to enjoy later. Looking to take a load off? Consider visiting on a Thursday evening for burger night, or go rogue on Monday, where dinner is an ever-changing menu of locally-sourced items.
Canterbury Farms, 1986 Fred Snow Rd., Becket; canterbury-farms.com
The Neon Newt, 30 Washington St., Becket; @neonnewt on Instagram
North County Museum Crawl
Looking to impress while keeping it light and conversational? A gallery crawl of a trifecta of museums in north county is sure to do the trick! Begin your excursion at the Clark Art Institute in Williamstown, where classic masterpieces by Renoir and Degas inspire conversation. Also, there are plenty of special events on the calendar. Check out the Clark + Images Cinema Movie Series: New Hollywood Auteurs held on Thursday evenings at the Clark’s Auditorium, beginning December 5 with Bonnie and Clyde. Other movies include The Godfather on December 19, Young Frankenstein on January 30, and more. Next, make a stop at Williams College Museum of Art (WCMA), where free admission gives you access to over 15,000 works of art. (Try to time it for the third Thursday of the month for WCMA at Night, an evening series of happenings with music, food, dancing, and more from 5 to 9 p.m.) Conclude with the contemporary at MASS MoCA in North Adams, where off-beat art installations are rich fodder for creating connection. After a full day of absorbing art, recharge over the ever-changing menu at Casita Berkshires, found on the MASS MoCA campus. A newer addition to the museum’s dining options, Casita brings authentic Latin flavors to your post-museum plans.
Clark Art Institute, 225 South St., Williamstown; clarkart.edu
WCMA, 15 Lawrence Hall Dr., Williamstown; art museum.williams.edu
MASS MoCA, 1040 Mass MoCA Way, North Adams; massmoca.org
Casita Berkshires, 1111 Mass MoCA Way, North Adams; casitaberkshires.com
Parent Picassos & Crafty Companions
If you’re done observing and want to get in on the action, Berkshire Art Center (BAC) is the date for you. With two locations, one in Stockbridge and the other conveniently located in central Pittsfield, BAC offers creative workshops perfect for couples looking to get their hands dirty. From pottery classes to painting sessions, it’s a fun way to spend an evening creating something together. BAC also offers customized private lessons for a tailor-made art experience. At the Stockbridge location, parents in need of a night out can enjoy free childcare through a partnership with Community Health Partners, on the second Friday of each month. After admiring your newest masterpiece, head to District Kitchen & Bar in Pittsfield, where innovative dishes are served in an intimate space, ideal for a satisfying rounding out of an evening. In Stockbridge, make a reservation at Once Upon a Table, an intimate dining experience where every plate is a work of art.
BAC, 13 Willard Hill Rd., Stockbridge, and 141 North St., Pittsfield; berkshireartcenter.org
District Kitchen & Bar, 40 West St., Pittsfield; district.kitchen
Once Upon a Table, 36 Main St., Stockbridge; onceuponatablestockbridge.com
More Hands-On Date Options
Township Four, located in the Red Lion Inn, is a gem of a store in so many ways. Peruse the eclectic selection of home goods and clothing and stay a while longer to take one of its many classes to create a centerpiece, a wreath, a terrarium, and a kokedama (Japanese art of growing plants). It’s a short stroll to grab a bite or a drink before or after a class at the Red Lion Inn, which offers three wintertime options. There’s the historic Main Dining Room, an ideal place to spend a romantic evening or mark a special occasion; the cozy and rustic Widow Bingham’s Tavern; and the lively Lion’s Den, with food, cocktails, and live music.
Another location where you and your mate can apply your creative botanical skills is The Plant Connector, located in both Pittsfield and North Adams. The neighborhood plant and lifestyle shop hosts festive workshops like wreath-making and intro to airplant mounting. It’s the perfect chance for you and your date to design your own botanical pieces. The verdant environment makes it an ideal spot to connect with nature and each other.
Post-workshop in Pittsfield, head over to 101 Restaurant and Bar for a Southern-inspired twist on modern American cuisine. Located on the second floor of the Holiday Inn, this spot offers a relaxed, yet chic atmosphere with elevated comfort dishes like hush puppies, fried green tomatoes, and gumbo. Whether you’re craving comfort food or a creative cocktail, it’s an ideal stop to unwind after your plant-making adventure.
If you’re visiting North Adams, follow up your plant-apalooza with drinks at 413 Bistro & Taproom, located inside Hotel Downstreet. Offering small snacks, slider and beer flights, and plenty of dishes to share, it’s the perfect location to cap off your creative night out. And if you’re in the mood for a short scenic drive, Coyote Flaco in Williamstown offers another option. Just over the mountain, this hidden gem serves up flavorful Mexican fare in an intimate setting. Warm up over a plate of their sizzling fajitas or sip on a refreshing mojito, making it a memorable way to round off your evening.
Township Four, 30 Main St., Stockbridge, townshipfour.com
The Plant Connector, 105 North St., Pittsfield and 73 Main St., North Adams; theplantconnector.com
Red Lion Inn’s Main Dining Room, Lion’s Den, and Widow Bingham’s Tavern, 30 Main St., Stockbridge, redlioninn.com/dining
101 Restaurant and Bar, 1 West St., Pittsfield; 101pittsfield.com
413 Bistro and Tap Room, 40 Main St., North Adams; 413bistro.com
Coyote Flaco, 505 Cold Spring Rd., Williamstown; on Facebook
Ice Breakers and Star Chasers
For a truly out-of-the-box date, start with an evening of curling with Curl Berkshires. This winter sport, often seen in the Olympics, offers a fun and active way to bond or break the ice while learning something new. Offering Learn to Curl sessions at the Boys & Girls Club of the Berkshires during the winter months, Curl Club members provide the equipment, teach you the basics and then you’re off–playing the coolest game on ice. Just looking to hit the ice? Public skate dates are offered throughout the winter with ice skates available to rent for $5 a session. Dates are posted on the BGC website and social media. Celebrate your victory (or mourn your loss) over a beer at Hot Plate Brewing Co., just two blocks away.
Curl Berkshires and Boys & Girls Club, 16 Melville St., Pittsfield; curlberkshires.org;
Hot Plate Brewing Co., 1 School St., Pittsfield; hotplatebeer.com
For a night equally eclectic, enjoy an enchanted evening under the stars (indoors!) at Hopkins Observatory, the oldest observatory in the U.S. There, you can marvel at the stars and explore the wonders of the night sky, while keeping warm. With regular planetarium shows on Friday evenings during the school semester, couples can enjoy a captivating presentation, guided by student volunteers. After your celestial adventure, continue your night out inside The Barn Kitchen & Bar at The Williams Inn, a beloved local gem known for its romantic atmosphere. Designed with privacy in mind, the dining room ensures that every table feels intimate and secluded, allowing you to savor each dish and enjoy your time together. Each month, The Barn offers a unique Chef’s Dining Series where couples can indulge in specially curated multi-course meals.
Hopkins Observatory, 103 Spring St., Williamstown: astronomy.williams.edu
The Barn Kitchen & Bar, 103 Spring St., Williamstown; thebarnwilliamstown.com
Ski & Après Ski
For couples who love hitting the slopes, you can’t go wrong with Jiminy Peak in Hancock, the largest ski and snowboard resort in southern New England, known for its snow-making capabilities. After an adrenaline-filled afternoon, ditch the slopes for craft cocktails (mocktails too!) and comfort food at Bluebird & Co., where cozy booths make for a perfect après ski setting. Check social media for music bingo, DJ dance parties, and special events!
Jiminy Peak, 37 Corey Rd., Hancock; jiminypeak.com
Bluebird & Co., 137 Brodie Mountain Rd., Hancock; eatatbluebird.com
Seeking a quieter experience? Head to the peaceful cross-country trails at Notchview in Windsor. With over 25 miles of ski trails, it’s easy to see why Notchview is a renowned winter destination. They even have a separate trail system for “skijoring,” or skiing with dogs! Follow it up with a hot drink and fresh-baked treats at the Old Creamery Co-op, a cozy cafè and market that’s perfect for relaxing after a bracing day outdoors. Grab a window seat, a mug of hot mulled cider, and a slice of homemade cake to share.
Notchview, 83 Old Rte. 9, Windsor; thetrustees.org/place/notchview
Old Creamery Co-op, 445 Berkshire Trail, Cummington; oldcreamery.coop
Vinyasa and Vino
Slow down and savor the moment with a romantic candlelit yoga session at Berkshire Yoga Dance & Fitness in Pittsfield. The gentle flow and soft glow help set the tone for a calming evening. Or immerse yourselves in the soothing resonance of a Healing Sound Bath, held weekly, designed to release tension and foster inner peace. Unwind together during a Yin & Restore class, focusing on long-held, gentle stretches perfect for leaving you refreshed, relaxed and connected. After your session, indulge in an intimate dinner at Sibaritas, around the corner at their new location on McKay Street. Known for their sophisticated take on Italian cuisine, it’s a date night that blends relaxation with culinary delight.
Berkshire Yoga Dance & Fitness, 55 North St., No. 201, Pittsfield; berkshireyogadancefitness.com
Sibaritas, 27 McKay St., Pittsfield; sibaritascafe.com
Sereni-Tea Seekers
Picture you and your partner unwinding together with a warm soak in a large outdoor hot tub, surrounding by the beauty of a snow-drenched Green River. Followed up with a relaxing couple's massage by the skilled therapists at InTouch Massage in Williamstown. Freshly rejuvenated, take a leisurely stroll to Tea and Boba Lounge located on Spring Street, just a short walk away. Here, you can craft your own delightful boba drink or choose from a menu brimming with over 45 organic teas, steeped to order. Whether you opt for a creamy matcha latte or a Vietnamese coffee, the ambience of real vinyl records playing a familiar tune and board games to play, invites you to relax and connect. With special events like Learn & Play Chinese Mahjong, Ramen Night, and Sunday High Tea, you’ll find it effortless to take your date to the next level. Don’t forget to meet Mango, the lounge’s adorable axolotl!
InTouch Massage, 84 Water St., Williamstown; intouchdayspa.com
Tea and Boba Lounge, 76 Spring St., Williamstown; teaandbobalounge.com
A Lively Night Out
If you’re craving a fiery evening of live entertainment, head to The Foundry in West Stockbridge. This buzzing venue brings an eclectic mix of performances, from soulful tunes to toe-tapping folk, as well as plays, poetry, comedy and more. It’s the kind of place where every seat is the best seat in the house.
Keep the good times rolling at Amici, just a short stroll away. Warm up with a comforting Italian dish in an inviting atmosphere, the perfect spot to savor wood-fired pizza or a generous bowl of pasta. Whether you’re raising a glass of vino or enjoying an espresso, this combination will ensure the night continues to hit all the right notes.
If you’re in the mood for something new, head over to Acqua Al 2, recently opened in the former Rouge space. This chic new addition to West Stockbridge is quickly gaining notoriety for a memorable dining experience in a refined yet inviting setting. For a more rustic atmosphere but still high-end option, Heirloom Lodge offers a warm, lodge-style atmosphere with an emphasis on fine dining and wine. Known for its farm-to-table philosophy, Heirloom delivers a locally sourced menu with standout dishes like their Heirloom rotisserie chicken for two, complete with roasted garlic bread pudding and drip-pan onions. With both prix fixe and à la carte options, it's the ideal place to enjoy a luxurious meal in a natural setting.
The Foundry, 2 Harris St., West Stockbridge; thefoundryws.com
Amici, 5 Albany Rd., West Stockbridge; on Facebook
Acqua Al 2, 3 Center St., West Stockbridge; acquaal2berkshires.com
Heirloom Lodge, 75 Pixely Hill Rd., West Stockbridge; heirloom lodge.com
As the days grow shorter, it’s easy to retreat into the warmth of home, but the Berkshires is brimming with winter experiences that call couples to step outside and reconnect. Whether you’re seeking adventure, relaxation, or a new way to explore the dense cultural landscape, these date ideas offer something for everyone. From intimate dinners to nights spent stargazing, the possibilities to spark romance and burn memories are endless. Winter is a season not just for rest, but of shared excitement and mutual warmth.