Whether the goal is to impress a special someone, or to simply dine in style, here are our picks for a unique and enchanting dining experience while in the Berkshires.
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Cantina 229
229 Hartsville-New Marlborough Road, New Marlborough, Massachusetts 01230We like to say that the dining experience at Cantina 229 actually precedes your arrival at the restaurant. Making your way past Great Barrington and into rural New Marlborough, first timers may be surprised to land upon this lively dining destination seemingly in the midst of nowhere. When parking in the first lot, small walkway lights guide patrons past a farmhouse, and if you’re lucky, avail a chance encounter with the resident hens. The amber glow of lights through Cantina’s ceiling-to-floor windows are truly inviting and inspire the appetite for some seriously inventive international fare. This airy barn-turned-restaurant is as one-with-nature as the ingredients of it’s homegrown and locally sourced menu items. What started as simply a once a week “Taco night” for restaurateurs Josh Irwin & Emily Rachel, Cantina now offers a full menu ranging from small “bites” to full portioned dinners. Never fear, Taco Tuesdays hasn’t gone anywhere- a revolving menu of specialty tacos are available each Tuesday night, year round. The open kitchen, post & beam architecture and lively vibe make Cantina 229 an obvious choice for outstanding atmosphere. With outdoor dining, bonfires and lawn games all summer long, this is more a destination than a mere eatery.
Insider Tip: “Bites” are small so if you’re hungry we suggest ordering several items… or all of them for that matter! Their cocktails are to die for. Wash those delicious tacos down with one of their signature margaritas, sure to impress even the most radical marg-snob.
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Dream Away Lodge
1342 County Rd, Becket, Massachusetts 01223The legendary Dream Away Lodge is as dazzling as it it’s tricky to find. But as in any treasure hunt, the reward is worth its pursuit. If you are looking for a truly unique experience to dine, drink or just people watch, there is no better venue. Rumored to have been a brothel & speakeasy during the Great Depression, this brilliantly bohemian lodge in the woods has been patronized by the likes of Bob Dylan, Joan Baez, Arlo Guthrie & Allen Ginsberg. The food you ask? Amazing... The Dream Away boasts an eclectic, internationally inspired, and seasonal menu, chock-full of locally sourced ingredients. As you explore both the farmhouse-turned-“lodge” and its wildflower-strewn grounds, the charm seemingly never ends. It’s safe to say no two nights here are ever the same. From its nightly live entertainment and tchatche lined walls, to it’s mismatched dinnerware and engaging atmosphere, your experience at The Dream Away is likely to be a highlight of your time in the Berkshires.
Insider Tip: Be sure to check their events calendar regularly, as the Dream Away hosts a variety of entertainment- live music, theatre, spoken word, and much more. You may even stumble upon that unknown indie band you've been binge-listening to on the roster.
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Old Inn on the Green
134 Hartsville-New Marlboro Road, New Marlborough, Massachusetts 01230In today’s digital age it is not uncommon to feel disconnected from your roots, and the idea of traveling back to a simpler era has become increasingly romantic. Many folks flock from their respective cities to the Berkshires for the opportunity to slow down and decompress. If these are things you can relate to, then the experience you will have at the Old Inn on the Green is not only something you want, it’s something you need! The Old Inn provides it’s guests the “off-the-grid” opportunity to truly disconnect and reacquaint oneself to the unadulterated and uninterrupted beauty of a turn-of-the-century, fine dining experience. A departure from the flame-less candle trend of recent years, you’ll find kindled sconces, chandeliers and tapers adorning seemingly every surface of the dining rooms. In the wintertime, enjoy fireplaces glowing in each room, and in summer, the option to dine outside under white canopy. Boasting several menu formats to match any occasion (a la carte, prix fixe, Chef’s tasting menu, and on select days a “welcome menu” which changes daily) this culinary gem has drawn highbrow foodies from all over the map.
Insider Tip: Find yourself in New Marlborough in the morning or afternoon hours? Down the road is the Old Inn’s Southfield Store. Previously a general store dating back to 1907, The Southfield Store serves up mouthwatering baked goods, breakfast, brunch, lunch (and dinner seasonally). Open May through November 1st.
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Old Mill
53 Main Street, South Egremont, Massachusetts 01258The Old Mill has been a Berkshire dining favorite for over thirty-five years, serving seasonal, contemporary New England cuisine. Upon entering the dining room of this charming 1700’s grist mill, you will immediately notice a rustic elegance from wide plank floor to chestnut beam ceiling. A wood-burning forge creates a cozy atmosphere, perfect for date night with your special someone or dinner with friends. Located in the scenic heart of South Egremont, The Old Mill is easily one of South County’s best dining experiences when it comes to both food and ambiance. Looking for an entree suggestion? Though we hate to play favorites the Panko Crusted Rainbow Trout paired with a crisp glass of sauvignon blanc from their carefully selected wine list is sure to please your palate.
Insider Tip: Though we love The Old Mill any time of the year, it has a particularly magical feel around the holidays. What better way to get into the spirit this winter than an evening amongst the warm and festive ambiance that this local favorite radiates?
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PUBLIC Eat + Drink
34 Holden Street, North Adams, Massachusetts 01247Locally sourced ingredients, hip patrons, super friendly servers and craft brews... what more could you ask for? This little gem in North County offers a gastro-pub style menu done right. The restaurant is a local favorite, and being so is typically bustling on any given night. This is a great option to start your night out with a group of friends, cocktails and apps or a casual date night. Out of this world burgers, decadent pasta dishes, and flatbreads and unexpected items like falafel and PEI mussels bring this "pub" up a few (dozen) notches.
Insider tip: Public eat + drink is walking distance from the not-to-miss Mass MoCA. Work up your appetite while perusing contemporary art and end the day at PUBLIC!
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The Lion's Den at The Red Lion Inn
30 Main Street, Stockbridge, Massachusetts 01262Located in the basement of the historically famous Red Lion Inn of Stockbridge, the Lion’s Den is an underground lounge with an intimate speakeasy vibe that appeals to a fun music loving crowd. The inn itself has been welcoming guests from around the world for over two centuries, and is bursting with interesting ambiance, history and culture. Downstairs in “The Den”, patrons will enjoy tasty pub fare with a side of entertainment seven nights a week. All genres of music can be heard on any given evening, including folk, R&B, reggae and blues. Even some nationally recognized performers have been known to grace this pub stage from time to time, with Berkshires local James Taylor among them. Eat, drink and be merry...you never know who you might see!
Insider Tip: If you have come to hear the sweet sounds of local musicians play, it would be wise to arrive early on weekends to claim your seat. A fun place to see and be seen, the Lion’s den is always hopping with locals and tourists of all ages.
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The Wheatleigh
11 Hawthorne Rd, Lenox, Massachusetts 01240If a world-class dining experience is what you're after, look no further than The Wheatleigh. Nestled in the lush greenery of Lenox's (arguably) most beautiful road, this Guilded Age "summer cottage" turned hotel and dining room is an experience well worth its lofty price tag. Offering a seasonal four-course dining menu, you'll find imaginative flavor combinations and exotic ingredients. Even the most discerning foodie is sure to depart with stars in their eyes.
Insider Tip: If a formal four-course meal is out of the question, be sure to check out The Library. A more affordable alternative to their dining room, the Library offers a la carte lunch and dinner menus boasting the likes of fresh house-made pasta, soup, salads and, of course, escargot.
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