TOP 10 Wine and dine experiences in Stockbridge, Massachusetts

Cafe Adam, Bar and Restaurant is a charming establishment located at 420 Stockbridge Road in Great Barrington, Massachusetts. This versatile venue offers a cozy and inviting atmosphere perfect for enjoying a delicious meal, grabbing a drink at the bar, or even staying overnight in their comfortable lodging accommodations. The restaurant serves up a diverse menu featuring a range of culinary delights, from classic American dishes to international cuisine. Whether you're looking for a casual meal with friends or a romantic dinner for two, Cafe Adam has something for everyone. Come and experience exceptional hospitality and delectable fare at this hidden gem in the heart of the Berkshires.

Queensboro Wine & Spirits is a charming food and liquor store located in the heart of West Stockbridge, Massachusetts. Situated at 26 Main Street, this establishment offers a wide selection of fine wines, spirits, and gourmet foods. Whether you are looking for a special bottle of wine for a dinner party or a unique gift for a loved one, Queensboro Wine & Spirits has something for every occasion. With knowledgeable staff and a welcoming atmosphere, this store is a must-visit destination for anyone in the area looking to elevate their dining and entertaining experiences.

Aegean Breeze Restaurant is a charming Mediterranean eatery located at 327 Stockbridge Road in the picturesque town of Great Barrington, Massachusetts. Our cozy restaurant is known for its warm and inviting atmosphere, as well as its delicious and authentic Mediterranean cuisine. From freshly grilled kebabs to flavorful hummus and crispy falafel, our menu is sure to satisfy any craving for Mediterranean flavors. Come and experience the taste of the Aegean at Aegean Breeze Restaurant today!

Marketplace Kitchen Table is a cozy cafe and restaurant located at 240 Stockbridge Road in Great Barrington, Massachusetts. They offer a variety of delicious dishes that are prepared and ready to be reheated and served. On Carvery Night, they serve up a mouthwatering Roast Rib of Beef with all the fixings. You can order individual dinners or dinners for four at their Specialty Shop. In addition to their food offerings, Marketplace Kitchen Table also has a selection of specialty wines available for purchase. They offer a range of sparkling, rose, white, and red wines that pair perfectly with their menu items.

AMICI is a charming Italian restaurant located at 5 Albany Road in West Stockbridge, Massachusetts. Known for its warm and inviting atmosphere, AMICI offers a wide range of delicious Italian dishes made with fresh, locally sourced ingredients. From homemade pastas to wood-fired pizzas, there is something for everyone to enjoy at this cozy eatery. Whether you're looking for a casual dinner with friends or a romantic date night, AMICI is the perfect spot to indulge in authentic Italian cuisine. Come visit us and experience the true taste of Italy in the heart of West Stockbridge.

Located at 30 Main Street in Stockbridge, Massachusetts, The Red Lion Inn is a historic landmark of hospitality that has been welcoming guests for 250 years. The property includes the original Main Inn, a contemporary guest house, and unique lodging options like the turn-of-the-century Firehouse. Enjoy the heated outdoor pool, Hot Tub, and Pool House stocked with fresh towels and games. The culinary experience at The Red Lion Inn is top-notch, with seasonal menu items sourced from local farmers, craft cocktails, and an award-winning wine selection. Live music at The Lion’s Den adds to the vibrant atmosphere. Guests rave about the cozy rooms, delicious food, and exceptional service. Don't miss out on the curated packages and experiences to make the most of your stay in the Berkshires. The Red Lion Inn is a proud member of Historic Hotels of America and the National Trust for Historic Preservation. Come experience the charm and history of The Red Lion Inn for yourself.

Welcome to Heirloom Lodge, your premier dining destination nestled in the charming town of West Stockbridge, Massachusetts. Located at 286 Great Barrington Road, our restaurant offers a unique culinary experience that celebrates the rich flavors and traditions of New England cuisine. At Heirloom Lodge, we pride ourselves on creating a warm and inviting atmosphere where guests can enjoy exceptional food crafted from the finest locally-sourced ingredients. Our menu features a delightful array of dishes that showcase the best seasonal produce, meats, and seafood from the region, expertly prepared by our talented chefs.

Welcome to Truck’s Orient Express Restaurant, a unique bar located in the heart of West Stockbridge, Massachusetts. Situated at 3 Harris Street, our establishment offers a cozy and inviting atmosphere where locals and visitors alike can unwind and enjoy a memorable experience. At Truck’s Orient Express, we pride ourselves on our diverse selection of beverages, featuring craft beers, fine wines, and expertly mixed cocktails that cater to every palate. Our talented bartenders are passionate about creating the perfect drink to complement any occasion, whether you're here to celebrate with friends or simply relax after a long day.

Welcome to Lakeside Bar & Grill, your premier destination for delicious dining in Lanesborough, Massachusetts. Nestled at 750 South Main Street, right on the stunning shores of Pontoosuc Lake, our restaurant offers a delightful escape with breathtaking views and a warm, friendly atmosphere. At Lakeside Bar & Grill, we pride ourselves on serving a variety of fresh seafood and pasta dishes that are sure to satisfy every palate. From full-belly clams and hot or cold lobster rolls to perfectly fried calamari and shrimp, our menu is a celebration of the sea, complemented by our signature cheeseburgers, sandwiches, and wraps. Whether you're a seafood aficionado or a burger enthusiast, our diverse offerings promise something for everyone.

Welcome to The Shaker Mill, your quintessential gathering spot nestled in the heart of West Stockbridge, Massachusetts. Located at 1 Depot Street, our charming establishment offers a unique blend of rustic elegance and modern comfort, perfect for both locals and visitors looking to unwind and enjoy a memorable experience. At The Shaker Mill, we pride ourselves on our warm and inviting atmosphere, where our friendly staff is dedicated to making you feel at home. Whether you're stopping by for a casual drink with friends, a cozy dinner, or a special celebration, you'll find our diverse menu and extensive selection of craft cocktails, fine wines, and local brews sure to delight your palate.

Welcome to Ella May's, your go-to destination for delightful culinary experiences and gourmet essentials, nestled in the heart of West Stockbridge, Massachusetts. Located at 30 Main Street, our charming store invites you to explore an exquisite selection of locally sourced and internationally inspired foods. Whether you're seeking artisanal cheeses, freshly baked goods, or unique pantry staples, Ella May's promises a curated shopping experience that caters to food enthusiasts and casual shoppers alike. Our friendly staff is dedicated to providing personalized service and expert recommendations to enhance your culinary adventures. Visit Ella May's today and discover a world of flavors that will tantalize your taste buds and elevate your dining experiences.

Welcome to Mezze Guesthouse, a serene retreat nestled above the renowned Mezze Bistro in the picturesque town of Williamstown, Massachusetts. Located at 777 Cold Spring Road, our guesthouse offers a harmonious blend of contemporary comfort and classic Mezze hospitality. Our guesthouse features five uniquely designed units, each adorned with custom finishes such as Grohe rain showers, K-Fee coffee-makers, and locally sourced treats. Choose from three elegant queen-sized units, a spacious two-bedroom suite with a queen bedroom and twin room, or indulge in our luxurious King suite complete with a separate sitting room and an oversized bathroom.