TOP 30 Charming restaurant in Stockbridge, Massachusetts

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!

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.

Stockbridge General Store is a charming and historic institution located in the heart of Stockbridge, Massachusetts. Situated at 40 Main Street, this beloved local spot offers a wide range of food, groceries, and household essentials. From fresh produce and baked goods to pantry staples and unique artisanal products, Stockbridge General Store has everything you need for your everyday shopping needs. Whether you're a resident stocking up on necessities or a visitor looking for a taste of local flavor, this quaint store is a must-visit destination in Stockbridge. With its friendly staff, cozy atmosphere, and convenient location, Stockbridge General Store is a true gem in the community.

Michaels of Stockbridge is a vibrant establishment located at 5 Elm Street in the charming town of Stockbridge, Massachusetts. This institution offers a unique combination of a bar, restaurant, night club, and food experience all under one roof. Guests can enjoy delicious meals prepared with fresh, local ingredients, sip on expertly crafted cocktails, and dance the night away in a lively atmosphere. Whether you're looking for a casual meal with friends, a night of entertainment, or a fun night out, Michaels of Stockbridge has something for everyone. Come and experience the lively ambiance and exceptional hospitality at this popular destination in Stockbridge.

West Stockbridge is a charming institution located at 47 Albany Road in the picturesque town of West Stockbridge, Massachusetts. This historic institution offers a unique blend of cultural experiences, including art galleries, live music performances, and community events. Visitors can explore the quaint shops and restaurants in the area, or simply enjoy the scenic beauty of the Berkshire Mountains. West Stockbridge is a must-visit destination for anyone looking to immerse themselves in the rich history and vibrant culture of this New England town.

Welcome to Alice's Restaurant, the original location nestled in the charming town of Stockbridge, Massachusetts. Situated in the heart of the Berkshires, our restaurant offers a warm and inviting atmosphere where culinary tradition meets modern flair. Known for our farm-to-table approach, we pride ourselves on serving delicious, locally-sourced dishes that celebrate the rich flavors of New England. At Alice's Restaurant, we offer a diverse menu that caters to all tastes, featuring classic American favorites with a contemporary twist. From hearty breakfasts to delectable dinners, each meal is crafted with care by our talented chefs. Our cozy dining room and friendly staff ensure a memorable dining experience for locals and visitors alike.

Welcome to 249 Stockbridge Road Parking, your convenient and reliable parking solution in the heart of Great Barrington, Massachusetts. Located at 249 Stockbridge Road, our facility offers easy access to local attractions, shopping, and dining, making it the perfect spot to park your vehicle while you explore all that this charming town has to offer. Our well-maintained parking area provides ample space for cars, ensuring a hassle-free experience for both short-term visitors and long-term guests. Whether you're here for a quick visit or an extended stay, our competitive rates and flexible parking options are designed to meet your needs.

Travelodge by Wyndham Great Barrington Berkshires is a cozy and comfortable lodging option located at 400 Stockbridge Road in the charming town of Great Barrington, Massachusetts. Situated in the picturesque Berkshires region, this hotel offers convenient access to local attractions, restaurants, and outdoor activities. The rooms are clean and well-appointed, providing guests with a relaxing retreat after a day of exploring. The friendly staff is always ready to assist with any needs or questions, ensuring a pleasant stay for all visitors. Whether you are in town for business or leisure, Travelodge by Wyndham Great Barrington Berkshires is the perfect choice for your accommodations.

Thornewood Inn is a charming and historic lodging located at 453 Stockbridge Road in the picturesque town of Great Barrington, Massachusetts. Nestled in the heart of the Berkshires, this cozy inn offers a tranquil escape for guests looking to relax and unwind. The beautifully appointed rooms are elegantly furnished and offer modern amenities for a comfortable stay. Guests can enjoy a delicious breakfast each morning and explore the surrounding area, which is known for its scenic beauty and cultural attractions. Whether you are seeking a romantic getaway or a peaceful retreat, Thornewood Inn is the perfect destination for your next vacation.

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.

Rio Cafe is a charming cafe and restaurant located at 403 Stockbridge Road in Great Barrington, Massachusetts. This cozy establishment offers a variety of delicious food options, including freshly brewed coffee, hearty breakfast dishes, scrumptious sandwiches, and delectable desserts. With a warm and inviting atmosphere, Rio Cafe is the perfect spot to relax and enjoy a meal with friends or family. Whether you're looking for a quick bite to eat or a leisurely dining experience, Rio Cafe has something for everyone to enjoy. Come visit us and experience the delicious flavors and friendly service that make Rio Cafe a beloved local favorite.

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.

The Kemble Berkshires is a historic lodging institution located at 2 Kemble Street in Lenox, Massachusetts, United States. Originally built in the 1880s for a U.S. Secretary of State and New Jersey State Senator, the property has been newly renovated by Shared Estates with modern finishes and luxurious amenities. The estate features manicured landscaping with stunning views of the Stockbridge Bowl. Guests can enjoy various spaces within the property, including a library room, music room, private bar, and seven fireplaces. The Kemble is 100% carbon neutral and can accommodate events for up to 175 guests. The property offers a dining room, professional kitchen, herb and vegetable garden, fire pit, and multi-level stone patios and decks. Guests can enjoy a wide range of amenities, including a virtual reality gaming room, retro arcade, outdoor sports equipment, and more. The Kemble Berkshires is owned by 143 investors through Shared Estates' equity crowdfunding model, making it a unique social equity vehicle in the real estate industry.

Conroy's Bed & Breakfast is a charming lodging establishment located at 11 East Street in the picturesque town of Stockbridge, Massachusetts, United States. Nestled in a quaint and peaceful neighborhood, this cozy bed and breakfast offers comfortable accommodations and warm hospitality for guests looking to relax and unwind in a homely atmosphere. With its convenient location near local attractions, shops, and restaurants, Conroy's Bed & Breakfast is the perfect choice for travelers seeking a memorable stay in the heart of Stockbridge.

Once Upon a Table is a charming restaurant located at 36 Main Street in Stockbridge, Massachusetts. This cozy establishment offers a delightful dining experience with a menu filled with delicious dishes made from locally sourced ingredients. The warm and inviting atmosphere of Once Upon a Table makes it the perfect spot for a romantic dinner or a casual meal with friends. Whether you're craving a hearty burger or a gourmet salad, this restaurant has something for everyone. Come and enjoy a memorable dining experience at Once Upon a Table.

Main Street Cafe is a charming eatery located at 40 Main Street in the picturesque town of Stockbridge, Massachusetts. This cozy restaurant offers a warm and inviting atmosphere where guests can enjoy delicious food and drinks. The menu features a variety of classic American dishes made with fresh, locally sourced ingredients. Whether you're looking for a hearty breakfast, a leisurely lunch, or a satisfying dinner, Main Street Cafe has something for everyone. Stop by and experience the friendly service and mouthwatering meals that have made this cafe a beloved dining destination in Stockbridge.

Tanglewood Cafeteria is a charming eatery located in Stockbridge, Massachusetts, United States. This cozy restaurant offers a wide variety of delicious food options for patrons to enjoy. From hearty breakfasts to satisfying lunches and dinners, Tanglewood Cafeteria has something for everyone. Guests can relax in the welcoming atmosphere and savor their meals while taking in the beautiful surroundings of Stockbridge. Whether you're in the mood for a comforting bowl of soup, a fresh salad, or a tasty sandwich, Tanglewood Cafeteria is the perfect spot to satisfy your cravings. Come visit us and experience the delectable flavors and warm hospitality that make Tanglewood Cafeteria a must-visit destination in Stockbridge.

Taste of the Berkshires is a charming restaurant located in Stockbridge, Massachusetts, offering a delightful culinary experience that showcases the best flavors of the region. Our menu features a variety of locally sourced ingredients and dishes that highlight the rich culinary tradition of the Berkshires. From farm-to-table entrees to decadent desserts, every dish is carefully crafted to tantalize your taste buds and leave you craving for more. Come and experience the true essence of the Berkshires at Taste of the Berkshires.

Tiffany's Cafe & Market is a charming establishment located in the heart of Stockbridge, Massachusetts. This unique cafe offers a cozy atmosphere where guests can enjoy freshly brewed coffee, delicious pastries, and a variety of homemade sandwiches and salads. In addition to their cafe offerings, Tiffany's also features a market where visitors can purchase locally sourced produce, artisanal cheeses, and gourmet pantry items. Whether you're looking for a quick bite to eat or a special ingredient for your next meal, Tiffany's Cafe & Market has something for everyone. Visit them at 4 Elm Street for a delightful culinary experience in Stockbridge.

Barrington Plaza is a bustling shopping mall located at 334 Stockbridge Road in the charming town of Great Barrington, Massachusetts. This popular destination offers a wide variety of shops, restaurants, and entertainment options for visitors of all ages. Whether you're looking for the latest fashion trends, unique gifts, or a delicious meal, Barrington Plaza has something for everyone. Come explore all that this vibrant shopping center has to offer in the heart of beautiful Great Barrington.

Sidetracks is a charming store located at 8 Elm Street in Stockbridge, Massachusetts. This unique institution offers a diverse selection of items, ranging from home decor and gifts to clothing and accessories. With its cozy atmosphere and friendly staff, Sidetracks is the perfect place to find that special something for yourself or a loved one. Whether you're looking for a one-of-a-kind piece of jewelry or a stylish home accent, you're sure to discover something wonderful at Sidetracks. Visit us today and see why we're a favorite destination for shoppers in Stockbridge.

No. Six Depot Roastery & Cafe is a charming and cozy establishment located at 6 Depot Street in the picturesque town of West Stockbridge, Massachusetts. This unique cafe doubles as a roastery, offering a wide selection of freshly roasted coffees and teas for purchase. The warm and inviting atmosphere makes it the perfect spot to relax and enjoy a delicious meal or snack, with a menu featuring a variety of locally sourced and organic ingredients. In addition to their food and beverage offerings, No. Six Depot also has a small store where visitors can purchase coffee beans, tea leaves, and other artisanal products to take home. Whether you're looking for a quick pick-me-up or a leisurely meal, No. Six Depot Roastery & Cafe is the ideal destination for food and coffee enthusiasts alike.

Main Street Catering is a premier food institution located at 30 Main Street in the charming town of Stockbridge, Massachusetts, United States. Known for its exceptional culinary creations and top-notch service, Main Street Catering is the go-to choice for all your catering needs. Whether you're planning a wedding, corporate event, or private party, Main Street Catering will impress your guests with delicious and beautifully presented dishes. With a focus on using fresh, locally sourced ingredients, Main Street Catering is committed to providing a memorable dining experience for all. Visit us today and let us take care of all your catering needs.

Cindy's Cafe is a cozy and inviting eatery located in the charming town of Stockbridge, Massachusetts, United States. Serving up delicious meals made with fresh, locally sourced ingredients, this cafe is a favorite among locals and visitors alike. Whether you're stopping in for a hearty breakfast, a light lunch, or a sweet treat, Cindy's Cafe has something for everyone. With friendly service and a welcoming atmosphere, it's the perfect spot to relax and enjoy a tasty meal in the heart of Stockbridge.

Truc Orient Express is a delightful culinary gem located at 3 Harris St, West Stockbridge, MA 01266, United States. Specializing in authentic and exquisite Asian cuisine, this charming restaurant offers a diverse menu that captures the rich and vibrant flavors of the Orient. Whether you're in the mood for a comforting bowl of pho, a flavorful stir-fry, or expertly crafted sushi, Truc Orient Express promises a memorable dining experience that celebrates the artistry and tradition of Asian cooking. The warm and inviting atmosphere, coupled with attentive service, makes it an ideal spot for both casual meals and special occasions.

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 Mill Brook Sugarhouse, a cherished staple in the heart of Lenox, Massachusetts, where we have been crafting Pure Maple Syrup for over 40 years. Located at 409 New Lenox Road, our sugarhouse is more than just a place to enjoy delicious food; it's a celebration of tradition and quality. Join us this summer at the Lenox and West Stockbridge farmers markets, where you can discover our wide range of maple syrup options. Whether you're a local resident or visiting the beautiful Berkshires, you'll never have to worry about running out of our sweet, golden syrup.

Welcome to the William "Officer Obie" Obanhein Grave Site, a unique historical landmark nestled in the charming town of Stockbridge, Massachusetts. Located at 1 Main Street, this site pays tribute to the iconic local figure, Officer Obie, who gained fame through his portrayal in the classic folk song "Alice's Restaurant" by Arlo Guthrie. Visitors to the grave site can explore the rich history and legacy of Officer Obie, who served as the Stockbridge police chief and became a symbol of the town's vibrant culture in the 1960s. The site offers a serene and reflective setting for those interested in learning more about this fascinating piece of Stockbridge's past.

Welcome to Tappan Manor House, a charming and historic retreat nestled in the heart of Stockbridge, Massachusetts. With its timeless elegance and serene surroundings, Tappan Manor House offers an unforgettable experience for all visitors. Our beautifully restored manor is a testament to classic architecture, featuring exquisite interiors and meticulously maintained grounds. Located in the picturesque Berkshires, Tappan Manor House provides a perfect escape for those seeking tranquility and relaxation. Whether you're here for a romantic getaway, a family vacation, or a special event, our dedicated staff is committed to ensuring your stay is both comfortable and memorable. Enjoy our luxurious accommodations, savor delicious local cuisine, and explore the natural beauty and cultural attractions that Stockbridge has to offer.