Food & Drinks

Food and drink are at the heart of any Berkshire getaway, and Little Lion Inn puts you close to it all. Located just minutes from Great Barrington and a short drive from Stockbridge and Lenox, guests have easy access to the region’s best restaurants, cafés, breweries, and cocktail bars. From farm-to-table dining and cozy brunch spots to wine tastings and craft beer, there’s something for every taste. Looking to stay in? Pick up local provisions, enjoy a casual picnic, or unwind with takeout in the comfort of your room.

Food & Drinks

Person serving themselves food at a meal, with a plate of pasta, bread, and other dishes on a table.

  • Just a short drive from Little Lion Inn, The Red Lion Inn in Stockbridge offers a classic New England dining experience in a historic setting. From the elegant Main Dining Room to the more casual Widow Bingham’s Tavern, guests can enjoy seasonal menus, locally inspired dishes, and an award-winning wine list. Whether you’re planning a special evening out or a relaxed meal, it’s a quintessential Berkshire dining experience not to be missed.

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Golden retriever dog smiling in front of an outdoor sign for the 'Baked Box' restaurant, with a picnic table and red umbrella, green grass, and a blue sky with clouds.

  • The Bistro Box in Great Barrington is a local favorite for casual, outdoor dining with a creative twist. Known for its inventive burgers, fresh salads, and house-made sides, this laid-back spot is perfect for a quick, satisfying bite. With picnic-style seating and a fun, welcoming atmosphere, it’s an easy go-to for lunch or a relaxed dinner during your Berkshire stay.

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A table set with a floral centerpiece, a glass candle holder, a plate of roasted chicken with vegetables, and a charcuterie board with sliced bread, cheese, strawberries, radishes, and greens.

  • This quaint, intimate bistro tucked away in an alley features locally sourced American dishes.

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Sunset sky with orange and pink clouds above a dark building with a sign that reads 'cafeADAM' and some trees in the foreground.

  • This local sanctuary serves up seasonal menus and an impressive wine list in the historical Jenifer House Commons in Great Barrington.

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Exterior view of ALTA restaurant and wine bar with hanging flower baskets and a flower box on the windowsill, showing an open window with tables inside and staff preparing inside.

  • This bistro-style restaurant offers inspired Mediterranean cuisine, an extensive wine list (with 24 wines by the glass) and outdoor dining.

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Inside view of a cozy coffee shop with a wooden counter, glass display case, and chalkboard menu. Chairs and tables are arranged for customers, with condiment bottles and cleaning spray on the table.

  • Neighborhood dinner-style menu serving your favorite classics

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A cozy, dimly lit bar with a long wooden counter and high chairs, bottles of liquor on shelves, and a fireplace with a floral arrangement on the counter nearby.

  • Wine & beer bar offering bites such as pizza, cheese & charcuterie in intimate surrounds.

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Exterior of a Mediterranean restaurant named Aegean Breeze with signs advertising burgers, gyros, falafel, and take-out, decorated with pumpkins and autumn plants, American flag flying outside.

  • Rustic tavern serving Greek provisions, known for its grilled whole fish

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People enjoying a meal with multiple plates of pizza, salad, and drinks on a table at a restaurant.

  • Pizzeria Boema in Lenox serves up wood-fired, Neapolitan-style pizzas in a warm, inviting setting. Known for its perfectly blistered crusts, fresh ingredients, and simple, authentic flavors, it’s a go-to spot for a relaxed meal. Pair your pizza with a glass of wine or a craft cocktail for an easy, satisfying dining experience in the Berkshires.

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A large dark blue house with white trim, multiple windows, and a porch, surrounded by green trees and plants under a blue sky. A sign reads 'Prairie Whale Outdoor Dining'.

  • Prairie Whale in Great Barrington is a beloved Berkshire dining spot known for its rustic charm and ingredient-driven menu. Focused on locally sourced meats and seasonal produce, the restaurant offers a warm, lively atmosphere and thoughtfully crafted dishes that celebrate the region’s farms. It’s an ideal choice for a relaxed yet elevated night out.

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Interior of a restaurant filled with people dining at tables with white tablecloths, large windows letting in natural light, decorative ceiling panels, and bottles of wine on shelves along the wall.

  • A modern French bistro boasting fine cuisine and a sleek bar area that contains a zinc bar and a world class gallery of photographs and art. Downtown Lenox.

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White building with outdoor patio, sign for Frankie's Italian restaurant, sidewalk, and adjacent red brick building

  • Frankie’s Ristorante in Lenox offers classic Italian comfort in a warm, welcoming setting. Known for its house-made pastas, hearty entrées, and traditional recipes, it’s a go-to for a relaxed, satisfying meal. Whether you’re craving a cozy dinner or a casual night out, Frankie’s delivers timeless flavors and generous hospitality.

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Front porch of a white house with a red door, stairs, and outdoor seating, surrounded by trees and plants, with flags and a sign indicating reopening on May 29, 1969.

Our Sister Property,
The Red Lion Inn

Little Lion Inn is a sister property to the historic Red Lion Inn in Stockbridge, a landmark destination known for its rich history and warm hospitality. Guests of Little Lion can easily enjoy the best of both experiences: modern simplicity paired with access to one of the Berkshires’ most iconic inns. From dining in the Main Dining Room or Widow Bingham’s Tavern to enjoying live music in the Lion’s Den, seasonal outdoor experiences, and classic New England charm, the Red Lion Inn offers an extension of your stay just a short drive away. It’s the perfect balance of laid-back, design-forward lodging and timeless Berkshire tradition.

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Two people sitting in red chairs on a grassy lawn, facing away from the camera, with a small dog lying on the grass nearby. Behind them is a large green building with windows and a roof with small cupola structures. In the background, there is a forested hillside with trees and mountains under a bright sky. Power lines are visible in the sky.
A happy curly-haired dog with a red collar sitting on a neatly made bed in a modern bedroom with white bedding, framed photos on the wall, and matching side lamps.
A couple walking hand-in-hand in a park with a small brown dog. The park has lush green trees and grass, with a wooded hill in the background. The woman has long brown hair and is wearing a white top, while the man has short dark hair and is wearing a dark shirt and shorts.
A pink patio umbrella over a wooden picnic table outdoors in a park with green trees and a clear blue sky.
A cozy bedroom with two beds, a stone accent wall, wall art, a nightstand with a lamp, and a sitting area by a window with curtains.

Our Rooms & Amenities

Our guestrooms at Little Lion Inn offer a comfortable, design-forward stay in the Berkshires, blending retro-modern style with thoughtful amenities. Each room features plush bedding, modern conveniences, and inviting details designed for a relaxing and effortless experience. Guests enjoy easy, contactless check-in, pet-friendly accommodations, and access to nearby dining, shopping, and outdoor activities. Whether you're planning a weekend getaway in Great Barrington or an extended Berkshires stay, Little Lion Inn provides the perfect mix of comfort, convenience, and boutique charm.

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