The Berkshires Restaurants

We’ve compiled the best of the best in The Berkshires - browse our top choices for Restaurants during your stay.

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  • 1. Alpamayo

    $$

    Don't let the no-frills decor fool you; what this family-owned restaurant lacks in style it more than makes up for in bold flavors, especially at dinner. Enjoy a menu of fresh and flavorful Peruvian favorites ranging from ceviche to plantains, and don't forget to grab a caramel custard for dessert.

    60 Main St., Massachusetts, 01238, USA
    413-243–6000

    Known For

    • Chicha morada (incredible purple corn drink)
    • Lomo saltado (steak strips sauteed with tomatoes, onions, and fries)
    • Peruvian corn on the cob

    Restaurant Details

    Rate Includes: Closed Mon.
  • 2. Chocolate Springs Cafe

    $

    Escape into chocolate bliss here, where even the aromas are intoxicating. This award-winning chocolatier offers wedges of decadent cakes, ice creams, and sorbets, and dazzling chocolates all made on-site. Whether you like your chocolate dark and pure, sugar-free—even with a chipotle filling—you can't go wrong. You can eat at one of a handful of leather couches or wooden chairs and tables, but don't expect so much as a salad or a wrap: it's all chocolate, all the time.

    55 Pittsfield/Lenox Rd., Massachusetts, 01240, USA
    413-637–9820

    Known For

    • Decadent hot chocolate
    • Truffles, truffles, truffles
    • Perfect, prepackaged gift boxes for any occasion
  • 3. Coyote Flaco

    $

    The best Mexican food in the Berkshires can be found at this unassuming spot where traditional cuisine meets local ingredients. The menu is small but every item is done well, and often served with side dishes in cute little tortilla cups.

    505 Cold Spring Rd., Massachusetts, 01267, USA
    413-458–4240

    Known For

    • Enchilada Oaxaca with mole sauce
    • Delicious margaritas
    • Nightly specials

    Restaurant Details

    Rate Includes: Closed Mon. and Tues. No lunch
  • 4. District Kitchen & Bar

    $$

    Delicious food and good wine keep this small restaurant packed most nights. This gem can almost be missed just off busy North Street, but couples looking for an intimate date-night or professionals grabbing after-work drinks have made it a hot spot.

    40 West St., Massachusetts, 01201, USA
    413-442–0303

    Known For

    • Delicious burgers
    • House fries with aioli sauce you won't want to share
    • Small rotating seasonal menu
  • 5. The Bistro Box

    $

    Just a short drive from the busy downtown you'll find this seasonal road-side food shack that always has a line of locals waiting to order the famous Box Burger with hand-cut parmesan and truffle oil fries. Fresh lobster and crab rolls, fish tacos, and pulled pork sandwiches with rhubarb barbecue sauce are the last thing you'd expect to find at this eclectic spot along a busy road out of town.

    937 Main St., Massachusetts, 01230, USA
    413-717–5958

    Known For

    • Delicious burgers and hand-cut fries
    • Freshly squeezed lemonade and fruit slushies
    • Spring Fries made with ramp pesto, wild mushrooms, goat cheese, and a balsamic reduction

    Restaurant Details

    Rate Includes: Closed Wed. and Nov.–Apr.
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