Discover the Berkshires

  • Things to Do
  • Places to Stay
  • Food & Drink
  • Blog

Cheshire, MA

Cheshire, MA is a charming town in the heart of the Berkshires, known for its scenic beauty, historic sites, and friendly community. Located midway between Pittsfield and North Adams, Cheshire is a convenient base camp for exploring all that the Berkshires have to offer.

Bass Water Grill

Bass Water Grill offers casual lakeside dining. Full menu including pasta, seafood, steaks and full bar.
View More

Harbour House Inn

Harbour House Inn B&B exudes 18th-century New England charm. Revel in Georgian Colonial luxury with gourmet delights in Harbor House Inn.
View More

Harbour House Inn B&B

Harbour House Inn B&B is a beautiful and historic 18th Century Georgian Colonial. Centrally located near many area attractions.
View More

The Cobbles

Enjoy nature at its best with Cheshire Cobbles via the Appalachian Trail near Cheshire, MA. A dog-friendly moderate trail with beautiful flora.
View More

Whitney’s Farm Market

Whitney's Farm Market is a full service garden center offering: fresh produce, grinders, wraps, & sandwiches, full deli & bakery, homemade pies & breads, famous cider donuts & maple donuts and propane refills.
View More

Whitney’s Farm Market & Garden Center

Whitney's Farm Market & Garden Center offers a large variety of plants, garden curios, homegrown sweet corn, produce, deli, bakery. Pumpkin fest w/corn maze. Xmas trees. Petting zoo.
View More
You are here: Home / Archives for Towns / Cheshire
  • Discover more

    • Blog
    • Food & Drink
      • American
      • Asian
      • Bakeries/Coffee Shops
      • Breakfast
      • Brewery/Pubs
      • Ice Cream
      • Indian
      • Italian
      • Mediterranean (Greek)
      • Mexican
      • Pizza
    • Places to Stay
      • Bed & Breakfasts
      • Camping
      • Inns
      • Motels
      • Resorts
      • Vacation Rentals
    • Things to do
      • Arts & Culture
      • Recreation/Sports
      • Shopping
        • Antiques & Collectibles
        • Art Galleries
        • Book Stores
        • Clothing
        • Electronics
        • Food & Candy
        • Garden Center & Florists
        • Home Decor & Furniture
        • Jewelry & Accessories
        • Outdoors
        • Outlets & Shopping Centers
        • Specialty Shops
        • Toys
      • Spa & Fitness
      • Special Events
      • Swimming
      • Winter Sports
    • Towns
      • Adams
      • Becket
      • Cheshire
      • Clarksburg
      • Dalton
      • Egremont
      • Florida
      • Great Barrington
      • Hancock
      • Hinsdale
      • Lanesborough
      • Lee
      • Lenox
      • Monterey
      • Mount Washington
      • New Ashford
      • New Marlborough
      • North Adams
      • Otis
      • Pittsfield
      • Richmond
      • Sandisfield
      • Savoy
      • Sheffield
      • Stockbridge
      • Tyringham
      • Washington
      • West Stockbridge
      • Williamstown
      • Windsor

© 2026 ยท Discover The Berkshires
Contact us