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  • Hike Mount Greylock

    Mount Greylock is the highest peak in Massachusetts and offers stunning views of the countryside from the top. You can also drive to the summit and visit the Veterans War Memorial Tower. Visiting Mt. Greylock is an opportunity that you shouldn't pass up!

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  • Ashuwillticook Rail Trail

    The Ashuwillticook Rail Trail was originally an old railroad track, but now it's a paved trail great for walking, jogging, and especially biking. It's 12. 7 miles long and runs through several towns. You'll have spectacular views of Cheshire Reservoir and its local scenery and wildlife.

    Website
  • Ramblewild Aerial Adventure Park

    With over 10 acres of high wires, zip lines, rope ladders, balancing logs, cargo nets, and suspended bridges, there's plenty to explore at Ramblewild. There are plenty of family friendly sections that thrill children and adults alike!

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  • Jiminy Peak Adventure Course

    You'll find mountain coasters, super slides, rock climbing, swings, trampolines, and more at this fun, child-friendly adventure park. Make sure you buy your tickets early to make sure you get a spot!

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  • Hancock Shaker Village

    Visit the oldest working farm in the Berkshires. Hancock Shaker Village has 20 historic buildings set on 750 acres. Come experience history come to life and learn about an interesting time and people. There's always fun activities going on, too!

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  • Mass. Museum of Contemporary Art

    Enjoy art like you've never seen it before. MASS MoCA embraces all forms of art. Their boundary-crossing approaches to art bring some of the world's most brilliant minds to the museum year round.

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  • Norman Rockwell Museum

    Learn more about the iconic American artist, Norman Rockwell. Founded in 1969, this museum is one of the most popular cultural destinations in the Berkshires!

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  • ​​Hilltop Orchards & Furnace Brook Winery

    Enjoy hiking, wine tastings, and famous apple cider donuts at this 200 acre property. During the fall, you can also pick your own apples! There's a lot to do, see, and explore at Hilltop Orchards and Furnace Brook Winery.

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  • Berkshire Museum

    This museum has an eclectic collection of art and artifact from across the world. You'll learn about fossils, meteorites, mummies, and more!

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  • Donnybrook Golf Course

    Enjoy golfing in the Berkshires at Donnybrook Country Club. Their well-manicured grounds are a pleasure to golf on. Definitely stop by if you love golf, or if you're interested in learning!

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  • Jacob's Pillow

    Home to America's longest running international dance festival, Jacob's Pillow is a great place to enjoy the beauty of dancing from around the world. The grounds are also a great place to picnic. While you're here, be sure to check out the visitor's center, and take a photo at the famous Pillow Rock!

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  • Kayaking and Canoeing

    Berkshire Outfitters offer canoe and kayak rentals so you can explore the area's lakes and rivers. From hiking to fishing, they also offer a wide range of other rentals to meet your needs.

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  • Tanglewood

    Enjoy stunning musical performances at Tanglewood. Each summer they have tons of great performances lined up. Plan ahead and get tickets to a musical performance while here in the Berkshires.

    Website
  • U-Drive Boat Rentals

    Thanks to U-Drive Boat Rentals, you can enjoy a family trip on a luxurious pontoon boat without the trouble of transportation, maintenance, or gas.

    Website
  • Lanesboro Restaurant & Pizzeria

    Serving up Italian fare, including pizza, Lanesboro Restaurant and Pizzeria has been a staple for over 35 years.

    Website
  • Olde Forge Restaurant

    Serving the largest selection of imported and domestic beers in the country, Olde Forge Restaurant is a great spot for beer aficionados, or anyone looking for a great burger or other local food.

    Website
  • Tavern at The A

    Offering classic American fare alongside late-night food and dancing, this might be just the place you're looking for!

    Website
  • Water Street Grill

    Water Street Grill is casual and cozy, offering American food and more than 20 craft brews on tap. Whether you're looking for seafood, burgers, steak, or salad, they have you covered.

    Website
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Blank Page - test retail
Ashuwillticook Rail Trail

The Ashuwillticook Rail Trail was originally an old railroad track, but now it's a paved trail great for walking, jogging, and especially biking. It's 12. 7 miles long and runs through several towns. You'll have spectacular views of Cheshire Reservoir and its local scenery and wildlife.
Website
Ramblewild Aerial Adventure Park

With over 10 acres of high wires, zip lines, rope ladders, balancing logs, cargo nets, and suspended bridges, there's plenty to explore at Ramblewild. There are plenty of family friendly sections that thrill children and adults alike!
Website
Mass. Museum of Contemporary Art

Enjoy art like you've never seen it before. MASS MoCA embraces all forms of art. Their boundary-crossing approaches to art bring some of the world's most brilliant minds to the museum year round.
Website
Norman Rockwell Museum

Learn more about the iconic American artist, Norman Rockwell. Founded in 1969, this museum is one of the most popular cultural destinations in the Berkshires!
Website
Donnybrook Golf Course

Enjoy golfing in the Berkshires at Donnybrook Country Club. Their well-manicured grounds are a pleasure to golf on. Definitely stop by if you love golf, or if you're interested in learning!
Website
Jacob's Pillow

Home to America's longest running international dance festival, Jacob's Pillow is a great place to enjoy the beauty of dancing from around the world. The grounds are also a great place to picnic. While you're here, be sure to check out the visitor's center, and take a photo at the famous Pillow Rock!
Website
Tanglewood

Enjoy stunning musical performances at Tanglewood. Each summer they have tons of great performances lined up. Plan ahead and get tickets to a musical performance while here in the Berkshires.
Website
U-Drive Boat Rentals

Thanks to U-Drive Boat Rentals, you can enjoy a family trip on a luxurious pontoon boat without the trouble of transportation, maintenance, or gas.
Website
Lanesboro Restaurant & Pizzeria

Serving up Italian fare, including pizza, Lanesboro Restaurant and Pizzeria has been a staple for over 35 years.
Website
Olde Forge Restaurant

Serving the largest selection of imported and domestic beers in the country, Olde Forge Restaurant is a great spot for beer aficionados, or anyone looking for a great burger or other local food.
Website
Tavern at The A

Offering classic American fare alongside late-night food and dancing, this might be just the place you're looking for!
Website
Water Street Grill

Water Street Grill is casual and cozy, offering American food and more than 20 craft brews on tap. Whether you're looking for seafood, burgers, steak, or salad, they have you covered.
Website
There are no attractions to show.