Nothing feels as much like fall as picking apples and viewing the colorful fall foliage in Massachusetts. But how would you like to make a weekend trip of it? Go apple picking, and spend the night in a cabin with colorful views on this weekend getaway in Massachusetts in the fall. You’ll love your time away this fall in the Berkshires.

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Are you ready for a fall weekend getaway in Massachusetts? We’re certainly ready! What is your favorite fall activity besides apple picking in Massachusetts? Let us know in the comments. Keep up with updates at Jaeschke’s Orchard. Be sure to book your stay at Rose and Goat Retreat, and follow the retreat on Facebook for updates and photos.

If you love taking day trips, head out to one of these beautiful fall destinations in Massachusetts. Sounds like it’s time for a road trip in Massachusetts!

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More to Explore

Things To Do In Massachusetts

Hidden gem attractions in Massachusetts include:

  • Castle Hill at the Crane Estate in Ipswitch. Gorgeous gardens are combined with stunning ruins and ocean views to make this an unforgettable destination.
  • The Brattle Bookshop in Boston. This is one of the oldest antiquarian bookshops in the nation, which opened in 1825. 
  • Bancroft Tower Castle in Worcester. This castle was built in 1900 to memorialize George Bancroft who was born at this place in 1800.
  • Stockbridge General Store in Stockbridge. Norman Rockwell used this as inspiration for several of his paintings and it is replete with New England charm.

Discover more about these and other hidden gem attractions in Massachusetts

What are the most scenic backroads in Massachusetts?

The most scenic backroads in Massachusetts include:

  • Central Hills Loop. This drive provides awe-inspiring views of the Quabbin Reservoir with serene waters and lush forests.
  • Cape Ann Shore. The road here offers coastal views of not just the water, but of charming lighthouses with free whiffs of salt air.
  • Route 6A. Locally known as the Old King’s Highway, this was the royal route when this area was being colonized and it is lined with historic buildings.
  • Route 20. Also knowns as Jacob’s Ladder Scenic Byway, this road winds through the Berkshire foothills and through the charming town of Lee.

Find out more about the most scenic backroads in Massachusetts

What are the most amazing historical landmarks in Massachusetts?

The most amazing historical landmarks in Massachusetts include:

  • Minute Man National Historical Park. This is where the Battle of Concord and Lexington took place during the Revolutionary War.
  • Plymouth Rock. This is said to be the place where America got its start as the landing point of the first pilgrims.
  • Veterans War Memorial. Located at Mount Greylock State Reservation, this is the highest point in the state and remembers those who gave their all for this state and country.
  • Old State House. Located in Boston, this is the oldest standing structure in Boston and is the site where the Boston Massacre took place.

Learn more about the most amazing historical landmarks in Massachusetts.