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Escape to The Berkshires this September

Visiting The Berkshires In September
Camille Reddick
Camille Reddick
August 25, 2023

There's no place like the Berkshires at the turn of the season. Visiting the Berkshires in September is a great way to see the landscape while the veil between summer and fall is thin. September is also one of the best months for festivals and events in this slice of New England perfection. Here's a checklist of events to put on your itinerary for an enchanted escape to the Berkshires while the weather is just perfect for gallivanting!

21st Annual "Housatonic Heritage Walks"

People hiking on the Berkshires

This event takes place at rotating sites during every single weekend in September. Heritage Walks are free guided walks through some of the most fascinating sites throughout Berkshire County and Connecticut's Litchfield County. These walks bring attendees through historic, cultural, industrial, and natural places of significance. Here's a glance at some highlights of what's planned for Berkshire-area hikes for the 2023 season:

  1. Hiking to the Keystone Arches Bridges in Becket, MA.
  2. A tour of Great Barrington's architecture and history.
  3. A hike on the Royal Hemlock Trail in Monterey, MA.
  4. A walk through the Shays' Rebellion section of the Appalachian Trail in Sheffield, MA.
  5. Exploration of the perennial plants of Great Barrington.
  6. Family hike in the Pines Community State Forest in Dalton, MA.
  7. Architectural walk at Hancock Shaker Village in Pittsfield, MA.
  8. Walking tour of historic Lee, MA.
  9. Tree identification in Monterey, MA.
  10. Shaker Mountain Hike in Pittsfield, MA.
  11. Exploration of Beartown State Forest in Monterey, MA.
  12. Exploration of the Drury Preserve and Moon in the Pond organic farm in Sheffield, MA.
  13. A hike at the Berkshire Natural Resource Council's Steepletop Reserve.
  14. Walking tour of Lime Kiln Farm Wildlife Sanctuary in Sheffield, MA.
  15. A walking tour of Jacob's Pillow in Becket, MA.

This list represents just a sampling of the many options you can choose from this September! Guests of all ages are invited to attend. If the weather is questionable on the day of a planned walk, it's always a good idea to confirm that a walk is still taking place prior to showing up.

Once Upon a Time in North Berkshire

67th Annual Fall Foliage Parade

Orchestra parading with drums

The theme chosen for this year's highly anticipated festival is Once Upon a Time in North Berkshire! Expect to see floats that bring to life the magic of children's books and fairytales! Taking place on Oct. 1, this is the perfect event to put on your calendar if you'll be visiting the Berkshires for the last official weekend of September. Spectators can find a spot along the 1.2-mile parade route at the intersection of State Street and Old State Street, throughout Main Street, and at the intersection of Ashland Street and Washington Avenue.

The Lenox Apple Squeeze

It doesn't get more New England than this! The 42nd annual Apple Squeeze will return to downtown Lenox on Sept. 23 to deliver homespun fun that will put anyone in a festive state of mind. Taking place from 10 a.m. to 5 p.m. on Saturday, this free event is filled with family fun, live music, street performers, carnival games, and classic fair food! Attendees can even enjoy wagon rides through the picturesque New England town of Lennox.

Ghost Tours at The Mount

The Mount

The Mount is a beautiful country estate in Lenox, Massachusetts that was famously the home of American author Edith Wharton. In 1971, this meticulously designed home became a National Historic Landmark. On Sept. 1, visitors will join experienced tour guides on a two-hour walk through the darkened halls of the estate to explore its eerie lore!

Plan Your Berkshires Fall Getaway

There's nothing quite like visiting the Berkshires in September to help you ease into the "cozy season." Pack your favorite sweater for perfect days spent exploring nature, visiting farm stands, and snagging incredible finds at antique shops. If you're looking for even more things to do in the area, check out this list of free things to do in Pittsfield.