Tanglewood Bed and Breakfast

Berkshires Bed & Breakfast

The Fall Season Foliage:
Autumn in the Berkshires is a dazzling kaleidoscope. Of course, the foliage is the focus of this vibrant season, to enjoy while toodling along the back roads, hiking, cycling, picnicking, apple-picking, golfing, exploring historic homes such as The Mount, Naumkeag, Chesterwood or Hancock Shaker Village. After a day in the crisp fall air, come warm up by the fire with a steaming mug of fresh hot cider at our romantic Berkshires Bed and Breakfast.




Berkshire Lakes

Berkshires Bed and Breakfast


The Berkshire hills are alive with brilliant foliage!

Stay two nights, Sunday-Thursday, and save 15%!

Please mention “Leaf-Peeping Special” when making your reservation by phone or online on our website. Not valid with third party gift certificates or for reservations already confirmed.



In Great Barrington at the Mahaiwe Theatre you can watch comedian Rita Rudner perform.  She has been performing throughout Manhattan and on Broadway.

Starting October 1 through October 25, The Colonial Theatre will have the production of “The Homecoming.”  Teddy brings his wife of 6 years, Ruth, to his childhood home in North London to meet his family after a long estrangement.  Their homecoming instigates a power struggle for the ages, and family ties begin to unravel.

The Barrington Stage Company will be performing Veils from October 1 through October 18.   An African American Muslim student arrived in Cairo for a year abroad, where she hopes to finally be understood.  She is quickly enlisted by her liberal Egyptian roommate to help create a controversial blog debating the practice of wearing veils.  Soon mounting political unrest threatens their friendship.

Berkshire’s own astronaut, Stephanie Wilson will talk about her experiences and her career with NASA on Friday, October 2 at 7pm at The Mahaiwe in Great Barrington.

On Saturday, October 3 at 1pm, The Mahaiwee will be having a live screening in HD of “Verdis iL Travatore.”  Soprano Anna Netrebku’s dramatic vocal skills are on full display.

You can watch Shakespeare and Company’s production, An Iliad, between October 3 and November 1.   A modern-day retelling of Homer’s classic tale of gods and goddesses, undying love and endless battles.

On Sunday, October 4th, Berkshire International Film Festival presents a special pre-release screening of “Freeheld” starring Ellen Page, Julianne Moore, and Steve Carell.

Shakespeare and Company will also have a production of Babylon Revisited from October 8 through October 25.  It is a moving story of Charlie Wales and his quest to be reunited with his 9 year old daughter.

Friday, October 9 and Saturday, October 10 at 7:30, The Colonial Theatre in Pittsfield will have a production of Metamorphosis in Evolution of Music.  It will be a fun-filled evening of music and dance.

Friday, October 9 through October 18, Pittsfield will be hosting its 11th Pittsfield City Jazz  Festival.  Six-time Grammy winner, Randy Brecker with the Greg Hopkins Jazz Orchestra will be performing.

Three-time Grammy winner, Lucinda Williams will perform a blend of rock, country, blues, and Americana on Saturday, October 10 at 8pm at The Mahaiwe Theatre in Great Barrington.

The Berkshire Botanical Garden will be hosting its annual Harvest Festival on Saturday, October 10 and Sunday, October 11.  It is a celebration showcasing local crafters and artists, non-stop entertainment, artisan food producers, food trucks, plant and bulb sale, and a farmers market.

You can watch Arlo Guthrie: Alice’s restaurant 50th anniversary tour at The Colonial Theatre on Sunday, October 11 at 7pm.

Have an Intimate Evening with Audra McDonald at The Mahaiwe on Sunday, October 11 at 8pm.