| August |
 | 29 | Tanglewood Jazz Festival. |
 | 30 | Tanglewood Jazz Festival. |
 | 30 | Lenox Chidren's Learning Center Craft Fair in Lilac Park. |
 | 31 | Tanglewood Jazz Festival. |
 | 31 | Lenox Chidren's Learning Center Craft Fair in Lilac Park. |
| September |
 | 12 | A Weekend of the Gilded Age.
The weekend kicks off 7:30pm on Friday evening with “Sarah Morgan’s Soiree” at Ventfort Hall named for the sister of J.P. Morgan, Sarah Morgan, who built Ventfort Hall in 1893. It includes Victorian parlor games, a light buffet of Gilded Age treats, wine, port and mulled cider and, for this special evening, the exhibit “Les Petites Dames de Mode” (The Little Ladies of Fashion) will be open. For an extra special treat, limited access will be granted to Ventfort Hall’s second floor for the first time in decades.
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 | 13 | Tub Parade
On Saturday, the Annual “Lenox Tub Parade” begins at 1 p.m. This recreation of the historic parade of horse drawn carriages (known as tubs) showcases the colors of the season as beautifully decorated carriages, ladies in lavish chapeaus and gentlemen dressed in their coaching finest, parade through the streets of Lenox. An “Ice Cream Social” at Ventfort Hall will immediately follow the parade at approximately 2pm. Ventfort Hall’s “Picnics on the Porch” will be available from 11:30 am to 3pm on the grand Verandah overlooking the sweeping Great Lawn, or visitors may pack a picnic lunch of their own.
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 | 14 | A Weekend of the Gilded Age
The weekend culminates with “Gilded Age Family Picnics” from 10am to 4pm on Sunday at The Mount, Edith Wharton’s Estate and Gardens. Festivities are planned for throughout the day including children’s activities, and visitors are encouraged to bring their own lunches to enjoy a picnic on the stately grounds. The house will be open for touring, as will the gardens, and cider and donuts will be for sale on the Terrace Café.
|
 | 14 | The 32nd Josh Billings Run A-Ground Triathlon. |
 | 19 | Autumn Art Festival. |
 | 20 | Autumn Art Festival. |
 | 21 | Autumn Art Festival. |
 | 26 | Apple Squeeze Folk Art Festival. |
 | 27 | Apple Squeeze Folk Art Festival. |
 | 28 | Apple Squeeze Folk Art Festival. |
| October |
 | 11 | Berkshire Coaching Weekend
Lenox is host to the Great Horse Drawn Carriages of the Victorian Era. Experience the pagentry and beauty of our history as these magnificent coaches and horses ride through Lenox.
10:45AM Carriages drive through Lenox to Shakespeare and Company.
1:15 Return to Orelton Farm |
 | 12 | Berkshire Coaching Weekend
Lenox is host to the Great Horse Drawn Carriages of the Victorian Era. Experience the pagentry and beauty of our history as these magnificent coaches and horses ride through Lenox.
10:45AM Carriages drive through Stockbridge to Norman Rockwell Museum.
1:15 Return to Orelton Farm
|
 | 13 | Berkshire Coaching Weekend
Lenox is host to the Great Horse Drawn Carriages of the Victorian Era. Experience the pagentry and beauty of our history as these magnificent coaches and horses ride through Lenox.
10:45AM Carriages drive through Lenox to The Mount Edith Wharton Estate and Gardens.
1:30 Return to Orelton Farm |