Come join us in the Berkshires February 20 – 22nd in the charming town of Lenox MA. This will be a Winter Experience like no other! It will be a weekend filled with live jazz, Gilded Age venues and plenty of fun to transport you back to the Prohibition Era.
We have two lodging options this year. We have limited space at the site of our Friday night private party at Berkshires Untold. Additional lodging can be found at the Holiday Inn. Each room comes with two queen beds unless otherwise noted.
During the daytime you have the option to go skiing at Catamount resort, located just over the border in Hillsdale NY. Not interested in the slopes? We will have a scavenger hunt planned that will empower you to explore all the places to see in Lenox.
What makes this trip different than previous ones? We are renting out a Gilded Age Mansion for our exclusive Saturday night party… Ventfort Hall! This building is listed on the National Register of Historic Places! What makes this trip even more exclusive? We can only accommodate 75 people in the mansion. The building is a living museum, and they can only allow so many people into it. Its ongoing renovations only allow a small quantity of people in. As a result, space is limited. Not sold on this weekend yet? See the weekend itinerary below.
You coming….old sport?
Friday – February 20, 2026
Private “Welcome to the Prohibition Era” Party at Berkshires Untold. This curated and stylish hotel will allow you to step back in time. Break out your best vintage outfit and meet the rest of the party goers!
February 21, 2026
Daytime: Hit the slopes or explore Lenox, you choose! Skiers & riders can enjoy the slopes at Catamount (added fee), just 30 minutes away from Lenox. Never been to the Berkshires? Don’t miss our Scavenger Hunt to explore all the sites!
Nighttime: Get ready for a night to remember as we transform Ventfort Hall into our exclusive Saturday night party! This will be epic!
Cocktails start at 6pm, with a dinner buffet at 7. After dinner, dance instructors Jennifer & Roman (above) will lead the group in a group dance lesson before our live Jazz band comes on stage for the rest of the night where you can dance the night away! Don’t want to dance? Come see your future with our Tarot card reader. Want to explore the Mansion? Take pictures in all it’s glory with fellow party goers!
Gilded Age Mansion Ventfort Hall will be our exclusive private party location Saturday night. |
Your Gatsby Weekend Includes:
* 2 nights hotel lodging in Lenox MA.
* Friday night party entrance at Berkshires Untold
* Free Saturday buffet dinner
* Group jazz dance lesson
* Saturday night party entrance to Ventfort Hall with live jazz band
* Free Saturday night van transportation to/from Ventfort Hall.
* On site staff to assist your needs
* All taxes
** Catamount lift tickets are available at an additional cost.
Pricing:
Holiday Inn
Quad (Two queen beds/4 to a room): $335 per person
Triple: $365 pp
Double: $425 pp
Berkshires Untold (Very Limited Space)
Quad: $350 per person
Triple: $380 pp
Double: $475 pp
There are only 75 spaces available on this trip. So do not hesitate! Click the button below to book your weekend now!