As we come out of our long hibernation we’ve decided to seek some of the great joys in our own backyard. Some of us remember when E.C. Grayson used to organize grand evenings of music and fun in New York every couple of years. Castles and Concerts has decided that this is the perfect time to revive this grand tradition of gathering on the East Coast. We will start with a magnificent party in the very heart of Manhattan’s most prestigious neighborhood before heading up to New England for a week of music, local culture, gala dinners and camaraderie among one of nature’s finest shows: the fall foliage in New England.
New York City
The Berkshires
Our destination will be the charming town of Stockbridge, Massachusetts, the home of the quintessential American artist: Norman Rockwell. During our visit here, we’ll have nightly parties with music featuring your favorite Castles and Concerts performers, right alongside some amazing local talent that we can’t wait to share with you. The surrounding areas offer an abundance of culture, history, and natural beauty that we will explore in depth over the next six days.

New York City

Before our journey up the Hudson to the Berkshires, we’ll arrive in New York to open up our trip in style. We’ll be staying at The Pierre, a famous luxery hotel at the corner of 61st and Fifth, facing Central Park. Our rooms will feature all of the amenities one can expect from one of the finest luxury hotels in Manhattan.

Right around the corner from The Pierre is The Metropolitan Club, one of them most exclusive private clubs in NYC.  We are so excited to have our Opening Gala Dinner and Show on Sunday, October 17.  We'll start the evening with an amazing concert featuring some of the best New York City has to offer, including a few great local jazz artists, a couple of Broadway stars and some of your favorite Castles and Concerts entertainers.  After the show, we'll have a wonderful dinner and if that's not enough for you, we'll cap off the night with some dancing in the grand ballroom.

The Metropolitan Club Foyer
The Pierre Hotel
If you have a home in New York, plan on staying with friends, or have another hotel that you prefer, Castles and Concerts will gladly deduct the cost of The Pierre. Additionally, we are happy to extend invitations to any friends or family of yours on the east coast that would like to join us for an evening of music, fine food, and revelry.

Journey to The Berkshires

The Hudson River in the Fall
After our opening gala, Castles and Concerts has chartered The Manhattan II, a white-hulled 100-foot long & 22-foot beam yacht to travel up the Hudson River and into Massachusetts. We’ll have lunch on board, and more likely than not, some impromptu music-making will break out as we take in the sights of the river.
Red Lion Inn (est 1773)
Our home in the Berkshires will be the historic Red Lion Inn, nestled in the heart of Stockbridge. This landmark inn was built in 1773. In 1776, they had to change the name of the bar from the King George Tavern to the George Washington Tavern. It was badly damaged by fire in 1892 and in the rebuild they added electricity and modern plumbing. It has been refurbished many times but it retains all the charm and much of the decor of its historic past. We’ll spend our days here exploring the magnificent and historic countryside by day and feasting and making music in the evenings.
While in Stockbridge, we’ll have an abundance of cultural and historical landmarks, as well as areas of unreal natural beauty, all within a very short distance of our hotel. We’ll visit and tour The Mount, the grand home of American novelist Edith Wharton. The entire estate was designed as a complete work of art, informed by French, Italian and English traditions, yet adapted for the American landscape.

Norman Rockwell spent the last 25 years of his life in Stockbridge, and many of the people and places, including our hotel, were featured in his works. We’ll visit The Norman Rockwell Museum, which is dedicated to his work and life.

The Mount, Edith Wharton's Home
Pleasant Valley Wildlife Sanctuary
Though the stupendous fall foliage will be a constant backdrop for our journey, we’ve found a couple of particularly majestic locations where the natural beauty seems to be amplified to an even greater degree. The Pleasant Valley Wildlife Sanctuary is one such place. The sanctuary features easy walks around a pond, along with optional hiking up into the surrounding hills. There are also very active beaver colonies that can be frequently spotted. We are also arranging tours of some local botanical gardens that highlight the local flora and fauna.

Details and Costs

We hope that you will consider joining us for the entire week-long adventure starting with a stay at The Pierre Hotel, the gala dinner and show at the Metropolitan Club in New York City, then on to our riverboat cruise up the Hudson River and ultimately for six days and nights of music, laughter, camaraderie, local culture and gastronomic delights in and around the Red Lion Inn in Stockbridge, Mass. If you come for the whole week, then everything is included for the sum of $6,750 per person. This includes both hotels, breakfast and dinners (with wine/beer). In addition, lunch is included each day with the small group excursions that we organize. The only thing that you will be on the hook for are drinks that you sign for at the bar.
Central Park in the Fall
Red Lion Inn in winter, as painted by Norman Rockwell
We have structured this adventure so that you can join in whatever part best suits your schedule. For our opening night, we’ll have entertainers from both coasts in one of the finest venues in New York with an open bar with premium drinks and wines. We’ve covered all the many fees, taxes and gratuities. The cost to attend this party is $650/person.  Please invite your NYC friends to join us.  If you would like for us to make hotel arrangements for you, we will set-aside a room for you at The Pierre Hotel for $785/night, including all taxes and fees. You are, of course, free to arrange your own lodging if that works best for you.

If you’d rather skip the grand festivities in New York and just join us Monday at the Red Lion Inn in Stockbridge, we will deduct the NYC costs ($2,085 for a couple) from the total cost of the trip which works out to $5707.50/person.

Arrival: We’ll start the party on Sunday, October 17 at 6:30 pm.  Please be aware that the three-hour time difference means that you need to catch an early morning flight from the West Coast in order to arrive in time to check-in and get ready for the party.  If you would like to fly in a day or two earlier, we are happy to get you a room at The Pierre.  We do have a limited number of suites available, so please let us know if you are interested in an upgraded room.
Departure: We will run separate coaches in the morning from the Red Lion Inn to Newark Liberty (EWR) and JFK airports on Sunday, October 24 at 8:00 am. With light traffic on Sunday morning, it should be less than three hours to either airport. There are several afternoon flights back to the Bay Area and the three hour time difference works in our favor on the way home.

Dress: For our party in New York City, please dress as fancy as you please or as fancy as you dare. At the Red Lion Inn, we will be casual. Men can wear jackets but ties are very optional.

Weather: We are trying to hit the absolute peak of the autumn colors. This means beautiful daytime weather and cool enough for a jacket in the evenings. This is not a rainy season, but it’s always a possibility. Be sure to bring some comfortable sneakers or shoes so that you can take at least one of the beautiful nature walks that we’ve picked out.

We are so excited to travel with all of our friends again, and we hope that you’ll consider joining us one what is sure to be a memorable trip!

Central Park, steps away from our hotel
Dining Room at The Metropolitan Club


Please feel free to email or call us with any questions you may have. Thank you.


(650) 444-3934
(661) 803-2098
(415) 492-1059