Berkshires Weekend

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May 25-28, 2012

As sure as spring turns to summer and the swallows return to Capistrano, the New York Cycle Club descends upon the Berkshire Hills and settles into the small towns of Sheffield, Great Barrington and destinations in between for the Memorial Day holiday weekend.

First known as “The Sheffield Weekend,” this event has become so popular over the years and grown to encompass more of the vicinity that it is now called “The Berkshires Weekend.”

Join us for 3–4 days of cycling through the beautiful country roads, farmland and of course the Berkshire Mountains. Rides are planned for A, B and C levels. 

For our famous Sunday night wrap up dance party and dinner, we are returning to the fabulous Egremont Country Club, a beautiful location just a few miles west of Great Barrington on Rte. 23.  For $45, you get hor d’oeurves, buffet dinner, dessert and dancing (drinks are not included). The registration deadline is May 17th. Don’t miss out on the fun!

Register for the Dinner

Where We Will Meet



Most A and B rides start each morning at Sheffield High School on Berkshire School Road in Sheffield.

Most C rides will start at The Lantern House Motel in Great Barrington.

Information Package

An information package will be sent to everyone the week prior to Memorial Day.

To ensure that each member of your party attending the Berkshires Weekend receives the information packet containing cue sheets and useful details for the weekend, please email [email protected] with the whowhere and email address of everyone in your party.

Knowing the who and where will also help us better plan the weekend.

If you are not planning to join us for the Club dinner, please send your email address to [email protected] so that you can receive the information package.

Ride up on Friday

To maximize your riding opportunities, there will be rides from New York City to the Berkshires using Metro-North train to give us a head start to the country. Please see the ride listings for details of the rides.

Please note:  NYCC will not provide an official luggage shuttle.

If you are planning to join us in the Berkshires by riding up, make sure you have transportation for your luggage, both going up and back.

If you are interested in providing a luggage shuttle, please send an email to [email protected].


Participants make their own arrangements for accommodations. Depending on the class of ride you will be doing, you will want to stay in either Sheffield or Great Barrington (see "Where We Will Meet" above).

Accommodations vary from full service hotels to country inns to B&Bs. To view a list of accommodations, please click here.

Room shares are frequently posted on the NYCC Message Board

Another possibility for lodging:

The Southern Berkshire Chamber of Commerce, 413-528-1510
Hint: click on "Your Guide to Businesses, Attractions & Lodging," then in the input field of the page that opens type "lodging" and click "Execute Search".

To share lodgings or automobile rides to the Berkshires, feel free to post or respond to such posts on the NYCC Message Board or email [email protected] and we will try to match people up.

cycling trips