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Berkshires Weekend 2017

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Friday, May 26, 2017 - 8:00am

Please join us for 3-4 days of cycling through the beautiful country

Please join us for 3-4 days of cycling through the beautiful country roads, farmlands and of course the Berkshire Mountains on NYCC's annual Berkshires Weekend.  First known as "The Sheffield Weekend," this event has become so popular and grown so much that it is now called "The Berkshires Weekend."  

In addition to a weekend filled with great rides planned for A, B and C levels (see below), the following social events will also be held:

Saturday, May 27th:  Dinner at Ski Butternut

Please join us for our NYCC Dinner at Ski Butternut, where we will gather to eat, talk and meet up with old friends and new friends.  We especially want to welcome our Berkshires first timers and look forward to sharing the great experiences of our NYCC Berkshires Weekend.  

We cannot accommodate walk-ins. Advanced registration and payment by May 22nd is necessary.

Location:  Ski Butternut, 380 State Road, Great Barrington, MA 01230; 413-528-2000

Time:  7:00 p.m. – 10:00 p.m.


- Route 7 North thru the town of Great Barrington
- bear right across the bridge over the Housatonic River at the northern end of town.
- ½ mile from the bridge, make a right at the traffic light onto MA 23/183 South Street
- 2 miles on MA 23/183 stay right on State Street – follow signs to Butternut.
You can't miss it!

Sunday, May 28th:  Ice Cream Social

Cool off and cool down with NYCC members at SoCo Creamery, Berkshires’ place for amazing award-winning ice creams, gelatos and sorbets.  SoCo uses simple and delicious ingredients for recipes made in their very own kitchen.  

Location:  SoCo Creamery, 5 Railroad Avenue, Great Barrington 01230

Time:  9:00 p.m.

*Just show up, grab your own ice cream and hang out

Berkshires Calendar of Events (non-NYCC events)

Don’t forget to check out the local Berkshires Calendar of Events for a Memorial Weekend full of exciting, fun and delicious happenings, from wine and food festivals to summer concerts!

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 in Great Barrington (location TBD).

Riding up on Friday

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


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.  Most A and B rides start each morning at Sheffield High School on Berkshire School Road in Sheffield.  Most C rides will start in Great Barrington (location TBD).  

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

NYCC members have stayed at the following accommodations during the Berkshires Weekends.  This list has no particular order, implies no preferences and by no means includes all possibilities. Shop around.   Services such as Airbnb are another option that can be explored.

Lantern House Motel | 256 Stockbridge Road (Rt 7) | Great Barrington, MA 01230 | phone: 413-528-2350 | Comfortable, bike-friendly motel. See the website for photos. NYCC discount

Mountain View Motel | 304 State Street | Great Barrington, MA 01230 | phone: 413-528-0250 |
17 units. Cable TV, A/C, phone, refrigerator, kitchenette suite. King beds available. Continental breakfast. Clean rooms.

Monument Mountain Motel | 247 Stockbridge Road | Great Barrington, MA 01230 | phone: 413-528-3272 |
17 units (some non-smoking) 1 story AAA motel located on Rt. 7 opposite Friendly's: King beds, queen beds, phones, coffee, heat, A/C, CCTV w/HBO, pool. Close to Tanglewood, arts, golf, skiing and hiking.

Race Brook Lodge | 864 Under Mountain Road (Route 41) | Sheffield, MA 01257 | | phone: 413-229-2916 |
Rustic, "chintz free," mountain retreat. Restored 1790s timberpeg barn. Country style rooms with baths. Hearty breakfast buffet. Hiking heaven. Special group rates through April 14, 2017 (see the Message Board). After April 14, 15% discount for NYCC members

The Wainwright Inn | 518 South Main Street | Great Barrington, MA 01230 | phone: 413-528-2062 | 
Historic 1766 home in town. Wrap-around porches. Fireplaces. A/C. Private baths. Full breakfast. Refreshments. Inquire about children. No pets.

Days Inn | 372 Main Street | Great Barrington, MA, 01230 | phone: 413-528-3150 |

Staveleigh | 59 Main Street | Sheffield, MA 01257 | phone: 413-229-2129 |
Warm and gracious hospitality in circa 1821 home in historic Sheffield. Seven comfortable air-conditioned guest rooms. A splendid breakfast! Near all Berkshires attractions. Open year round.

Berkshire 1802 House | 48 South Main Street | Sheffield, MA 01257 | phone: 413-229-2612 | (Bike storage available in the barn)

Ramblewood Inn | 400 South Undermountain Rd | Sheffield, MA 01257 | phone: 800-854-1862 |
A unique country B&B with style. Serene setting among pines, mountains and lake. Convenient location, swimming, hiking, gourmet breakfasts, pvt. baths, central air., non-smoking. VISA/MC

Orchard Shade | 999 Hewins Street | Sheffield, MA 01257-9668 | phone: 877-672-4233 |
Charming 1850 guest house with 3 lovely rooms set on 2 acres by a quiet country road. 

Birch Hill B&B | 254 South Undermountain Road | Sheffield, MA 01257 | phone: 413-229-2143 


If you have any questions, please email

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Berkshires Weekend 2017

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