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Berkshires Weekend 2018

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Friday, May 25, 2018 - 8:00am

Please join us for 3-4 days of cycling through the beautiful country 5/25-28

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.  Some of us will cycle from NYC. Others will take a train, and then ride. For more details about rides and lodging, just scroll down.

Social Events

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

Saturday, May 26th:  All-Class Ride to Lakeville

On Saturday, all rides will converge for a picnic lunch at Wononskopomuc (or you can just say “Lakeville”) Lake in CT. Three different routes: the A’s will ride approximately 65 miles, the B’s about 50 miles, the C’s around 40. 

Sandwiches and desserts will be available at the really delicious Trinity Church bake sale where we’ll stop along the way, and the also-delicious On-the-Run Coffee Shop in Lakeville.

Saturday, May 26th:  Dinner at Ski Butternut

Our annual NYCC dinner at Ski Butternut, where we will gather to eat, talk and meet up with old friends and new friends.  We’ll welcome our Berkshires first-timers and share the great experiences of our NYCC Berkshires Weekend.  Vegan-friendly.

We cannot accommodate walk-ins. Advance registration and payment are necessary. The cost is $40 per person, and we'll need your reservations by May 18, 2018 (deadline extended). Please pay via the PayPal link at the top of this page.

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 27th:  Ice Cream Social

Cool off and cool down with the other NYCC members at SoCo Creamery, the Berkshires’ place for amazing award-winning (no kidding!) 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 Day Weekend full of exciting, fun and delicious happenings, from wine and food festivals to summer concerts.

Our Rides

A wide variety of rides will be listed in our Ride Listings, and led by experienced NYCC ride leaders. We’ll probably be adding additional rides until just before the weekend, so keep coming back to the Ride Listings to see what’s new.

There will be rides to and from NYC (~130mi). Other rides will start with a train from Grand Central, followed by a 40-60mi scenic ride from the train to Sheffield/Great Barrington (and back on Monday). There will be short rides Friday and Monday for those who come up early or leave late. Saturday is our all-class ride to Lakeville Lake. Sunday we’ll have 30-80mi rides around the area, including mountains, valleys, and Culture Rides to the Edith Wharton home in Stockbridge. Some rides will be flatter, some will be knee-breakers. Something for everyone.

Where We Will Meet

Most A and B rides start each morning at 9 at the Southern Berkshire School District at 491 Berkshire School Road in Sheffield. (Not to be confused with “The Berkshire School,” which is nearby.) Most C rides will start at the Day’s Inn in Great Barrington.


Participants make their own arrangements for accommodations. Depending on the class of ride you will be doing, you may want to stay near either Sheffield (most A and B rides) or Great Barrington (most C rides).  OTOH, it’s only 7mi from one town to the other, which is a nice warmup if you’re riding to your start point.

Accommodations vary from full service hotels to country inns to B&Bs. Room shares and house shares may be posted on the NYCC Message Board.  

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

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.

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

Mountain View Motel | 304 State Street | Great Barrington, MA 01230 | phone:
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:
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:
Rustic, "chintz free," mountain retreat. Restored 1790s 
timberpeg barn. Country style rooms with baths. Hearty breakfast buffet. Hiking heaven. 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:
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: (Bike storage available in the barn)

Ramblewood Inn | 400 South Undermountain Rd | Sheffield, MA 01257 | phone:
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:
Charming 1850 guest house with 3 lovely rooms set on 2 acres by a quiet country road. 

The Windflower Inn684 South Egremont Road (Route 23) | Great Barrington, MA 01230 |

Historic Inn on 10 acres
 13 rooms with private baths, A/C, wifi, full breakfast, secure bike storage
Close to hiking and biking
search "Windflower"


If you have any questions, please contact Jim Finder

And, please sign up below, so we can keep you in the loop!!

Berkshires Weekend 2018
cycling trips