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Berkshires Weekend 2020

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Friday, May 22, 2020 - 8:00am

Please join us for 3-4 days of cycling through the beautiful country 5/22-25

May 22-25, 2020  Bikes, Beers & Ice Cream: Join us in the Berkshires


Please join us for 3-4 days of cycling through the beautiful country roads, farmlands and hills of Berkshire County, on NYCC's annual Berkshires Weekend.

Getting There 

Some of us will cycle from NYC. Others will take a train, and then ride from the train. Others will come by car or bus. 
For more information about travel  and lodging, just scroll down.


For the past couple of years, group reservations on the Metro-North Harlem Line have been severely restricted. This year we'll have reserved group train rides to and from Sheffield/Great Barrington on Friday and Monday. Watch the Ride Listings and Message Board for the latest updates.
If you need to travel on your own schedule, you can still ride MNR as individuals, without a group reservation. Last year, several riders took the Harlem Line up to Wassaic without a group reservation, and then cycled from Wassaic to Sheffield. 

Our Rides

A wide variety of rides for NYCC members will be listed in our Ride Listings, 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 may 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 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 cultural sites. Some rides will be flatter, some will be knee-breakers. Something for everyone.

Where Our Rides Meet

Most A and B rides will start at 9am 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.


Social Events

In addition to great rides planned for A, B and C levels (posted in NYCC's Ride Listings), the following social events will also be held:

Saturday, May 23rd:  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, beverges 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 23rd:  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. We’re planning a buffet of delicious options for everyone from omnivores to vegans. Non-member guests are welcome at our dinner. 

We cannot accommodate walk-ins for dinner. Advance registration and payment are necessary. The cost is $40 per person. We'll need your reservations by May 14. Please pay via the PayPal link at the top of this page. Before you pay, click the Choices for Dinner box and select either Unrestricted, Vegetarian, or Vegan from the drop-down menu.

Also, you're welcome to join us before dinner for drinks and snacks only, for a nominal cost of $5.00. No reservations 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 on Route 7 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 (State Road).
- Drive 2 miles on MA 23/183  – follow signs to Butternut. You can't miss it!

Sunday, May 24th:  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.


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).  On the other hand, 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: www.berkshires.orgClick on "Where to Stay” and they’ll give you all kinds of suggestions. Airbnb is another resource.


To share lodgings or automobile rides to, from and within the Berkshires, feel free to post or respond to such posts on the NYCC Message Board. Likewise, if you’re cycling part of the way, you’ll need to either pack light, or arrange with a driver to carry your luggage. Again, please use the 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 Road - Rt.23 East| Great Barrington, MA 01230 | phone: Email [email protected] 
17 units. Cable TV, A/C, phone, refrigerator, kitchenette suite. King beds available. Continental breakfast. Clean rooms.

Monument Mountain Motel | 247 Stockbridge Road, RT 7 | 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 Undermountain 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. In the past there's been a discount for NYCC members. Call them to ask.

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.

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. No avilability in April 2019. Call them to see if they can accept reservations for Memorial Day Weekend.

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 write to [email protected] .

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

Berkshires Weekend 2020
cycling trips