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Berkshires Weekend 2021

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Friday, May 28, 2021 - 8:00am

Please join us for 3-4 days of cycling through the beautiful country 5/28-31

May 28-31, 2021  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.

There's no charge for anything this year, but please sign the list at the bottom of this webpage, so we can keep you in the loop.

COVID Comments

The Covid interstate travel regulations are constantly changing. On this weekend we will be traveling to, from and around New York, Massachusetts and Connecticut. Each member should keep abreast of all current regulations and comply with any testing and quarantine regulations that may be in effect.

Because of the pandemic, some of the usual Berkshires Weekend events will not take place this year, such as the annual NYCC dinner. We'll organize group rides, following NYCC's Covid guidelines. We may or may not have group train rides. So, watch this page, the Message Board and the Ride Listings for the latest information.

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.


If you’re cycling part of the way, you’ll need to either pack light, or arrange with a driver to carry your luggage. We suggest you use the Message Board to arrange a ride for your luggage.

For the past couple of years, group reservations on the Metro-North Harlem Line have been severely restricted. This year we hope to have reserved train rides to Poughkeepsie, Southeast and Dover Plains on Friday and Monday, which will continue by bike to the Sheffield/Great Barrington area. Watch the Ride Listings and Message Board for the latest updates.
Also, you can ride MNR as individuals. Group reservations are preferred and more reliable, but not strictly required if only a few cyclists are traveling together.  
NYCC members must comply with all MNR regulations. At this writing, masks must be worn at all times on MNR property, regardless of distancing.

Our Rides

A wide variety of A, B and C 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 may 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 may be rides Friday and Monday for those who come up early or leave late.

Saturday is our All-Class ride to Lakeville. For this year only, to reduce crowding and give the leaders more flexibility, there may be listed rides to other destinations as well.

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 29th:  All-Class Ride to Lakeville

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

Sadly, the Trinity Church in Lime Rock will not be holding its really delicious bake sale this year, but we've been invited to stop there along the way for a water and restroom stop. Lunch can be purchased at the On-the-Run Coffee Shop in Lakeville, or carried from home.

Sunday, May 30th:  Outdoor Ice Cream Social

Cool off and cool down with 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 on Railroad Avenue!

Dining Out

A lot of the area dining is centered on Railroad Avenue in Great Barrington, where the restaurants have set up outdoor seating. We encourage NYCC members to dine in that area in the evenings, because we'll be able to mingle (safely) in the street outside, almost as if we were all eating at the same place. 

We have a list of area restaurants, which we are planning to update and distribute to all attendees.

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 around 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 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. 

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 2021
cycling trips