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Berkshires Weekend 2023

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  • Berkshires Weekend 2023
Friday, May 26, 2023 - 8:00am

Please join us for 3-4 days of cycling through the beautiful country 5/26-29

May 26-29, 2023  Bikes, Beers & Ice Cream: Memorial Day Weekend 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.

Please sign the list at the bottom of this webpage, so we can keep you in the loop.

COVID Comments

The COVID pandemic continues. On this weekend, we will be traveling to, from and around New York, Massachusetts and Connecticut. There will be indoor events. Each member should keep abreast of all current regulations and comply with any masking, testing and quarantine regulations that may be in effect. Watch this page, your email and the Message Board for any COVID-related updates.

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, please 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 for a ride for your luggage.
We will be making group reservations on the Metro-North Harlem and Hudson Lines. There will be reserved train rides to Poughkeepsie, Southeast, Dover Plains and/or Wassaic on Friday. From there, you'll continue by bike to the Sheffield/Great Barrington area, and back again on Monday. Watch the Ride Listings and Message Board for the latest updates. You must sign up in the Ride Listings in order to reserve a spot on the train.
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. 

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 local rides Friday and Monday mornings for those who come up early or leave late.

Saturday is our All-Class ride to Lakeville. There won't be any other listed rides on Saturday.

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 Quality Inn (formerly 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 27th:  All-Class Ride to Lakeville

On Saturday, our rides will converge for a picnic lunch at Lake 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. 

En route to Lakeville, the Trinity Church in Lime Rock will again be holding its really delicious bake sale, which usually includes sandwiches, pastries, coffee and other beverages, in addition to a restroom stop.

Lunch can be purchased at the bake sale or at the On-the-Run Coffee Shop in Lakeville, or carried from home

Saturday, May 27th: Saturday Dinner at Barrington Brewery

Our annual NYCC dinner at the Barrington Brewery & Restaurant, 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've arranged a prix-fixe menu of delicious options for omnivores, vegetarians, and vegans. Non-member guests are welcome at our dinner. 

View the menu here.

The price for dinner is $40.00 per person, including taxes and tips. Use the paypal link at the top of this page to sign up for dinner and select your entree. Before you pay, click the Entree for Dinner box and select either Omnivore, Vegetarian, or Vegan from the drop-down menu.

Please register and pay at the PayPal link by Thursday, May 18, 2023 at 12:00 noon.

If you can't register by noon on May 18, feel free to join us individually. Call Barrington Brewery at the number below for reservations and any questions you may have about joining the NYCC group. However, since this is a restaurant, we can't guarantee seating unless you've signed up in advance.

Also, if you're not having dinner, why not come by for drinks and snacks at the bar. No reservations necessary.

Location:  Barrington Brewery & Restaurant, 410 Stockbridge Rd (Rte 7), Great Barrington, MA 01230; 413-528-8282.  

Time:  7:00 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, and continue about 2 miles.

Sunday, May 28th:  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. Some of the restaurants may set up outdoor seating. 

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  ride level 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. At this point, we don't know if anyone will be offering NYCC discounts.

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 "Places 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. Possible NYCC discount--call and ask.

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. Possible 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. 

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

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" on

Sheffield 1802 House | 48 S Main St | Sheffield, MA 01257(413) 248-1145 | | Full breakfast, refrigerator, wi-fi.


If you have any questions, or if anything here needs updating, please write to [email protected] .

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

Berkshires Weekend 2023
cycling trips