[Berkshire Weekend] Self-Contained to the Berkshires

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  • [Berkshire Weekend] Self-Contained to the Berkshires
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General Information
Way Points: 

Option 1.) Day 1: Pleasantville > N County Rail Trail > Putnam Rail Trail > Brewster > Wingdale. Day 2: Wingdale > Sharon > Millerton > Salisbury > Sheffield > Great Barrington

Option 2.) Day 1: Bronx > S & N County Rail Trails > Putnam Rail Trail > Brewster. Day 2: Brewster > Pawling > Wingdale > Dover Plains > Wassaic > Rail Trail > Millerton > Salisbury > Sheffield > Great Barrington

Option 3.) Day 1: Bronx > back roads to Bedford > back roads thru Salem > Brewster. Day 2: Brewster > Sherman > Kent > Sharon > Salisbury > Sheffield > Great Barrington

Interest Tags: 
Carol Waaser
Signature Route : 
Region Name(s): 
Multi-Day Tours, The Berkshires
A, B, C
Vertical Gain: 
Difficulty Rating: 
3 out of 5
Attached Files

Memorial Day Weekend in the Bershires is a club favorite, but why not take an extra day off and make it a real adventure. Leave on Thursday and go half-way, staying in a motel or B & B overnight. Then ride the rest of the way on Friday and meet up with everyone else in Sheffield or Great Barrington. I've put together several options so that any level of rider can do this. You can choose the short & easy routes (what I think of as the C routes), or a longer but still not too difficult version (the lower level B routes) or the longer, quite hilly version (the upper B and A routes). All routes are scenic.

This kind of "self-contained" tour can easily be done on a road bike. You only need to carry clothes & essentials for one overnight; send the rest of your things in a small bag with someone who's driving. You can use a seatpost rack and small panniers or large rack pack or a large seat bag, such as a Carradice - it won't even weigh you down too much. See https://nycc.org/rides/touring-tips for more info on using a road bike for short tours.

For C riders, I recommend the Day 1 Short & Easy route: https://ridewithgps.com/routes/29223938 (starts with a train to Pleasantville) and either of the Day 2 short routes: https://ridewithgps.com/routes/29223980 (easier) or https://ridewithgps.com/routes/29223957 (a little hillier but still fairly easy). You'll find the Dutchess Motor Lodge on Rte. 22 in Wingdale or use Google Maps to find other lodging in the area

B and A riders can also mix & match the Bronx to Brewster to Great Barrington routes. Day 1 Longer & Easy: https://ridewithgps.com/routes/29223899 (this starts at the 231st St Station of the #1 train, where there's an elevator, and goes up the rail trails) or Day 1 Longer & Hilly: https://ridewithgps.com/routes/29223904 (this starts at the Kingsbridge Rd station of the D train, where there's an elevator, and uses a portion of the B-SIG Deep Westchester Route). Then use either of the Day 2 long routes: https://ridewithgps.com/routes/29223928 (easier - it uses the rail trail from Wassaic to Millerton) or https://ridewithgps.com/routes/29223915 (hillier - this uses the old B-17 route from Brewster on up). You can overnight at the Bel Aire Motor Lodge on Rte. 22 in Sears Corner, just north of Brewster or find other lodging in the area - there's a lovely B & B in Pawling.

cw - 1/2019

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