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Berks D1 Pleasantville to Wingdale [Berkshires Weekend]

46.3mi
2,257ft
6.5%
00:00
2,121ft
-8.6%

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Rail trail to Brewster, side roads to Pawling, 55/22 to Wingdale.

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 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: ridewithgps.com/routes/29223938 (starts with a train to Pleasantville) and either of the Day 2 short routes: ridewithgps.com/routes/29223980 (easier) or 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: 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: 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: ridewithgps.com/routes/29223928 (easier - it uses the rail trail from Wassaic to Millerton) or 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.

Author: Carol Waaser

rs 11/27/23
cw - 1/2019

Roboviva Cue Sheet: snuggl.es/roboviva/routes/29223938


Town of Mount Pleasant, NYPublic (346 views)Created Jan 23, 2019Updated Nov 27, 2023Copy of Berks D1 Pleasantville to Wingdale

Surfaces

  • Paved
    46.3 mi
    100%

Cuesheet

  • Exit station parking lot and turn left onto Memorial Plaza
    0.0 mi
  • Turn right onto Bedford Rd
    0.1 mi
  • Continue onto Pleasantville Rd
    0.2 mi
  • Turn right into Briarcliff Manor Library and bear right thru lot
    2.3 mi
  • Turn left onto sidewalk toward picnic pavilion
    2.3 mi
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Ele
Surfaces
Grade
46.3 miles · +2,257 ft / -2,121 ft
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(ft)
1k500
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