from the roundabout at the west end of the Bear Mountain Bridge, take route 9W North toward Fort Montgomery and West Point (rt 9W in this section sometimes gets high-traffic volumes at high speeds. It has two reasonably wide traffic sections in each direction, but no shoulder, or at most little shoulder, as of 2009. There is also a sidewalk along its east side most of the way thru Fort Montgomery.) Fort Montgomery (food options along rt 9W) Waypoint Right - Old State Rd (variation: to climb less steep, if it's on a time + day with less traffic, we sometimes turn Left on Main St / rt 218 South, then take the entrance ramp onto rt 9W North and do the long climb on the high-speed high-traffic road, sometimes not with very good or very wide shoulder) bear Right - join rt 218 North bear Left - Main St - (food options) (Variation: It's very nice to ride thru West Point / U.S. Military Academy. In the 1990s we used to do it regularly. But now it normally requires official military ID (as of 2008). Sometimes special events or club groups can get permission to ride thru if they request in advance. In that case, try to enter thru the Thayer Gate and exit thru the Washington Gate, and try to get to see two nice views over the river to the east and to the north) Highland Falls Left - rt 218 North / Mountain Av - (opposite Mill St) -- long climb Waypoint (pass by access to Stony Gate of USMA) (pass by road coming from Stony Gate USMA) join rt 9W North - (high-speed high-traffic road, this short section going north-bound had mostly reasonable width of traffic lanes + shoulder, as of 2009) (long climb is over, exit coming up soon) exit Right for rt 218 exit Right for rt 218 + rt 293 (pass by Washington Gate entrance to West Point Military Academy) - (long downhill) (Big viewpoint up and down the Hudson River, and across to Breakneck Ridge. Town south across the river is Cold Spring. If know where to look to the north can see the Skytop point on the Shawangunks ridge.) Cornwall-on-Hudson Right - Dock Hill Rd - (down hill to its end) Waypoint Left - Shore Rd - (or first visit the shore of the Hudson River) (gazebo by the River) (warning: diagonal crossing of railroad tracks -- if not sure how to handle it, dismount and walk bike across) Right - rt 9W North - (high-speed high-traffic road, with reasonable width of traffic lanes + shoulder in this section, except it gets narrower soon crossing bridge over creek -- as of 2009) (food option as of 2009) Right - Old Route 9W, to its end Right - River Rd - (later enters city of Newburgh, becomes Water St) (pass by Renwick St) Right - Washington St quick Left - (Front St) Newburgh (waterfront shops + sidewalk + public toilets -- food is mostly sit-down as of 2009) Waypoint Left - exit from waterfront, short steep climb underneath railroad Right - Water St / Martin Luther King Jr Blvd Right - Grand Av (if reach traffic light, you went too far) go underneath west end of Newburgh-Beacon Bridge. Great view down the river to mountains from the sidewalk on south side of Bridge. That sidewalk goes all the way across the Hudson River to the city of Beacon, which has a Metro North train station Bear Mountain to Newburgh - A 55 60 58 58 59 59 56 53 48 35 43 43 50 50 55 46 52 54 55 52 55 48 46 46 51 50 47 52 50 58 58 51 56 40 55 44 38 43 45 42 42 43 51 55 50 50 50 55 56 56 56 56 56 58 57 57 51 52 50 50 53 61 61 64 64 66 71 91 91 99 99 104 0 106 106 108 123 123 140 140 140 140 143 143 146 165 159 162 161 163 178 0 178 182 187 192 186 187 189 197 189 188 192 193 195 195 195 206 194 210 202 202 197 193 196 196 193 190 176 163 156 157 137 156 135 143 143 143 144 128 150 128 136 118 115 114 108 97 77 78 88 88 69 58 56 84 76 53 52 52 29 75 29 52 83 58 58 47 47 31 82 68 78 78 72 69 69 88 90 77 82 74 79 85 85 94 94 94 125 129 65 108 173 80 126 119 119 154 79 120 82 90 90 87 94 96 96 94 89 85 85 64 60 57 61 57 57 55 52 52 52 52 49 49 50 44 36 27 3 3 15 9 15 15 28 9 10 14 7 14 8 6 12 5 6 6 8 10 10 6 6 6 6 11 11 10 12 15 10 10 33 32 40 32 32 24 10 10 5 5 5 8 8 9 15 9 7 7 8 7 5 9 17 13 8 8 15 5 12 3 6 5 9 13 17 13 27 24 22 33 31 43 56 56 49