DIRT ROADS OF DUTCHESS COUNTY
GALLATIN
White Oak Rd.
Deer Haven Rd.
PINE PLAINS / ANCRAM
Prospect Hill Rd.
Knobb Hill Rd. South (dead end)
Conklin Hill Rd.
Old Conklin Hill Rd.
RED HOOK / MILAN
Freedom La.
Oriole Mills Rd. (eastern half)
Shookville Rd.
Fish Woods Rd.
Wilbur Flats Rd.
Field Rd. (southern end)
Pond Rd. /Silver Lake Rd.
Boice Rd.
CLINTON (South East of Rhinebeck)
Frost / Zippeldburg Rd.
Kansas Rd.
Stonehouse Rd.
Silver Lake Rd.
Lake Drive
Schoolhouse Rd.
Rhynders Rd.
Deer Ridge Drive
Seelbach La.
Walnut La.
Ruskey La. (Steep Hill)
Clinton Ave.
Fox Run
Ward Drive
Sunset Trail
Breezy Hill
Clinton Corners Rd.
Meadowbrook Ln. (east of Walnut)
Halstead (dead end)
Horseshoe Trail
Germond Rd. (dead end)
TOWN OF WASHINGTON
Woodstock Rd.
Petitt Rd.
Canoe Hill Rd.
Fowler Rd.
Shady Dell Rd.
STANFORD / AMENIA
Knight Rd.
North Anson Rd.
Pugsley Hill Rd.
Scheafer Rd.
Flint Hill Rd.
Huckleberry Rd.
Cascade Mountain Rd.
Deep Hollow Rd.
Tower Hill Rd.
Short Rd.
Bonticou Rd. (dead end)
Kennels Rd.
Andrew Haight Rd.
Daheim Rd.
Fraleigh Hill Rd.
Leavitt Rd.
Ludlow Woods Rd.
Yellow City Road (eastern half)
Randalls Rd.
Benton Hill Rd. (uphill into Connecticut)
SUGGESTED RIDES: Start @ corner of Strevers Farm & Bethel Cross Rd., in Pine Plains South to 82 (south), Fork left onto Conklin Hill Rd. (Steep dirt climb) Right onto Carpenter Hill Rd. Left onto 65 Right onto Pugsley Hill Rd. (dirt climb, then descent) Left onto 86 Left onto Separate Rd. Right onto 83 Left onto Flint Hill Rd. (steep dirt climb) Right into Cascade Mountain Rd. (dirt descent) Merge onto 22 south Right onto Deep Hollow Rd. (dirt climb) Left onto Tower Hill Rd. Right at “T”, (still Tower Hill Rd.)(dirt descent) Right onto Short Rd. (dirt) Merge onto 44 (east) Left onto Kennels Rd. (dirt) Left onto Andrew Haight Rd. (dirt) Right onto Mabbettsville (98) Cross Shunpike (57) Left onto Ludlow Woods Rd. (dirt) Right onto Duell Rd. Left onto North Anson Rd. (dirt) Continue on South Anson, becomes Stanford Rd. Cross Shunpike (57) Right onto Woodstock Rd. (dirt) Left onto 82 (south) Left onto Canoe Hill Rd., keep left at fork (becomes dirt) Right onto 44A Left onto 82/44 Right onto Shady Dell (dirt) Right onto South Rd. Right onto Tyrrel Rd. Left onto 44 Right onto Fowler (dirt) Left onto Nardone Right onto 82 (North) Left onto Clinton Corners Rd. (13) Merge with Salt Point Tpk (17) Left onto Clinton Rd. Becomes Schultville Rd. (12) Right onto Clinton Corners Rd. (dirt) Left onto Centre Rd. (18) Left onto Breezy Hill Rd. (dirt) Left onto Sunset Trl (dirt) Right onto Horseshoe Trl (dirt) Right onto Hollow Rd. (14) Cross (18) Left onto Browning Rd. Right onto Ruskey La. (steep dirt climb) Left onto Spooky Hollow Rd. Cross Browning Rd. Proceed on Clinton Ave. (dirt) Bear left onto Fox Run (dirt) Right onto Netherwood (41) Right onto Robinson Rd. Right onto Clinton Ave. Left onto Ward Drive (dirt) Right onto Marshall Rd. Right onto Browning Rd. Right onto Hollow Rd. (14) Left onto Meadowbrook Ln. (becomes dirt) Right onto Seelbach La. (dirt) Left onto Fiddlers Bridge Right onto Browns Pond Rd. (dirt) Right onto Schultz Hill Rd. Right onto Deer Ridge Dr. (dirt) Cross Fiddlers Bridge Stay on Rhynders Rd., bearing left (dirt) Left onto Schoolhouse Rd. (dirt) Right onto Fiddlers Bridge Left onto Lake Drive Left onto Kansas Rd. (dirt climb, then descent) Right onto Slate Quarry (19) Left onto Silver Lake Rd. (dirt) Merge Left onto Milan Hollow Rd. (15) Keep right on Milan Hollow Rd. Right onto 199 Left onto Academy Hill Rd. (51) Right onto Rowe Rd. (dirt) Cross 199 onto Willowbrook La. Right onto Quarfield Rd. Left onto field Rd. (becomes dirt) Left onto Bulls Head (19) Left onto Wendover Rd. Left onto Shelley Hill Rd. Right onto Cold Spring Rd. (53) Short detour right onto Barton La. (dirt) Left onto Stissing, straight on Stissing La to 82 (north) Right onto Old Conklin Hill Rd. (dirt) Right onto Conklin Hill Rd. (dirt climb) Left onto Carpenter Hill Rd. (steep paved descent) Left onto Bethel Cross.
http://www.mapmyride.com/route/us/ny/stanfordville/489126451163594667
http://www.mapmyride.com/route/us/ny/rhinebeck/427126451757253354
http://www.mapmyride.com/route/us/ny/red%20hook/691126451941263255
http://www.mapmyride.com/route/us/ny/clinton/520126548918248646
Stanfordville - 35.4 miles (16.92 miles dirt)
Park @ White Rock Nature Preserve, corner of 82 & Knight Rd.
Proceed up Knight (1st 0.28m paved, then climbs on dirt for 0.64m)
Left onto Anson Rd. (paved for 1.00 mile)
Fork right onto North Anson, then keep left onto dirt section (1.11m dirt)
Right onto Duell (paved 0.96m)
Left onto Ludlow Woods, (uphill dirt 1.93m)
Left onto Shuman Rd. / Right onto Bangall Amenia Rd. (County 86)(paved 2.90m)
Left onto Pugsley Hill Rd. (dirt climb then descent) / Right onto Scheafer Rd. (total dirt 2.77m)
Right onto County 83 (paved 2.14m)
Left onto Flint Hill Rd. (starts paved, steep dirt climb)
At "T" intersection, right onto Cascade Mt. Rd. (steep dirt descent)(total dirt 2.53m)
Right onto 22/343 south through Amenia (4.37 miles paved)
Right onto Deep Hollow Rd. (dirt climb - 3.57 miles)
Left onto 44 (0.58m paved)
Right onto Kennels Rd. (dirt flat, then climb)
Left onto Andrew Haight Rd. (dirt descent) (total dirt 2.30m)
Left onto County 98 (Mabbettsville Rd.)(paved 0.58m)
Right onto Dahein Rd. (dirt climb - 0.43m)
Right onto Bangall Rd. - cross County 57 (Shunpike)(3.56m paved)
Left onto Hammond Rd. (dirt descent then flat ~1.00m)
Right onto Ernest Rd. (paved descent)
Left onto South Anson Rd. (paved - total paved ~2.75m)
Right onto Knight Rd. (dirt descent 0.64m, then paved to finish)

Northern Columbia County - courtesy of Bob Yates
http://www.gmap-pedometer.com/?r=2943638
There is an abundance of dirt roads in Northern Columbia County.

107.6 Mile Road Ride with plenty of dirt and 4629 feet of climbing:
http://www.mapmyride.com/route/us/ny/pine%20plains/625126662904367939