Cycling Climbs in Bennington County

There are 262 cycling climbs in Bennington County.

Peru (19)

Pownal (13)

Readsboro (5)

Rupert (10)

Sandgate (5)

Searsburg (4)

Shaftsbury (22)

South Dorset (6)

Sunderland (27)

Winhall (25)

Woodford (3)

Top 100 Hardest Cycling Climbs in Bennington County

Clicking on the climb category column will toggle between category and difficulty score.

Name	Location	Distance	Avg Gradient	Total Elevation	Climb Category
1. Mt. Equinox Climb (sans car park)	Sunderland	8.48 km	11.5%	976 m	HC
2. Mt. Equinox	Sunderland	8.48 km	11.3%	968 m	HC
3. MtEquinoxRace	Sunderland	8.33 km	11.3%	941 m	HC
4. Mt. Equinox HillClimb	Sunderland	8.46 km	11.1%	943 m	HC
5. Kelly Stand Pass from Arlington	Arlington	17.59 km	3.7%	642 m	Cat. 1
6. RT9 Searsburg W>E	Bennington	14.72 km	3.5%	535 m	Cat. 2
7. Bennington Rte 9 climb	Bennington	12.5 km	3.6%	448 m	Cat. 2
8. Battenkill Bicycles Bromley Climb 2020	Manchester Center	11.66 km	3.8%	438 m	Cat. 2
9. Tollgate to the Top of BIG BROM	Manchester	7.76 km	5.4%	416 m	Cat. 2
10. 1st half Mt Equinox	Sunderland	3.57 km	10.2%	365 m	Cat. 2
11. Guys weekend climb	Manchester	5.96 km	6%	359 m	Cat. 2
12. Dorset Hollow Trail Up	Dorset	5.6 km	6.2%	347 m	Cat. 2
13. 11/30, New Ireland to Top of Bromley	Manchester Center	6.93 km	4.8%	330 m	Cat. 2
14. Windmills Climb (from Rt 9)	Searsburg	10.09 km	2.8%	285 m	Cat. 3
15. Skiparee Climb	Pownal	5.7 km	5%	284 m	Cat. 3
16. Sandgate to Rupert	Sandgate	6.39 km	4.3%	272 m	Cat. 3
17. North Road to Bridge #1	Sunderland	5.82 km	4.4%	256 m	Cat. 3
18. Will koch's delight	Peru	3.42 km	7.1%	243 m	Cat. 3
19. Stratton Mountain entrance to lodge	Winhall	6.22 km	3.9%	290 m	Cat. 3
20. Rupert Mtn from Dorset side	Rupert	3.27 km	7.3%	238 m	Cat. 3
21. Danby road LG-summit full climb	Peru	8.43 km	2.8%	236 m	Cat. 3
22. Kent Hollow Gravel/Dirt (Lang Rd. to Snow Rd.)	Rupert	4.85 km	4.5%	219 m	Cat. 3
23. Maple HIll to East Rd Grinder	Arlington	6.54 km	3.3%	215 m	Cat. 3
24. Tollgate to the Top	Winhall	3.98 km	5.2%	206 m	Cat. 3
25. Rt 8 from 100 to Windmills	Readsboro	4.01 km	5%	202 m	Cat. 3
26. Sleepy Hollow Rd Climb	Searsburg	2.96 km	6.8%	200 m	Cat. 3
27. Tate Hill Rd Climb	Arlington	4.62 km	4.3%	200 m	Cat. 3
28. Stratton Mtn Access Rd to Upper Taylor Hill peak	Winhall	3.33 km	5.7%	189 m	Cat. 3
29. Stratton Access Road (partial)	Winhall	4.83 km	3.9%	187 m	Cat. 3
30. Winhall to 11	Winhall	9.03 km	2%	184 m	Cat. 3
31. Rupert Mtn Climb	Rupert	3.09 km	5.9%	181 m	Cat. 3
32. Mt Anthony Rd Climb	Bennington	2.74 km	6.2%	171 m	Cat. 3
33. Mt Anthony Road Climb Southbound	Bennington	3 km	5.7%	171 m	Cat. 3
34. east rd entire climb	Bennington	6.04 km	2.8%	166 m	Cat. 3
35. Rupert Mtn from Rupert side	Rupert	2.19 km	7.5%	165 m	Cat. 3
36. patpieteralan	Bennington	6.54 km	2.5%	197 m	Cat. 3
37. Brookwood to Dirt	Winhall	1.58 km	10.1%	159 m	Cat. 4
38. Morgan St/ S. Stream	Bennington	9.27 km	1.7%	156 m	Cat. 4
39. Winhall Hollow Old Town Climb	Winhall	4.76 km	3.3%	155 m	Cat. 4
40. Todd Hill - Benson Fuller Climb	Winhall	3.11 km	4.9%	153 m	Cat. 4
41. Readsboro -8 turn	Readsboro	7.65 km	2%	162 m	Cat. 4
42. Rupert Road Climb	Sandgate	3.7 km	4.1%	152 m	Cat. 4
43. Mistral, TO THE TOP	Manchester	2.1 km	7%	147 m	Cat. 4
44. Climb out of Readsboro	Readsboro	3.59 km	4.1%	146 m	Cat. 4
45. E Manchester to a Left	Manchester Center	5.75 km	2.5%	146 m	Cat. 4
46. Molly Stark Trail West	Searsburg	3.13 km	4.6%	144 m	Cat. 4
47. Snow Rd Climb	Rupert	2.43 km	5.9%	142 m	Cat. 4
48. Overpass to Tollgate Road/Mistral	Manchester Center	3.88 km	3.6%	146 m	Cat. 4
49. Stratton Mtn Access Road to Upper Taylor	Winhall	2.07 km	6.6%	138 m	Cat. 4
50. Wall of Death	Manchester	1.66 km	8.2%	137 m	Cat. 4
51. Bentley Hill Road	Sunderland	1.3 km	10.2%	133 m	Cat. 4
52. Branch Pond Access to Summit	Sunderland	3.08 km	4.3%	133 m	Cat. 4
53. Burgess to Gore	Bennington	2.61 km	4.9%	128 m	Cat. 4
54. South Rd - South to North	Winhall	5.03 km	2.5%	127 m	Cat. 4
55. Molly Stark Trail Climb	Woodford	1.38 km	8.7%	120 m	Cat. 4
56. East Road Climb	Shaftsbury	1.89 km	6.2%	118 m	Cat. 4
57. Mad Tom to snowmobile parking lot	Peru	1.7 km	7%	118 m	Cat. 4
58. sandgate notch climb	Sandgate	2.17 km	5.4%	118 m	Cat. 4
59. Up Lower Taylor Hill	Winhall	1.31 km	8.9%	116 m	Cat. 4
60. E Rd Climb	Shaftsbury	2.02 km	5.5%	111 m	Cat. 4
61. Mad Tom Rd Climb	Mount Tabor	2.22 km	5%	110 m	Cat. 4
62. Winhall Hollow/Old Town (Partial)	Winhall	3.5 km	3.1%	108 m	Cat. 4
63. Branch Pond Access Road Climb	Sunderland	1.86 km	5.8%	108 m	Cat. 4
64. Humphrey's Uphill	Dorset	4.26 km	2.5%	106 m	Cat. 4
65. Skiparee Rd Climb	Pownal	1.04 km	10.1%	105 m	Cat. 4
66. Branch Pond Access	Sunderland	3.95 km	2.7%	105 m	Cat. 4
67. Tinkham Rd Climb	Shaftsbury	1.54 km	6.8%	104 m	Cat. 4
68. Kelley Stand Rd Climb	Sunderland	1.95 km	5.3%	104 m	Cat. 4
69. Toll Gate - Underpass to New Ireland	Manchester	1.22 km	8.4%	103 m	Cat. 4
70. Prospect St Climb	Manchester	2.57 km	4%	103 m	Cat. 4
71. Blue Summit Trail Climb	Manchester	0.86 km	11.9%	103 m	Cat. 4
72. South Stream to Barbers Pond	Bennington	10.17 km	1%	102 m	Cat. 4
73. Maple Hill Rd Climb	Arlington	2.34 km	4.3%	101 m	Cat. 4
74. bennington TT first climb	Bennington	8.1 km	1.2%	100 m	Cat. 4
75. Dunnville Natural Rd Climb	Woodford	1.46 km	6.7%	97 m	Cat. 4
76. Michael's Bennington TT	Bennington	17.03 km	0.6%	97 m	Cat. 4
77. 7a S. (313 to Old West Rd)	Arlington	5.46 km	1.7%	94 m	Cat. 4
78. Ore Bed Rd	Bennington	2.87 km	3.2%	92 m	Cat. 4
79. Depot to New Ireland	Manchester Center	3.86 km	2.4%	92 m	Cat. 4
80. bailey hill - up	Readsboro	2.56 km	3.5%	89 m	Cat. 4
81. Sunderland Bacon Climb	Sunderland	3.73 km	2.4%	88 m	Cat. 4
82. NW Hill Rd to Bulkley	Pownal	6.53 km	1.3%	218 m	Cat. 4
83. Morse Hill Rd Rt30 to top of hill	South Dorset	3.67 km	2.3%	85 m	Cat. 4
84. Tate hill	Sandgate	0.98 km	8.7%	85 m	Cat. 4
85. Overlook Gravel Climb	Manchester Center	2.1 km	4%	83 m	Cat. 4
86. Hebron dirt grunt	Rupert	1.78 km	4.7%	84 m	Cat. 4
87. GGT-Krum to the Border	Pownal	1.03 km	8.1%	83 m	Cat. 4
88. Laver Rd Climb	Arlington	1.53 km	5.5%	84 m	Cat. 4
89. Vermont 30 Climb	Winhall	2 km	4.2%	83 m	Cat. 4
90. Mcnamara to Beartown MTB	South Dorset	3.59 km	2.3%	110 m	Cat. 4
91. Fairview St Climb	Bennington	1.19 km	6.9%	82 m	Cat. 4
92. Vermont 11 Climb	Peru	1.77 km	4.6%	81 m	Cat. 4
93. E Rd Climb	Bennington	1.83 km	4.4%	81 m	Cat. 4
94. Vermont 100 Climb	Readsboro	2.32 km	3.5%	81 m	Cat. 4
95. Depot St Climb	Manchester Center	1.73 km	4.7%	81 m	Cat. 4
96. sunderland hill	Sunderland	3.12 km	2.5%	77 m	N/A
97. Burrington Rd	Pownal	3.11 km	2.5%	77 m	N/A
98. Shaftsbury 7A South	Shaftsbury	4.76 km	1.6%	75 m	N/A
99. Hops and Vines Climb	Bennington	1.24 km	5.9%	74 m	N/A
100. Mcnamara MTB climb	South Dorset	1.11 km	6.5%	73 m	N/A

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